Abstract

The synthesis, chemical characterization and nonlinear optical properties of a family of soluble thallium(III) phthalocyanine(Pc) halide complexes are reported. Tl(t-Bu4Pc)X (X = Cl, Br, or I) were made from 4-t-butylphthalonitrile via oxidation of a dithallium(I) phthalocyanine complex and were characterized by elemental analysis, spectroscopy (UV-vis, 1H NMR and X-ray fluorescence) and MALDI-TOF mass spectrometry. Transient white light absorption measurements of the iodo complex in toluene showed a broad band (440 – 610 nm) excited state absorption with a multiexponential decay dominated by species with lifetimes of ~4.8 ± 1 ps and > 20 ns. The ratio of the long lived excited state absorption coefficient to that of the ground state is ~100 at 500 nm. Nonlinear transmission and Z-scan experiments (532 nm, f5 optics) confirmed the above and also showed that the real part of the nonlinear refractive index is negative.

© 2015 Optical Society of America

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    [Crossref]
  3. J. S. Shirk, J. R. Lindle, F. J. Bartoli, C. A. Hoffman, Z. H. Kafafi, and A. W. Snow, “Off-Resonant 3rd-Order Optical Nonlinearities of Metal-Substituted Phthalocyanines,” Appl. Phys. Lett. 55(13), 1287–1288 (1989).
    [Crossref]
  4. M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “3rd-Order Nonlinear Optical-Properties in Soluble Phthalocyanines with Tert-Butyl Substituents,” Jpn. J. Appl. Phys. 30(8), 1715–1719 (1991).
    [Crossref]
  5. J. S. Shirk, J. R. Lindle, F. J. Bartoli, Z. H. Kafafi, A. W. Snow, and M. E. Boyle, “Third-Order Nonlinear Optical Properties of Metallo-Phthalocyanines,” Int. J. Nonlinear Opt. Phys. 1(04), 699–726 (1992).
    [Crossref]
  6. J. W. Perry, K. Mansour, S. R. Marder, K. J. Perry, D. Alvarez, and I. Choong, “Enhanced Reverse Saturable Absorption and Optical Limiting in Heavy-Atom-Substituted Phthalocyanines,” Opt. Lett. 19(9), 625–627 (1994).
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  10. K. Mansour, J. D. Alvarez, K. J. Perry, I. Choong, S. R. Marder, and J. W. Perry, “Dynamics of optical limiting in heavy-atom substituted phthalocyanines,” Proc. SPIE 1853, 132–141 (1993).
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  15. E. A. Cuellar and T. J. Marks, “Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyanines,” Inorg. Chem. 20(11), 3766–3770 (1981).
    [Crossref]
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    [Crossref]
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    [Crossref]
  27. A. R. Monahan, J. A. Brado, and A. F. Deluca, “Association of copper(II), vanadyl, and zinc(II) 4,4′,4″,4″-tetraalkylphthalocyanine dyes in benzene,” J. Phys. Chem. 76(14), 1994–1996 (1972).
    [Crossref]
  28. A. R. Monahan, A. F. Deluca, and J. A. Brado, “Dimerization of a copper(II)-phthalocyanine dye in carbon-tetrachloride and benzene,” J. Phys. Chem. 76(3), 446–449 (1972).
    [Crossref]
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    [Crossref]
  30. R. D. George, A. W. Snow, J. S. Shirk, and W. R. Barger, “The alpha substitution effect on phthalocyanine aggregation,” J. Porphyr. Phthalocyanines 2(01), 1–7 (1998).
    [Crossref]
  31. D. D. Dominguez, A. W. Snow, J. S. Shirk, and R. G. S. Pong, “Polyethyleneoxide-capped phthalocyanines: limiting phthalocyanine aggregation to dimer formation,” J. Porphyr. Phthalocyanines 5(07), 582–592 (2001).
    [Crossref]
  32. M. Hanack, T. Schneider, M. Barthel, J. S. Shirk, S. R. Flom, and R. G. S. Pong, “Indium phthalocyanines and naphthalocyanines for optical limiting,” Coord. Chem. Rev. 219, 235–258 (2001).
    [Crossref]
  33. J. S. Shirk, J. R. Lindle, S. R. Flom, F. J. Bartoli, and A. W. Snow, “3rd-Order Nonlinear Optical-Properties of Phthalocyanines,” in Electrical, Optical, and Magnetic Properties of Organic Solid State Materials, L. Y. Chiang, A. F. Garito, and D. J. Sandman, eds. (Mater. Res. Soc.Symp. Proc. 247, Pittsburgh, PA, 1992), pp. 197–201.
  34. J. S. Shirk, R. G. S. Pong, F. J. Bartoli, and A. W. Snow, “Optical limiter using a lead phthalocyanine,” Appl. Phys. Lett. 63(14), 1880–1882 (1993).
    [Crossref]
  35. M. J. Soileau, T. H. Wei, M. Sheikbahae, D. J. Hagan, M. Sence, and E. W. Vanstryland, “Nonlinear optical characterization of organic materials,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 207(1), 97–101 (1991).
    [Crossref]
  36. M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. VanStryland, “Sensitive measurement of optical nonlinearities using a single beam,” IEEE J. Quantum Electron. 26(4), 760–769 (1990).
    [Crossref]
  37. B. L. Justus, A. L. Huston, and A. J. Campillo, “Broad-band thermal optical limiter,” Appl. Phys. Lett. 63(11), 1483–1485 (1993).
    [Crossref]
  38. J. S. Shirk, R. G. S. Pong, S. R. Flom, H. Heckmann, and M. Hanack, “Effect of axial substitution on the optical limiting properties of indium phthalocyanines,” J. Phys. Chem. A 104(7), 1438–1449 (2000).
    [Crossref]

2006 (1)

P. W. Ayers, R. G. Parr, and R. G. Pearson, “Elucidating the hard/soft acid/base principle: A perspective based on half-reactions,” J. Chem. Phys. 124(19), 194107 (2006).
[Crossref] [PubMed]

2005 (1)

D. Dini, M. J. F. Calvete, M. Hanack, W. Z. Chen, and W. Ji, “Synthesis of axially substituted gallium, indium and thallium phthalocyanines with nonlinear optical properties,” ARKIVOC 2006(3), 77–96 (2005).
[Crossref]

2002 (1)

P. D. Huffman, J. P. Fitzgerald, and J. S. Shirk, “New lead and thallium phthalocyanines as optical limiting materials,” Abstracts Am. Chem. Soc. 223, U238(2002).

2001 (2)

D. D. Dominguez, A. W. Snow, J. S. Shirk, and R. G. S. Pong, “Polyethyleneoxide-capped phthalocyanines: limiting phthalocyanine aggregation to dimer formation,” J. Porphyr. Phthalocyanines 5(07), 582–592 (2001).
[Crossref]

M. Hanack, T. Schneider, M. Barthel, J. S. Shirk, S. R. Flom, and R. G. S. Pong, “Indium phthalocyanines and naphthalocyanines for optical limiting,” Coord. Chem. Rev. 219, 235–258 (2001).
[Crossref]

2000 (2)

J. S. Shirk, R. G. S. Pong, S. R. Flom, H. Heckmann, and M. Hanack, “Effect of axial substitution on the optical limiting properties of indium phthalocyanines,” J. Phys. Chem. A 104(7), 1438–1449 (2000).
[Crossref]

J. S. Shirk, “Protecting the Warfighter's Vision In a Laser-rich, Battlefield Environment,” Optics and Photonics News 11(4), 19–23 (2000).
[Crossref]

1999 (1)

T. Suga, S. Isoda, and T. Kobayashi, “Characterization and electrical conductivity of dithallium phthalocyanine (Tl2Pc),” J. Porphyr. Phthalocyanines 3(06), 397–405 (1999).
[Crossref]

1998 (3)

K. Schweiger, H. Hueckstaedt, and H. Homborg, “Iodophthalocyaninato(2–)thallium(III) – Synthese und Kristallstruktur,” Z. Anorg. Allg. Chem. 624(2), 167–168 (1998).
[Crossref]

