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Soluble axially substituted phthalocyanines: Synthesis and nonlinear optical response

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Abstract

This review lays special stress on describing the synthesis of soluble axially substituted or bridged indium, gallium and titanium phthalocyanine complexes and their electronic absorption characteristics, photophysical and nonlinear optical properties. The enhanced solubility of the axially substituted or bridged phthalocyanine monomers and dimers, compared to the chloro analogues, shows that the usual tendency of phthalocyanines to form aggregates can be effectively suppressed by axial substitution. Axial substitution in phthalocyanine complexes has provoked relevant changes on the electronic structure of the molecule by altering the π-electronic distribution due to the dipole moment of the central metal-axial ligand bond. The nanosecond nonlinear absorption and the optical limiting of indium, gallium and titanium phthalocyanines seem to be dominated by a strong triplet state absorption in the optical region comprised between the Q- and B-bands in their UV/Vis absorption spectra.

Graphical Abstract

A series of highly soluble axially substituted and bridged phthalocyanine and naphthalocyanine complexes have been synthesized. Axial substitution in phthalocyanine complexes has provoked relevant changes on the electronic structure of the molecule by altering the π-electronic distribution due to the dipole moment of the central metal-axial ligand bond.

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References

  1. J. ZYSS, in “Nonlinear Optics: Materials, Physics and Devices” (Academic Press, Boston, 1993).

    Google Scholar 

  2. H. S. NALWA and S. MIYATA, “Nonlinear optics of organic molecules and polymers” (CRC Press, Boca Raton, FL, 1997).

    Book  Google Scholar 

  3. N. B. MCKEOWN, in “Phthalocyanine Materials: Synthesis, Structure and Function,” edited by B. Dunn, J. W. Goodby and A. R. West (Cambridge University Press, 1998).

  4. H. S. NALWA and J. S. SHIRK, in “Phthalocyanines: Properties and Applications,” edited by C. C. Leznoff and A. B. P. Lever (VCH Publishers, Inc., New York, 1996) Vol. 4, p. 79.

  5. M. J. STILLMAN and T. NYOKONG, in “Phthalocyanines: Properties and Applications,” edited by C. C. Leznoff and A. B. P. Lever (VCH Publishers, Inc., New York, 1989) Vol. 1, p. 133.

    Google Scholar 

  6. B. F. LEVINE and C. G. BETHEA, Appl. Phys. Lett. 24 (1974) 445.

    Article  CAS  Google Scholar 

  7. (a) E. W. VAN STRYLAND, M. SHEIK-BAHAE, A. A. SAID and D. J. HAGAN, Prog. Cryst. Growth Charact. 27 (1993) 279; M. SHEIK-BAHAE, A. A. SAID, T. H. WEI and E. W. VAN STRYLAND, IEEE J. Quant. Electr. QE-26 (1990) 760.

  8. (a) F. KAJZAR, J. MESSIER and C. ROSILIO, J. Appl. Phys. 60 (1986) 3040; (b) G. R. MEREDITH, B. BUCHALTER and C. HANZLIK, J. Chem. Phys. 78 (1983) 1533.

  9. J. F. REINTJES, in “Nonlinear Optical Parametric Processes in Liquids and Gases“ (Academic Press, New York, 1984) p. 327; R. C. LIND, D. G. STEEL and G. J. DUNNING, Opt. Eng. 21 (1982) 190; (c) A. YARIV, IEEE J. Quant. Electr. QE-14 (1978) 650.

    Book  Google Scholar 

  10. A. W. SNOW, J. S. SHIRK and L. H. PEEBLES Jr., in Proceedings of the International Conference on Porphyrins and Phthalocyanines-Symposium Lectures, DiJon, France, June 25–30, 2000, p. 177.

  11. J. S. SHIRK, R. G. S. PONG, S. R. FLOM, H. HECKMANN and M. HANACK, J. Phys. Chem. A 104 (2000) 1438.

    Article  CAS  Google Scholar 

  12. M. HANACK, T. SCHNEIDER, M. BARTHEL, J. S. SHIRK, S. R. FLOM and R. G. S. PONG, Coord. Chem. Rev. 219/221 (2001) 235.

    Article  Google Scholar 

  13. 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, Science 273 (1996) 1533.

    Article  CAS  Google Scholar 

  14. Y. CHEN, M. FUJITSUKA, S. M. O’FLAHERTY, M. HANACK, O. ITO and W. J. BLAU, Adv. Mater. 15 (2003) 899.

    Article  CAS  Google Scholar 

  15. (a) Y. CHEN, S. O’FLAHERTY, M. FUJITSUKA, M. HANACK, L. R. SUBRAMANIAN, O. ITO and W. J. BLAU, Chem. Mater. 14 (2002) 5163; S. M. O’FLAHERTY, S. V. HOLD, Y. CHEN, M. HANACK and W. J. BLAU, in Proceedings of SPIE- Organic Photonic Materials and Devices V, edited by J. G. Grote, T. Kaino, 4991 (2003) p. 183.

  16. (a) G. DE LA TORRE, P. VAZQUEZ, F. AGULLO-LOPEZ, and T. TORRES, Chem. Rev. 104 (2004) 3723; (b) G. DE LA TORRE, P. VAZQUEZ, F. AGULLO-LOPEZ and T. TORRES, J. Mater. Chem. 8 (1998) 1671; M. CALVETE, G. Y. YANG and M. HANACK, Synth. Met. 141 (2004) 231; C. G. CLAESSENS, W. J. BLAU, M. COOK, M. HANACK, R. J. M. NOLTE, T. TORRES and D. TORRES, Monat. Chem. 132 (2001) 3.

  17. (a) M. HANACK, H. HECKMANN and R. POLLEY, in “Methods of Organic Chemistry(Houben-Weyl)“, 4th Ed., edited by E. Schaumann, (Thieme, Stuttgart, New York 1997) Vol. E9d, pp. 717; (b) C. C. LEZNOFF, in Phthalocyanines: Properties and Applications, edited by C. C. Leznoff, A. B. P. Lever (VCH Publishers, Inc., New York 1989) Vol. 1, p.1; (c) M. HANACK AND M. LANG, Adv. Mater. 6 (1994) 819.

  18. M. SOMMERAUER, C. RAGER and M. HANACK, J. Am. Chem. Soc. 118 (1996) 10085.

    Article  CAS  Google Scholar 

  19. M. J. STILLMAN and A. J. THOMSON, J. Chem. Soc. Faraday Trans.2. 70 (1974) 790.

    Article  CAS  Google Scholar 

  20. (a) R. D. GEORGE, A. W. SNOW, J. S. SHIRK, W. R. BARGER and J. PORPH, Phthal 2 (1998) 1; (b) B. R. HOLLEBONE and M. J. STILLMAN, J. Chem. Soc., Faraday Trans.2. 74 (1978) 2107; (c) E. S. DODSWORTH, A. B. P. LEVER, P. SEYMOUR and C. C. LEZNOFF, J. Phys. Chem. 89 (1985) 5698; (d) W. J. SCHUTTE, M. SLUYTERS-REHBACH and J. H. SLUYTERS, J. Phys. Chem. 97 (1993) 6069.

    Google Scholar 

  21. S. A. MIKHALENKO, S. V. BARKANOVA, O. L. LEBEDEV and E. A. LUK’YANETS, Zh. Obshch. Khim. 41 (1971) 2735; J. GEN, Chem. USSR 41 (1971) 2770.