W. J. Su, T. M. Cooper, and M. C. Brant, “Investigation of reverse-saturable absorption in brominated porphyrins,” Chem. Mater. 10(5), 1212–1213 (1998).
[Crossref]

R. D. George, A. W. Snow, J. S. Shirk, and W. R. Barger, “The alpha substitution effect on phthalocyanine aggregation,” J. Porphyr. Phthalocyanines 2(01), 1–7 (1998).
[Crossref]

1996 (1)

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

1994 (1)

1993 (5)

K. Mansour, J. D. Alvarez, K. J. Perry, I. Choong, S. R. Marder, and J. W. Perry, “Dynamics of optical limiting in heavy-atom substituted phthalocyanines,” Proc. SPIE 1853, 132–141 (1993).
[Crossref]

M. Hanack, D. Y. Meng, A. Beck, M. Sommerauer, and L. R. Subramanian, “Separation of structural isomers of tetra-tert-butylphthalocyaninatonickel(II),” J. Chem. Soc. Chem. Commun. 1993(1), 58–60 (1993).
[Crossref]

B. L. Justus, A. L. Huston, and A. J. Campillo, “Broad-band thermal optical limiter,” Appl. Phys. Lett. 63(11), 1483–1485 (1993).
[Crossref]

J. S. Shirk, R. G. S. Pong, F. J. Bartoli, and A. W. Snow, “Optical limiter using a lead phthalocyanine,” Appl. Phys. Lett. 63(14), 1880–1882 (1993).
[Crossref]

J. Janczak and R. Kubiak, “Crystal and molecular-structure of dithallium phthalocyanine At 300-K,” J. Alloys Compd. 202(1-2), 69–72 (1993).
[Crossref]

1992 (2)

J. S. Shirk, J. R. Lindle, F. J. Bartoli, Z. H. Kafafi, A. W. Snow, and M. E. Boyle, “Third-Order Nonlinear Optical Properties of Metallo-Phthalocyanines,” Int. J. Nonlinear Opt. Phys. 1(04), 699–726 (1992).
[Crossref]

T. H. Wei, D. J. Hagan, M. J. Sence, E. W. Vanstryland, J. W. Perry, and D. R. Coulter, “Direct measurements of nonlinear absorption and refraction in solutions of phthalocyanines,” App. Phys. B-Photophys, Laser Chem. 54, 46–51 (1992).

1991 (2)

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “3rd-Order Nonlinear Optical-Properties in Soluble Phthalocyanines with Tert-Butyl Substituents,” Jpn. J. Appl. Phys. 30(8), 1715–1719 (1991).
[Crossref]

M. J. Soileau, T. H. Wei, M. Sheikbahae, D. J. Hagan, M. Sence, and E. W. Vanstryland, “Nonlinear optical characterization of organic materials,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 207(1), 97–101 (1991).
[Crossref]

1990 (1)

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. VanStryland, “Sensitive measurement of optical nonlinearities using a single beam,” IEEE J. Quantum Electron. 26(4), 760–769 (1990).
[Crossref]

1989 (2)

D. R. Coulter, V. M. Miskowski, J. W. Perry, T.-H. Wei, E. W. Van Stryland, and D. J. Hagan, “Optical Limiting In Solutions Of Metallo-Phthalocyanines And Naphthalocyanines,” Proc. SPIE 1105, 42–51 (1989).
[Crossref]

J. S. Shirk, J. R. Lindle, F. J. Bartoli, C. A. Hoffman, Z. H. Kafafi, and A. W. Snow, “Off-Resonant 3rd-Order Optical Nonlinearities of Metal-Substituted Phthalocyanines,” Appl. Phys. Lett. 55(13), 1287–1288 (1989).
[Crossref]

1984 (1)

A. W. Snow and N. L. Jarvis, “Molecular association and monolayer formation of soluble phthalocyanine compounds,” J. Am. Chem. Soc. 106(17), 4706–4711 (1984).
[Crossref]

1982 (2)

M. Hanack, J. Metz, and G. Pawlowski, “Soluble trans-di-1-alkynyl(tetraalkylphthalocyaninato)metal and poly-trans-ethynyl(tetraalkylphthalocyaninato)metal IVB Derivatives,” Chem. Ber. 115, 2836–2853 (1982).
[Crossref]

C. C. Leznoff and T. W. Hall, “The synthesis of a soluble, unsymmetrical phthalocyanine on a polymer support,” Tetrahedron Lett. 23(30), 3023–3026 (1982).
[Crossref]

1981 (1)

E. A. Cuellar and T. J. Marks, “Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyanines,” Inorg. Chem. 20(11), 3766–3770 (1981).
[Crossref]

1972 (2)

A. R. Monahan, J. A. Brado, and A. F. Deluca, “Association of copper(II), vanadyl, and zinc(II) 4,4′,4″,4″-tetraalkylphthalocyanine dyes in benzene,” J. Phys. Chem. 76(14), 1994–1996 (1972).
[Crossref]

A. R. Monahan, A. F. Deluca, and J. A. Brado, “Dimerization of a copper(II)-phthalocyanine dye in carbon-tetrachloride and benzene,” J. Phys. Chem. 76(3), 446–449 (1972).
[Crossref]

1971 (1)

S. A. Mikhalenko, S. V. Barkanova, O. L. Lebedev, and E. A. Lukyanets, “Phthalocyanines and related compounds IX. Synthesis and Electronic Absorption Spectra of tetra-4-t-butylphthalocyanines,” J. Gen. Chem. USSR 41, 2770–2773 (1971).

1970 (1)

Z. A. Schelly, D. J. Harward, P. Hemmes, and E. M. Eyring, “Bonding in dye aggregates - energetics of dimerization of aqueous cobalt(II)-4,4′,4″,4‴-tetrasulfophthalocyanine ion,” J. Phys. Chem. 74(16), 3040–3042 (1970).
[Crossref]

1963 (1)

R. G. Pearson, “Hard and soft acids and bases,” J. Am. Chem. Soc. 85(22), 3533–3539 (1963).
[Crossref]

Alvarez, D.

Alvarez, J. D.

K. Mansour, J. D. Alvarez, K. J. Perry, I. Choong, S. R. Marder, and J. W. Perry, “Dynamics of optical limiting in heavy-atom substituted phthalocyanines,” Proc. SPIE 1853, 132–141 (1993).
[Crossref]

Ayers, P. W.

P. W. Ayers, R. G. Parr, and R. G. Pearson, “Elucidating the hard/soft acid/base principle: A perspective based on half-reactions,” J. Chem. Phys. 124(19), 194107 (2006).
[Crossref] [PubMed]

Barger, W. R.

R. D. George, A. W. Snow, J. S. Shirk, and W. R. Barger, “The alpha substitution effect on phthalocyanine aggregation,” J. Porphyr. Phthalocyanines 2(01), 1–7 (1998).
[Crossref]

Barkanova, S. V.

S. A. Mikhalenko, S. V. Barkanova, O. L. Lebedev, and E. A. Lukyanets, “Phthalocyanines and related compounds IX. Synthesis and Electronic Absorption Spectra of tetra-4-t-butylphthalocyanines,” J. Gen. Chem. USSR 41, 2770–2773 (1971).

Barthel, M.

M. Hanack, T. Schneider, M. Barthel, J. S. Shirk, S. R. Flom, and R. G. S. Pong, “Indium phthalocyanines and naphthalocyanines for optical limiting,” Coord. Chem. Rev. 219, 235–258 (2001).
[Crossref]

Bartoli, F. J.

J. S. Shirk, R. G. S. Pong, F. J. Bartoli, and A. W. Snow, “Optical limiter using a lead phthalocyanine,” Appl. Phys. Lett. 63(14), 1880–1882 (1993).
[Crossref]

J. S. Shirk, J. R. Lindle, F. J. Bartoli, Z. H. Kafafi, A. W. Snow, and M. E. Boyle, “Third-Order Nonlinear Optical Properties of Metallo-Phthalocyanines,” Int. J. Nonlinear Opt. Phys. 1(04), 699–726 (1992).
[Crossref]

J. S. Shirk, J. R. Lindle, F. J. Bartoli, C. A. Hoffman, Z. H. Kafafi, and A. W. Snow, “Off-Resonant 3rd-Order Optical Nonlinearities of Metal-Substituted Phthalocyanines,” Appl. Phys. Lett. 55(13), 1287–1288 (1989).
[Crossref]

Beck, A.

M. Hanack, D. Y. Meng, A. Beck, M. Sommerauer, and L. R. Subramanian, “Separation of structural isomers of tetra-tert-butylphthalocyaninatonickel(II),” J. Chem. Soc. Chem. Commun. 1993(1), 58–60 (1993).
[Crossref]

Bedworth, P. V.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

Boyle, M. E.

J. S. Shirk, J. R. Lindle, F. J. Bartoli, Z. H. Kafafi, A. W. Snow, and M. E. Boyle, “Third-Order Nonlinear Optical Properties of Metallo-Phthalocyanines,” Int. J. Nonlinear Opt. Phys. 1(04), 699–726 (1992).
[Crossref]

Brado, J. A.

A. R. Monahan, J. A. Brado, and A. F. Deluca, “Association of copper(II), vanadyl, and zinc(II) 4,4′,4″,4″-tetraalkylphthalocyanine dyes in benzene,” J. Phys. Chem. 76(14), 1994–1996 (1972).
[Crossref]

A. R. Monahan, A. F. Deluca, and J. A. Brado, “Dimerization of a copper(II)-phthalocyanine dye in carbon-tetrachloride and benzene,” J. Phys. Chem. 76(3), 446–449 (1972).
[Crossref]

Brant, M. C.

W. J. Su, T. M. Cooper, and M. C. Brant, “Investigation of reverse-saturable absorption in brominated porphyrins,” Chem. Mater. 10(5), 1212–1213 (1998).
[Crossref]

Calvete, M. J. F.

D. Dini, M. J. F. Calvete, M. Hanack, W. Z. Chen, and W. Ji, “Synthesis of axially substituted gallium, indium and thallium phthalocyanines with nonlinear optical properties,” ARKIVOC 2006(3), 77–96 (2005).
[Crossref]

Campillo, A. J.

B. L. Justus, A. L. Huston, and A. J. Campillo, “Broad-band thermal optical limiter,” Appl. Phys. Lett. 63(11), 1483–1485 (1993).
[Crossref]

Chen, C. T.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

Chen, W. Z.

D. Dini, M. J. F. Calvete, M. Hanack, W. Z. Chen, and W. Ji, “Synthesis of axially substituted gallium, indium and thallium phthalocyanines with nonlinear optical properties,” ARKIVOC 2006(3), 77–96 (2005).
[Crossref]

Choong, I.

J. W. Perry, K. Mansour, S. R. Marder, K. J. Perry, D. Alvarez, and I. Choong, “Enhanced Reverse Saturable Absorption and Optical Limiting in Heavy-Atom-Substituted Phthalocyanines,” Opt. Lett. 19(9), 625–627 (1994).
[Crossref] [PubMed]

K. Mansour, J. D. Alvarez, K. J. Perry, I. Choong, S. R. Marder, and J. W. Perry, “Dynamics of optical limiting in heavy-atom substituted phthalocyanines,” Proc. SPIE 1853, 132–141 (1993).
[Crossref]

Cooper, T. M.

W. J. Su, T. M. Cooper, and M. C. Brant, “Investigation of reverse-saturable absorption in brominated porphyrins,” Chem. Mater. 10(5), 1212–1213 (1998).
[Crossref]

Coulter, D. R.

T. H. Wei, D. J. Hagan, M. J. Sence, E. W. Vanstryland, J. W. Perry, and D. R. Coulter, “Direct measurements of nonlinear absorption and refraction in solutions of phthalocyanines,” App. Phys. B-Photophys, Laser Chem. 54, 46–51 (1992).

D. R. Coulter, V. M. Miskowski, J. W. Perry, T.-H. Wei, E. W. Van Stryland, and D. J. Hagan, “Optical Limiting In Solutions Of Metallo-Phthalocyanines And Naphthalocyanines,” Proc. SPIE 1105, 42–51 (1989).
[Crossref]

Cuellar, E. A.

E. A. Cuellar and T. J. Marks, “Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyanines,” Inorg. Chem. 20(11), 3766–3770 (1981).
[Crossref]

Deluca, A. F.

A. R. Monahan, J. A. Brado, and A. F. Deluca, “Association of copper(II), vanadyl, and zinc(II) 4,4′,4″,4″-tetraalkylphthalocyanine dyes in benzene,” J. Phys. Chem. 76(14), 1994–1996 (1972).
[Crossref]

A. R. Monahan, A. F. Deluca, and J. A. Brado, “Dimerization of a copper(II)-phthalocyanine dye in carbon-tetrachloride and benzene,” J. Phys. Chem. 76(3), 446–449 (1972).
[Crossref]

Dini, D.

D. Dini, M. J. F. Calvete, M. Hanack, W. Z. Chen, and W. Ji, “Synthesis of axially substituted gallium, indium and thallium phthalocyanines with nonlinear optical properties,” ARKIVOC 2006(3), 77–96 (2005).
[Crossref]

Dominguez, D. D.

D. D. Dominguez, A. W. Snow, J. S. Shirk, and R. G. S. Pong, “Polyethyleneoxide-capped phthalocyanines: limiting phthalocyanine aggregation to dimer formation,” J. Porphyr. Phthalocyanines 5(07), 582–592 (2001).
[Crossref]

Eyring, E. M.

Z. A. Schelly, D. J. Harward, P. Hemmes, and E. M. Eyring, “Bonding in dye aggregates - energetics of dimerization of aqueous cobalt(II)-4,4′,4″,4‴-tetrasulfophthalocyanine ion,” J. Phys. Chem. 74(16), 3040–3042 (1970).
[Crossref]

Fitzgerald, J. P.

P. D. Huffman, J. P. Fitzgerald, and J. S. Shirk, “New lead and thallium phthalocyanines as optical limiting materials,” Abstracts Am. Chem. Soc. 223, U238(2002).

Flom, S. R.

M. Hanack, T. Schneider, M. Barthel, J. S. Shirk, S. R. Flom, and R. G. S. Pong, “Indium phthalocyanines and naphthalocyanines for optical limiting,” Coord. Chem. Rev. 219, 235–258 (2001).
[Crossref]

J. S. Shirk, R. G. S. Pong, S. R. Flom, H. Heckmann, and M. Hanack, “Effect of axial substitution on the optical limiting properties of indium phthalocyanines,” J. Phys. Chem. A 104(7), 1438–1449 (2000).
[Crossref]

Garito, A. F.

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “3rd-Order Nonlinear Optical-Properties in Soluble Phthalocyanines with Tert-Butyl Substituents,” Jpn. J. Appl. Phys. 30(8), 1715–1719 (1991).
[Crossref]

George, R. D.

R. D. George, A. W. Snow, J. S. Shirk, and W. R. Barger, “The alpha substitution effect on phthalocyanine aggregation,” J. Porphyr. Phthalocyanines 2(01), 1–7 (1998).
[Crossref]

Hagan, D. J.

T. H. Wei, D. J. Hagan, M. J. Sence, E. W. Vanstryland, J. W. Perry, and D. R. Coulter, “Direct measurements of nonlinear absorption and refraction in solutions of phthalocyanines,” App. Phys. B-Photophys, Laser Chem. 54, 46–51 (1992).

M. J. Soileau, T. H. Wei, M. Sheikbahae, D. J. Hagan, M. Sence, and E. W. Vanstryland, “Nonlinear optical characterization of organic materials,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 207(1), 97–101 (1991).
[Crossref]

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. VanStryland, “Sensitive measurement of optical nonlinearities using a single beam,” IEEE J. Quantum Electron. 26(4), 760–769 (1990).
[Crossref]

D. R. Coulter, V. M. Miskowski, J. W. Perry, T.-H. Wei, E. W. Van Stryland, and D. J. Hagan, “Optical Limiting In Solutions Of Metallo-Phthalocyanines And Naphthalocyanines,” Proc. SPIE 1105, 42–51 (1989).
[Crossref]

Hall, T. W.

C. C. Leznoff and T. W. Hall, “The synthesis of a soluble, unsymmetrical phthalocyanine on a polymer support,” Tetrahedron Lett. 23(30), 3023–3026 (1982).
[Crossref]

Hanack, M.

D. Dini, M. J. F. Calvete, M. Hanack, W. Z. Chen, and W. Ji, “Synthesis of axially substituted gallium, indium and thallium phthalocyanines with nonlinear optical properties,” ARKIVOC 2006(3), 77–96 (2005).
[Crossref]

M. Hanack, T. Schneider, M. Barthel, J. S. Shirk, S. R. Flom, and R. G. S. Pong, “Indium phthalocyanines and naphthalocyanines for optical limiting,” Coord. Chem. Rev. 219, 235–258 (2001).
[Crossref]

J. S. Shirk, R. G. S. Pong, S. R. Flom, H. Heckmann, and M. Hanack, “Effect of axial substitution on the optical limiting properties of indium phthalocyanines,” J. Phys. Chem. A 104(7), 1438–1449 (2000).
[Crossref]

M. Hanack, D. Y. Meng, A. Beck, M. Sommerauer, and L. R. Subramanian, “Separation of structural isomers of tetra-tert-butylphthalocyaninatonickel(II),” J. Chem. Soc. Chem. Commun. 1993(1), 58–60 (1993).
[Crossref]

M. Hanack, J. Metz, and G. Pawlowski, “Soluble trans-di-1-alkynyl(tetraalkylphthalocyaninato)metal and poly-trans-ethynyl(tetraalkylphthalocyaninato)metal IVB Derivatives,” Chem. Ber. 115, 2836–2853 (1982).
[Crossref]

Harward, D. J.

Z. A. Schelly, D. J. Harward, P. Hemmes, and E. M. Eyring, “Bonding in dye aggregates - energetics of dimerization of aqueous cobalt(II)-4,4′,4″,4‴-tetrasulfophthalocyanine ion,” J. Phys. Chem. 74(16), 3040–3042 (1970).
[Crossref]

Heckmann, H.

J. S. Shirk, R. G. S. Pong, S. R. Flom, H. Heckmann, and M. Hanack, “Effect of axial substitution on the optical limiting properties of indium phthalocyanines,” J. Phys. Chem. A 104(7), 1438–1449 (2000).
[Crossref]

Hemmes, P.

Z. A. Schelly, D. J. Harward, P. Hemmes, and E. M. Eyring, “Bonding in dye aggregates - energetics of dimerization of aqueous cobalt(II)-4,4′,4″,4‴-tetrasulfophthalocyanine ion,” J. Phys. Chem. 74(16), 3040–3042 (1970).
[Crossref]

Hoffman, C. A.

J. S. Shirk, J. R. Lindle, F. J. Bartoli, C. A. Hoffman, Z. H. Kafafi, and A. W. Snow, “Off-Resonant 3rd-Order Optical Nonlinearities of Metal-Substituted Phthalocyanines,” Appl. Phys. Lett. 55(13), 1287–1288 (1989).
[Crossref]

Homborg, H.

K. Schweiger, H. Hueckstaedt, and H. Homborg, “Iodophthalocyaninato(2–)thallium(III) – Synthese und Kristallstruktur,” Z. Anorg. Allg. Chem. 624(2), 167–168 (1998).
[Crossref]

Hosoda, M.

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “3rd-Order Nonlinear Optical-Properties in Soluble Phthalocyanines with Tert-Butyl Substituents,” Jpn. J. Appl. Phys. 30(8), 1715–1719 (1991).
[Crossref]

Hueckstaedt, H.

K. Schweiger, H. Hueckstaedt, and H. Homborg, “Iodophthalocyaninato(2–)thallium(III) – Synthese und Kristallstruktur,” Z. Anorg. Allg. Chem. 624(2), 167–168 (1998).
[Crossref]

Huffman, P. D.

P. D. Huffman, J. P. Fitzgerald, and J. S. Shirk, “New lead and thallium phthalocyanines as optical limiting materials,” Abstracts Am. Chem. Soc. 223, U238(2002).

Huston, A. L.

B. L. Justus, A. L. Huston, and A. J. Campillo, “Broad-band thermal optical limiter,” Appl. Phys. Lett. 63(11), 1483–1485 (1993).
[Crossref]

Isoda, S.

T. Suga, S. Isoda, and T. Kobayashi, “Characterization and electrical conductivity of dithallium phthalocyanine (Tl2Pc),” J. Porphyr. Phthalocyanines 3(06), 397–405 (1999).
[Crossref]

Janczak, J.

J. Janczak and R. Kubiak, “Crystal and molecular-structure of dithallium phthalocyanine At 300-K,” J. Alloys Compd. 202(1-2), 69–72 (1993).
[Crossref]

Jarvis, N. L.

A. W. Snow and N. L. Jarvis, “Molecular association and monolayer formation of soluble phthalocyanine compounds,” J. Am. Chem. Soc. 106(17), 4706–4711 (1984).
[Crossref]

Ji, W.

D. Dini, M. J. F. Calvete, M. Hanack, W. Z. Chen, and W. Ji, “Synthesis of axially substituted gallium, indium and thallium phthalocyanines with nonlinear optical properties,” ARKIVOC 2006(3), 77–96 (2005).
[Crossref]

Justus, B. L.

B. L. Justus, A. L. Huston, and A. J. Campillo, “Broad-band thermal optical limiter,” Appl. Phys. Lett. 63(11), 1483–1485 (1993).
[Crossref]

Kafafi, Z. H.

J. S. Shirk, J. R. Lindle, F. J. Bartoli, Z. H. Kafafi, A. W. Snow, and M. E. Boyle, “Third-Order Nonlinear Optical Properties of Metallo-Phthalocyanines,” Int. J. Nonlinear Opt. Phys. 1(04), 699–726 (1992).
[Crossref]

J. S. Shirk, J. R. Lindle, F. J. Bartoli, C. A. Hoffman, Z. H. Kafafi, and A. W. Snow, “Off-Resonant 3rd-Order Optical Nonlinearities of Metal-Substituted Phthalocyanines,” Appl. Phys. Lett. 55(13), 1287–1288 (1989).
[Crossref]

Kobayashi, T.

T. Suga, S. Isoda, and T. Kobayashi, “Characterization and electrical conductivity of dithallium phthalocyanine (Tl2Pc),” J. Porphyr. Phthalocyanines 3(06), 397–405 (1999).
[Crossref]

Kubiak, R.

J. Janczak and R. Kubiak, “Crystal and molecular-structure of dithallium phthalocyanine At 300-K,” J. Alloys Compd. 202(1-2), 69–72 (1993).
[Crossref]

Lebedev, O. L.

S. A. Mikhalenko, S. V. Barkanova, O. L. Lebedev, and E. A. Lukyanets, “Phthalocyanines and related compounds IX. Synthesis and Electronic Absorption Spectra of tetra-4-t-butylphthalocyanines,” J. Gen. Chem. USSR 41, 2770–2773 (1971).

Lee, I. Y. S.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

Leznoff, C. C.

C. C. Leznoff and T. W. Hall, “The synthesis of a soluble, unsymmetrical phthalocyanine on a polymer support,” Tetrahedron Lett. 23(30), 3023–3026 (1982).
[Crossref]

Lindle, J. R.

J. S. Shirk, J. R. Lindle, F. J. Bartoli, Z. H. Kafafi, A. W. Snow, and M. E. Boyle, “Third-Order Nonlinear Optical Properties of Metallo-Phthalocyanines,” Int. J. Nonlinear Opt. Phys. 1(04), 699–726 (1992).
[Crossref]

J. S. Shirk, J. R. Lindle, F. J. Bartoli, C. A. Hoffman, Z. H. Kafafi, and A. W. Snow, “Off-Resonant 3rd-Order Optical Nonlinearities of Metal-Substituted Phthalocyanines,” Appl. Phys. Lett. 55(13), 1287–1288 (1989).
[Crossref]

Lukyanets, E. A.

S. A. Mikhalenko, S. V. Barkanova, O. L. Lebedev, and E. A. Lukyanets, “Phthalocyanines and related compounds IX. Synthesis and Electronic Absorption Spectra of tetra-4-t-butylphthalocyanines,” J. Gen. Chem. USSR 41, 2770–2773 (1971).

Mansour, K.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

J. W. Perry, K. Mansour, S. R. Marder, K. J. Perry, D. Alvarez, and I. Choong, “Enhanced Reverse Saturable Absorption and Optical Limiting in Heavy-Atom-Substituted Phthalocyanines,” Opt. Lett. 19(9), 625–627 (1994).
[Crossref] [PubMed]

K. Mansour, J. D. Alvarez, K. J. Perry, I. Choong, S. R. Marder, and J. W. Perry, “Dynamics of optical limiting in heavy-atom substituted phthalocyanines,” Proc. SPIE 1853, 132–141 (1993).
[Crossref]

Marder, S. R.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

J. W. Perry, K. Mansour, S. R. Marder, K. J. Perry, D. Alvarez, and I. Choong, “Enhanced Reverse Saturable Absorption and Optical Limiting in Heavy-Atom-Substituted Phthalocyanines,” Opt. Lett. 19(9), 625–627 (1994).
[Crossref] [PubMed]

K. Mansour, J. D. Alvarez, K. J. Perry, I. Choong, S. R. Marder, and J. W. Perry, “Dynamics of optical limiting in heavy-atom substituted phthalocyanines,” Proc. SPIE 1853, 132–141 (1993).
[Crossref]

Marks, T. J.

E. A. Cuellar and T. J. Marks, “Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyanines,” Inorg. Chem. 20(11), 3766–3770 (1981).
[Crossref]

Meng, D. Y.

M. Hanack, D. Y. Meng, A. Beck, M. Sommerauer, and L. R. Subramanian, “Separation of structural isomers of tetra-tert-butylphthalocyaninatonickel(II),” J. Chem. Soc. Chem. Commun. 1993(1), 58–60 (1993).
[Crossref]

Metz, J.

M. Hanack, J. Metz, and G. Pawlowski, “Soluble trans-di-1-alkynyl(tetraalkylphthalocyaninato)metal and poly-trans-ethynyl(tetraalkylphthalocyaninato)metal IVB Derivatives,” Chem. Ber. 115, 2836–2853 (1982).
[Crossref]

Mikhalenko, S. A.

S. A. Mikhalenko, S. V. Barkanova, O. L. Lebedev, and E. A. Lukyanets, “Phthalocyanines and related compounds IX. Synthesis and Electronic Absorption Spectra of tetra-4-t-butylphthalocyanines,” J. Gen. Chem. USSR 41, 2770–2773 (1971).

Miles, P.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

Miskowski, V. M.

D. R. Coulter, V. M. Miskowski, J. W. Perry, T.-H. Wei, E. W. Van Stryland, and D. J. Hagan, “Optical Limiting In Solutions Of Metallo-Phthalocyanines And Naphthalocyanines,” Proc. SPIE 1105, 42–51 (1989).
[Crossref]

Monahan, A. R.

A. R. Monahan, J. A. Brado, and A. F. Deluca, “Association of copper(II), vanadyl, and zinc(II) 4,4′,4″,4″-tetraalkylphthalocyanine dyes in benzene,” J. Phys. Chem. 76(14), 1994–1996 (1972).
[Crossref]

A. R. Monahan, A. F. Deluca, and J. A. Brado, “Dimerization of a copper(II)-phthalocyanine dye in carbon-tetrachloride and benzene,” J. Phys. Chem. 76(3), 446–449 (1972).
[Crossref]

Ng, D.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

Parr, R. G.

P. W. Ayers, R. G. Parr, and R. G. Pearson, “Elucidating the hard/soft acid/base principle: A perspective based on half-reactions,” J. Chem. Phys. 124(19), 194107 (2006).
[Crossref] [PubMed]

Pawlowski, G.

M. Hanack, J. Metz, and G. Pawlowski, “Soluble trans-di-1-alkynyl(tetraalkylphthalocyaninato)metal and poly-trans-ethynyl(tetraalkylphthalocyaninato)metal IVB Derivatives,” Chem. Ber. 115, 2836–2853 (1982).
[Crossref]

Pearson, R. G.

P. W. Ayers, R. G. Parr, and R. G. Pearson, “Elucidating the hard/soft acid/base principle: A perspective based on half-reactions,” J. Chem. Phys. 124(19), 194107 (2006).
[Crossref] [PubMed]

R. G. Pearson, “Hard and soft acids and bases,” J. Am. Chem. Soc. 85(22), 3533–3539 (1963).
[Crossref]

Perry, J. W.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

J. W. Perry, K. Mansour, S. R. Marder, K. J. Perry, D. Alvarez, and I. Choong, “Enhanced Reverse Saturable Absorption and Optical Limiting in Heavy-Atom-Substituted Phthalocyanines,” Opt. Lett. 19(9), 625–627 (1994).
[Crossref] [PubMed]

K. Mansour, J. D. Alvarez, K. J. Perry, I. Choong, S. R. Marder, and J. W. Perry, “Dynamics of optical limiting in heavy-atom substituted phthalocyanines,” Proc. SPIE 1853, 132–141 (1993).
[Crossref]

T. H. Wei, D. J. Hagan, M. J. Sence, E. W. Vanstryland, J. W. Perry, and D. R. Coulter, “Direct measurements of nonlinear absorption and refraction in solutions of phthalocyanines,” App. Phys. B-Photophys, Laser Chem. 54, 46–51 (1992).

D. R. Coulter, V. M. Miskowski, J. W. Perry, T.-H. Wei, E. W. Van Stryland, and D. J. Hagan, “Optical Limiting In Solutions Of Metallo-Phthalocyanines And Naphthalocyanines,” Proc. SPIE 1105, 42–51 (1989).
[Crossref]

Perry, K. J.

J. W. Perry, K. Mansour, S. R. Marder, K. J. Perry, D. Alvarez, and I. Choong, “Enhanced Reverse Saturable Absorption and Optical Limiting in Heavy-Atom-Substituted Phthalocyanines,” Opt. Lett. 19(9), 625–627 (1994).
[Crossref] [PubMed]

K. Mansour, J. D. Alvarez, K. J. Perry, I. Choong, S. R. Marder, and J. W. Perry, “Dynamics of optical limiting in heavy-atom substituted phthalocyanines,” Proc. SPIE 1853, 132–141 (1993).
[Crossref]

Pong, R. G. S.

M. Hanack, T. Schneider, M. Barthel, J. S. Shirk, S. R. Flom, and R. G. S. Pong, “Indium phthalocyanines and naphthalocyanines for optical limiting,” Coord. Chem. Rev. 219, 235–258 (2001).
[Crossref]

D. D. Dominguez, A. W. Snow, J. S. Shirk, and R. G. S. Pong, “Polyethyleneoxide-capped phthalocyanines: limiting phthalocyanine aggregation to dimer formation,” J. Porphyr. Phthalocyanines 5(07), 582–592 (2001).
[Crossref]

J. S. Shirk, R. G. S. Pong, S. R. Flom, H. Heckmann, and M. Hanack, “Effect of axial substitution on the optical limiting properties of indium phthalocyanines,” J. Phys. Chem. A 104(7), 1438–1449 (2000).
[Crossref]

J. S. Shirk, R. G. S. Pong, F. J. Bartoli, and A. W. Snow, “Optical limiter using a lead phthalocyanine,” Appl. Phys. Lett. 63(14), 1880–1882 (1993).
[Crossref]

Said, A. A.

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. VanStryland, “Sensitive measurement of optical nonlinearities using a single beam,” IEEE J. Quantum Electron. 26(4), 760–769 (1990).
[Crossref]

Sasabe, H.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “3rd-Order Nonlinear Optical-Properties in Soluble Phthalocyanines with Tert-Butyl Substituents,” Jpn. J. Appl. Phys. 30(8), 1715–1719 (1991).
[Crossref]

Schelly, Z. A.

Z. A. Schelly, D. J. Harward, P. Hemmes, and E. M. Eyring, “Bonding in dye aggregates - energetics of dimerization of aqueous cobalt(II)-4,4′,4″,4‴-tetrasulfophthalocyanine ion,” J. Phys. Chem. 74(16), 3040–3042 (1970).
[Crossref]

Schneider, T.

M. Hanack, T. Schneider, M. Barthel, J. S. Shirk, S. R. Flom, and R. G. S. Pong, “Indium phthalocyanines and naphthalocyanines for optical limiting,” Coord. Chem. Rev. 219, 235–258 (2001).
[Crossref]

Schweiger, K.

K. Schweiger, H. Hueckstaedt, and H. Homborg, “Iodophthalocyaninato(2–)thallium(III) – Synthese und Kristallstruktur,” Z. Anorg. Allg. Chem. 624(2), 167–168 (1998).
[Crossref]

Sence, M.

M. J. Soileau, T. H. Wei, M. Sheikbahae, D. J. Hagan, M. Sence, and E. W. Vanstryland, “Nonlinear optical characterization of organic materials,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 207(1), 97–101 (1991).
[Crossref]

Sence, M. J.

T. H. Wei, D. J. Hagan, M. J. Sence, E. W. Vanstryland, J. W. Perry, and D. R. Coulter, “Direct measurements of nonlinear absorption and refraction in solutions of phthalocyanines,” App. Phys. B-Photophys, Laser Chem. 54, 46–51 (1992).

Sheikbahae, M.

M. J. Soileau, T. H. Wei, M. Sheikbahae, D. J. Hagan, M. Sence, and E. W. Vanstryland, “Nonlinear optical characterization of organic materials,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 207(1), 97–101 (1991).
[Crossref]

Sheik-Bahae, M.

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. VanStryland, “Sensitive measurement of optical nonlinearities using a single beam,” IEEE J. Quantum Electron. 26(4), 760–769 (1990).
[Crossref]

Shirk, J. S.

P. D. Huffman, J. P. Fitzgerald, and J. S. Shirk, “New lead and thallium phthalocyanines as optical limiting materials,” Abstracts Am. Chem. Soc. 223, U238(2002).

M. Hanack, T. Schneider, M. Barthel, J. S. Shirk, S. R. Flom, and R. G. S. Pong, “Indium phthalocyanines and naphthalocyanines for optical limiting,” Coord. Chem. Rev. 219, 235–258 (2001).
[Crossref]

D. D. Dominguez, A. W. Snow, J. S. Shirk, and R. G. S. Pong, “Polyethyleneoxide-capped phthalocyanines: limiting phthalocyanine aggregation to dimer formation,” J. Porphyr. Phthalocyanines 5(07), 582–592 (2001).
[Crossref]

J. S. Shirk, R. G. S. Pong, S. R. Flom, H. Heckmann, and M. Hanack, “Effect of axial substitution on the optical limiting properties of indium phthalocyanines,” J. Phys. Chem. A 104(7), 1438–1449 (2000).
[Crossref]

J. S. Shirk, “Protecting the Warfighter's Vision In a Laser-rich, Battlefield Environment,” Optics and Photonics News 11(4), 19–23 (2000).
[Crossref]

R. D. George, A. W. Snow, J. S. Shirk, and W. R. Barger, “The alpha substitution effect on phthalocyanine aggregation,” J. Porphyr. Phthalocyanines 2(01), 1–7 (1998).
[Crossref]

J. S. Shirk, R. G. S. Pong, F. J. Bartoli, and A. W. Snow, “Optical limiter using a lead phthalocyanine,” Appl. Phys. Lett. 63(14), 1880–1882 (1993).
[Crossref]

J. S. Shirk, J. R. Lindle, F. J. Bartoli, Z. H. Kafafi, A. W. Snow, and M. E. Boyle, “Third-Order Nonlinear Optical Properties of Metallo-Phthalocyanines,” Int. J. Nonlinear Opt. Phys. 1(04), 699–726 (1992).
[Crossref]

J. S. Shirk, J. R. Lindle, F. J. Bartoli, C. A. Hoffman, Z. H. Kafafi, and A. W. Snow, “Off-Resonant 3rd-Order Optical Nonlinearities of Metal-Substituted Phthalocyanines,” Appl. Phys. Lett. 55(13), 1287–1288 (1989).
[Crossref]

Snow, A. W.

D. D. Dominguez, A. W. Snow, J. S. Shirk, and R. G. S. Pong, “Polyethyleneoxide-capped phthalocyanines: limiting phthalocyanine aggregation to dimer formation,” J. Porphyr. Phthalocyanines 5(07), 582–592 (2001).
[Crossref]

R. D. George, A. W. Snow, J. S. Shirk, and W. R. Barger, “The alpha substitution effect on phthalocyanine aggregation,” J. Porphyr. Phthalocyanines 2(01), 1–7 (1998).
[Crossref]

J. S. Shirk, R. G. S. Pong, F. J. Bartoli, and A. W. Snow, “Optical limiter using a lead phthalocyanine,” Appl. Phys. Lett. 63(14), 1880–1882 (1993).
[Crossref]

J. S. Shirk, J. R. Lindle, F. J. Bartoli, Z. H. Kafafi, A. W. Snow, and M. E. Boyle, “Third-Order Nonlinear Optical Properties of Metallo-Phthalocyanines,” Int. J. Nonlinear Opt. Phys. 1(04), 699–726 (1992).
[Crossref]

J. S. Shirk, J. R. Lindle, F. J. Bartoli, C. A. Hoffman, Z. H. Kafafi, and A. W. Snow, “Off-Resonant 3rd-Order Optical Nonlinearities of Metal-Substituted Phthalocyanines,” Appl. Phys. Lett. 55(13), 1287–1288 (1989).
[Crossref]

A. W. Snow and N. L. Jarvis, “Molecular association and monolayer formation of soluble phthalocyanine compounds,” J. Am. Chem. Soc. 106(17), 4706–4711 (1984).
[Crossref]

Soileau, M. J.

M. J. Soileau, T. H. Wei, M. Sheikbahae, D. J. Hagan, M. Sence, and E. W. Vanstryland, “Nonlinear optical characterization of organic materials,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 207(1), 97–101 (1991).
[Crossref]

Sommerauer, M.

M. Hanack, D. Y. Meng, A. Beck, M. Sommerauer, and L. R. Subramanian, “Separation of structural isomers of tetra-tert-butylphthalocyaninatonickel(II),” J. Chem. Soc. Chem. Commun. 1993(1), 58–60 (1993).
[Crossref]

Su, W. J.

W. J. Su, T. M. Cooper, and M. C. Brant, “Investigation of reverse-saturable absorption in brominated porphyrins,” Chem. Mater. 10(5), 1212–1213 (1998).
[Crossref]

Subramanian, L. R.

M. Hanack, D. Y. Meng, A. Beck, M. Sommerauer, and L. R. Subramanian, “Separation of structural isomers of tetra-tert-butylphthalocyaninatonickel(II),” J. Chem. Soc. Chem. Commun. 1993(1), 58–60 (1993).
[Crossref]

Suga, T.

T. Suga, S. Isoda, and T. Kobayashi, “Characterization and electrical conductivity of dithallium phthalocyanine (Tl2Pc),” J. Porphyr. Phthalocyanines 3(06), 397–405 (1999).
[Crossref]

Tian, M.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

Van Stryland, E. W.

D. R. Coulter, V. M. Miskowski, J. W. Perry, T.-H. Wei, E. W. Van Stryland, and D. J. Hagan, “Optical Limiting In Solutions Of Metallo-Phthalocyanines And Naphthalocyanines,” Proc. SPIE 1105, 42–51 (1989).
[Crossref]

Vanstryland, E. W.

T. H. Wei, D. J. Hagan, M. J. Sence, E. W. Vanstryland, J. W. Perry, and D. R. Coulter, “Direct measurements of nonlinear absorption and refraction in solutions of phthalocyanines,” App. Phys. B-Photophys, Laser Chem. 54, 46–51 (1992).

M. J. Soileau, T. H. Wei, M. Sheikbahae, D. J. Hagan, M. Sence, and E. W. Vanstryland, “Nonlinear optical characterization of organic materials,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 207(1), 97–101 (1991).
[Crossref]

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. VanStryland, “Sensitive measurement of optical nonlinearities using a single beam,” IEEE J. Quantum Electron. 26(4), 760–769 (1990).
[Crossref]

Wada, T.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “3rd-Order Nonlinear Optical-Properties in Soluble Phthalocyanines with Tert-Butyl Substituents,” Jpn. J. Appl. Phys. 30(8), 1715–1719 (1991).
[Crossref]

Wei, T. H.

T. H. Wei, D. J. Hagan, M. J. Sence, E. W. Vanstryland, J. W. Perry, and D. R. Coulter, “Direct measurements of nonlinear absorption and refraction in solutions of phthalocyanines,” App. Phys. B-Photophys, Laser Chem. 54, 46–51 (1992).

M. J. Soileau, T. H. Wei, M. Sheikbahae, D. J. Hagan, M. Sence, and E. W. Vanstryland, “Nonlinear optical characterization of organic materials,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 207(1), 97–101 (1991).
[Crossref]

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. VanStryland, “Sensitive measurement of optical nonlinearities using a single beam,” IEEE J. Quantum Electron. 26(4), 760–769 (1990).
[Crossref]

Wei, T.-H.

D. R. Coulter, V. M. Miskowski, J. W. Perry, T.-H. Wei, E. W. Van Stryland, and D. J. Hagan, “Optical Limiting In Solutions Of Metallo-Phthalocyanines And Naphthalocyanines,” Proc. SPIE 1105, 42–51 (1989).
[Crossref]

Wu, X. L.

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

Yamada, A.

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “3rd-Order Nonlinear Optical-Properties in Soluble Phthalocyanines with Tert-Butyl Substituents,” Jpn. J. Appl. Phys. 30(8), 1715–1719 (1991).
[Crossref]

Abstracts Am. Chem. Soc. (1)

P. D. Huffman, J. P. Fitzgerald, and J. S. Shirk, “New lead and thallium phthalocyanines as optical limiting materials,” Abstracts Am. Chem. Soc. 223, U238(2002).

App. Phys. B-Photophys, Laser Chem. (1)

T. H. Wei, D. J. Hagan, M. J. Sence, E. W. Vanstryland, J. W. Perry, and D. R. Coulter, “Direct measurements of nonlinear absorption and refraction in solutions of phthalocyanines,” App. Phys. B-Photophys, Laser Chem. 54, 46–51 (1992).

Appl. Phys. Lett. (3)

J. S. Shirk, J. R. Lindle, F. J. Bartoli, C. A. Hoffman, Z. H. Kafafi, and A. W. Snow, “Off-Resonant 3rd-Order Optical Nonlinearities of Metal-Substituted Phthalocyanines,” Appl. Phys. Lett. 55(13), 1287–1288 (1989).
[Crossref]

J. S. Shirk, R. G. S. Pong, F. J. Bartoli, and A. W. Snow, “Optical limiter using a lead phthalocyanine,” Appl. Phys. Lett. 63(14), 1880–1882 (1993).
[Crossref]

B. L. Justus, A. L. Huston, and A. J. Campillo, “Broad-band thermal optical limiter,” Appl. Phys. Lett. 63(11), 1483–1485 (1993).
[Crossref]

ARKIVOC (1)

D. Dini, M. J. F. Calvete, M. Hanack, W. Z. Chen, and W. Ji, “Synthesis of axially substituted gallium, indium and thallium phthalocyanines with nonlinear optical properties,” ARKIVOC 2006(3), 77–96 (2005).
[Crossref]

Chem. Ber. (1)

M. Hanack, J. Metz, and G. Pawlowski, “Soluble trans-di-1-alkynyl(tetraalkylphthalocyaninato)metal and poly-trans-ethynyl(tetraalkylphthalocyaninato)metal IVB Derivatives,” Chem. Ber. 115, 2836–2853 (1982).
[Crossref]

Chem. Mater. (1)

W. J. Su, T. M. Cooper, and M. C. Brant, “Investigation of reverse-saturable absorption in brominated porphyrins,” Chem. Mater. 10(5), 1212–1213 (1998).
[Crossref]

Coord. Chem. Rev. (1)

M. Hanack, T. Schneider, M. Barthel, J. S. Shirk, S. R. Flom, and R. G. S. Pong, “Indium phthalocyanines and naphthalocyanines for optical limiting,” Coord. Chem. Rev. 219, 235–258 (2001).
[Crossref]

IEEE J. Quantum Electron. (1)

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. VanStryland, “Sensitive measurement of optical nonlinearities using a single beam,” IEEE J. Quantum Electron. 26(4), 760–769 (1990).
[Crossref]

Inorg. Chem. (1)

E. A. Cuellar and T. J. Marks, “Synthesis and characterization of metallo and metal-free octaalkylphthalocyanines and uranyl decaalkylsuperphthalocyanines,” Inorg. Chem. 20(11), 3766–3770 (1981).
[Crossref]

Int. J. Nonlinear Opt. Phys. (1)

J. S. Shirk, J. R. Lindle, F. J. Bartoli, Z. H. Kafafi, A. W. Snow, and M. E. Boyle, “Third-Order Nonlinear Optical Properties of Metallo-Phthalocyanines,” Int. J. Nonlinear Opt. Phys. 1(04), 699–726 (1992).
[Crossref]

J. Alloys Compd. (1)

J. Janczak and R. Kubiak, “Crystal and molecular-structure of dithallium phthalocyanine At 300-K,” J. Alloys Compd. 202(1-2), 69–72 (1993).
[Crossref]

J. Am. Chem. Soc. (2)

R. G. Pearson, “Hard and soft acids and bases,” J. Am. Chem. Soc. 85(22), 3533–3539 (1963).
[Crossref]

A. W. Snow and N. L. Jarvis, “Molecular association and monolayer formation of soluble phthalocyanine compounds,” J. Am. Chem. Soc. 106(17), 4706–4711 (1984).
[Crossref]

J. Chem. Phys. (1)

P. W. Ayers, R. G. Parr, and R. G. Pearson, “Elucidating the hard/soft acid/base principle: A perspective based on half-reactions,” J. Chem. Phys. 124(19), 194107 (2006).
[Crossref] [PubMed]

J. Chem. Soc. Chem. Commun. (1)

M. Hanack, D. Y. Meng, A. Beck, M. Sommerauer, and L. R. Subramanian, “Separation of structural isomers of tetra-tert-butylphthalocyaninatonickel(II),” J. Chem. Soc. Chem. Commun. 1993(1), 58–60 (1993).
[Crossref]

J. Gen. Chem. USSR (1)

S. A. Mikhalenko, S. V. Barkanova, O. L. Lebedev, and E. A. Lukyanets, “Phthalocyanines and related compounds IX. Synthesis and Electronic Absorption Spectra of tetra-4-t-butylphthalocyanines,” J. Gen. Chem. USSR 41, 2770–2773 (1971).

J. Phys. Chem. (3)

Z. A. Schelly, D. J. Harward, P. Hemmes, and E. M. Eyring, “Bonding in dye aggregates - energetics of dimerization of aqueous cobalt(II)-4,4′,4″,4‴-tetrasulfophthalocyanine ion,” J. Phys. Chem. 74(16), 3040–3042 (1970).
[Crossref]

A. R. Monahan, J. A. Brado, and A. F. Deluca, “Association of copper(II), vanadyl, and zinc(II) 4,4′,4″,4″-tetraalkylphthalocyanine dyes in benzene,” J. Phys. Chem. 76(14), 1994–1996 (1972).
[Crossref]

A. R. Monahan, A. F. Deluca, and J. A. Brado, “Dimerization of a copper(II)-phthalocyanine dye in carbon-tetrachloride and benzene,” J. Phys. Chem. 76(3), 446–449 (1972).
[Crossref]

J. Phys. Chem. A (1)

J. S. Shirk, R. G. S. Pong, S. R. Flom, H. Heckmann, and M. Hanack, “Effect of axial substitution on the optical limiting properties of indium phthalocyanines,” J. Phys. Chem. A 104(7), 1438–1449 (2000).
[Crossref]

J. Porphyr. Phthalocyanines (3)

R. D. George, A. W. Snow, J. S. Shirk, and W. R. Barger, “The alpha substitution effect on phthalocyanine aggregation,” J. Porphyr. Phthalocyanines 2(01), 1–7 (1998).
[Crossref]

D. D. Dominguez, A. W. Snow, J. S. Shirk, and R. G. S. Pong, “Polyethyleneoxide-capped phthalocyanines: limiting phthalocyanine aggregation to dimer formation,” J. Porphyr. Phthalocyanines 5(07), 582–592 (2001).
[Crossref]

T. Suga, S. Isoda, and T. Kobayashi, “Characterization and electrical conductivity of dithallium phthalocyanine (Tl2Pc),” J. Porphyr. Phthalocyanines 3(06), 397–405 (1999).
[Crossref]

Jpn. J. Appl. Phys. (1)

M. Hosoda, T. Wada, A. Yamada, A. F. Garito, and H. Sasabe, “3rd-Order Nonlinear Optical-Properties in Soluble Phthalocyanines with Tert-Butyl Substituents,” Jpn. J. Appl. Phys. 30(8), 1715–1719 (1991).
[Crossref]

Mol. Cryst. Liq. Cryst. (Phila. Pa.) (1)

M. J. Soileau, T. H. Wei, M. Sheikbahae, D. J. Hagan, M. Sence, and E. W. Vanstryland, “Nonlinear optical characterization of organic materials,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 207(1), 97–101 (1991).
[Crossref]

Opt. Lett. (1)

Optics and Photonics News (1)

J. S. Shirk, “Protecting the Warfighter's Vision In a Laser-rich, Battlefield Environment,” Optics and Photonics News 11(4), 19–23 (2000).
[Crossref]

Proc. SPIE (2)

D. R. Coulter, V. M. Miskowski, J. W. Perry, T.-H. Wei, E. W. Van Stryland, and D. J. Hagan, “Optical Limiting In Solutions Of Metallo-Phthalocyanines And Naphthalocyanines,” Proc. SPIE 1105, 42–51 (1989).
[Crossref]

K. Mansour, J. D. Alvarez, K. J. Perry, I. Choong, S. R. Marder, and J. W. Perry, “Dynamics of optical limiting in heavy-atom substituted phthalocyanines,” Proc. SPIE 1853, 132–141 (1993).
[Crossref]

Science (1)

J. W. Perry, K. Mansour, I. Y. S. Lee, X. L. Wu, P. V. Bedworth, C. T. Chen, D. Ng, S. R. Marder, P. Miles, T. Wada, M. Tian, and H. Sasabe, “Organic optical limiter with a strong nonlinear absorptive response,” Science 273(5281), 1533–1536 (1996).
[Crossref]

Tetrahedron Lett. (1)

C. C. Leznoff and T. W. Hall, “The synthesis of a soluble, unsymmetrical phthalocyanine on a polymer support,” Tetrahedron Lett. 23(30), 3023–3026 (1982).
[Crossref]

Z. Anorg. Allg. Chem. (1)

K. Schweiger, H. Hueckstaedt, and H. Homborg, “Iodophthalocyaninato(2–)thallium(III) – Synthese und Kristallstruktur,” Z. Anorg. Allg. Chem. 624(2), 167–168 (1998).
[Crossref]

Other (4)

J. S. Shirk, R. G. S. Pong, S. R. Flom, M. E. Boyle, and A. W. Snow, “Materials for reverse saturable absorption optical limiters,” in Materials for Optical Limiting R. Crane, K. Lewis, E. VanStryland, and M. Khoshnevisan, eds. (Mater. Res. Soc.Symp. Proc. 374, Pittsburgh, PA, 1995), pp. 201–209.

J. S. Shirk, J. R. Lindle, S. R. Flom, F. J. Bartoli, and A. W. Snow, “3rd-Order Nonlinear Optical-Properties of Phthalocyanines,” in Electrical, Optical, and Magnetic Properties of Organic Solid State Materials, L. Y. Chiang, A. F. Garito, and D. J. Sandman, eds. (Mater. Res. Soc.Symp. Proc. 247, Pittsburgh, PA, 1992), pp. 197–201.

G. Schmid, M. Sommerauer, M. Geyer, and M. Hanack, “Synthesis and Chromatographic Separation of Tetrasubstituted and Unsymmetrically Substituted Phthalocyanines ” in Phthalocyanines: Properties and Applications,4, C. C. Leznoff, and A. P. B. Lever, eds. (VCH, New York, 1996), pp. 1–18.

J. W. Buchler and D. K. P. Ng, “Metal Tetrapyrole Double- and Triple-Deckers with Special Emphasis on Porphyrin Systems,” in Phorphyrin Handbook,3, K. M. Kadish, K. M. Smith, and R. Guilard, eds. (Academic Press, San Diego, CA, 2000), pp. 245–294.

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Figures (16)

Fig. 1
Fig. 1 Synthesis of Tl2(t-Bu4Pc), 1, and oxidation to Tl(t-Bu4Pc)X, 2-4.
Fig. 2
Fig. 2 Changes in visible spectrum for conversion of 1 to 4 upon titration with iodine. The spectrum drawn in blue and marked with the down arrows is that of 1, while the spectrum drawn in red and marked with the up arrows is that of the product, 4. Note the three isosbestic points at 446, 528 and 716 nm.
Fig. 3
Fig. 3 Expanded regions of the 1H NMR spectrum of 4 recorded in CDCl3.
Fig. 4
Fig. 4 Phthalocyanine chemical structure showing [21] the differing possible substitutions on the peripheral β carbon atoms.
Fig. 5
Fig. 5 One possible isomeric form of 2-4 and its representation.
Fig. 6
Fig. 6 Visible spectrum of 4 at several concentrations in chloroform.
Fig. 7
Fig. 7 Molar extinction coefficients of 4 at several concentrations in toluene.
Fig. 8
Fig. 8 Transient white light absorption apparatus.
Fig. 9
Fig. 9 Transient absorbance of 4 in toluene (1.06 mM) at several relatively long delays following excitation at 633 nm.
Fig. 10
Fig. 10 Transient absorbance of 4 in toluene (0.93 mM) at several relatively short delays. The spectra show the effects of a wavelength chirp in the white light probe pulse.
Fig. 11
Fig. 11 Chirp compensated time evolution of ΔOD signal of 4 in toluene at several wavelengths.
Fig. 12
Fig. 12 Early time response after subtraction of a constant long-time response and normalization to the peak response.
Fig. 13
Fig. 13 Spectral dependence of the amplitudes of a three exponential fit to the transient absorption data.
Fig. 14
Fig. 14 Open aperture Z-scan response of 4.
Fig. 15
Fig. 15 Closed-aperture (40%) Z-scan ratioed to the open aperture response of 4.
Fig. 16
Fig. 16 Optical limiting response of 4 at 532 nm in an f/5 optical limiter system.

Tables (1)

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Table 1 Phthalocyanine stereoisomers structures, symmetry groups, substituent environments and statistical populations.

Equations (1)

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  T l 2 ( t B u 4 P c )   +   X 2   à   T l ( t B u 4 P c ) X   +   T l ( I ) X

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