    CAS  Google Scholar 

  22. M. HANACK, J. METZ and G. PAWLOWSKI, Chem. Ber. 115 (1982) 2836.

    Article  CAS  Google Scholar 

  23. H. HECKMANN, Ph.D. Thesis, University of Tübingen, Germany (1999).

  24. G. SCHMID, E. WITKE, U. SCHLICK, S. KNECHT and M. HANACK, J. Mater. Chem. 5 (1995) 855.

    Article  CAS  Google Scholar 

  25. J. P. LINSKY, T. R. PAUL, R. S. NOHR and M. E. KENNEY, Inorg. Chem. 19 (1980) 3131.

    Article  CAS  Google Scholar 

  26. M. HANACK and H. HECKMANN, Eur. J. Inorg. Chem. (1998) 367.

  27. G. ROJO, G. MARTIN, F. AGULLO-LOPEZ, T. TORRES, H. HECKMANN and M. HANACK, J. Phys. Chem. B 104 (2000) 7066.

    Article  CAS  Google Scholar 

  28. T. SCHNEIDER, H. HECKMANN, M. BARTHEL and M. HANACK, Eur. J. Org. Chem. (2001) 3055.

  29. (a) E. I. KOVSHEV, V. A. PUCHNOVA, and E. A. LUK’YANETS, Zh. Org. Khim. 7 (1971) 369, J. Org. Chem. USSR. 7 (1971) 364; (b) R. POLLEY and M. HANACK, J. Org. Chem. 60 (1995) 8278; (c) M. KATAYOSE, S.TAI, K. KAMIJIMA, H. HAGIWARA and N. HAYASHI, J. Chem. Soc., Perkin Trans. 2 (1992) 403; (d) K. KITAHARA, T.ASANO, K. HAMANO, S. TOKITA and H. NISHI, J. Heterocyclic Chem., 27 (1990) 2219; (e) M. J. COOK, A. J. DUNN, S. D. HOWE, A. J. THOMSON and K. J. HARRISON, J. Chem. Soc., Perkin Trans I, (1988) 2453; (f)G. I. GONCHAROVA, M. G. GAL’PERN, E. A. LUK’YANETS, Zh. Obshch. Khim. 52 (1982) 666, J. Gen. Chem. USSR 52 (1982) 581.

  30. Z. Z. HO, C. Y. JU, and W. M. HETHERINGTON III, J. Appl. Phys. 62 (1987) 716.

    Article  CAS  Google Scholar 

  31. Y. CHEN, L. R. SUBRAMANIAN, M. BARTHEL and M. HANACK, Eur. J. Inorg. Chem. (2002) 1032.

  32. Y. CHEN, S. M. O’FLAHERTY, M. HANACK and W. J. BLAU, J. Mater. Chem. 13 (2003) 2405.

    Article  CAS  Google Scholar 

  33. S. HUGHES, G. SPRUCE, B. S. WHERRETT and T. KOBAYASHI, J. App. Phys., 81 (1997) 5905.

    Article  CAS  Google Scholar 

  34. (a) G. WINTER, H. HECKMANN, P. HAISCH, W. EBERHARDT, M. HANACK, L. LÜER, H. J. EGELHAAF and D. OELKRUG, J. Am. Chem. Soc. 120 (1998) 11663; P. HAISCH, G. WINTER, M. HANACK, L. LÜER, H. J. EGELHAAF and D. OELKRUG, Adv. Mater. 9 (1997) 316.

  35. F. HENARI, A. DAWEY, W. BLAU, P. HAISCH and M. HANACK, J. Porph. Phthal. 3 (1999) 331.

    Article  CAS  Google Scholar 

  36. M. BARTHEL and M. HANACK, J. Porph. Phthal. 4 (2000) 635.

    Article  CAS  Google Scholar 

  37. M BARTHEL, Ph.D. Thesis, University of Tübingen, Germany (2001).

  38. M. BARTHEL, D. DINI, S. VAGIN and M. HANACK, Eur. J. Org. Chem. (2002) 3756.

  39. N. KOBAYASHI, Coord. Chem. Rev. 219/221 (2001) 99; N. KOBAYASHI and A. MURANAKA, The 50th Annual Meetings of Coordination Chemistry Society, Kusatsu, Japan, September 16–18, 2000.

  40. (a) Y. CHEN, Z. E. HUANG, R. F. CAI and B. C. YU, Eur. Polym. J. 34 (1998) 137; (b) N. B. MCKEOWN, “Phthalocyanine Materials: Synthesis, Structure and Function,” edited by B. DUNN, J. W. GOODBY, A. R. WEST (Cambridge University Press, 1998).

  41. (a) D. G. RODRIGUEZ and T. TORRES, Electrochem. Soc. Proc. 12 (2002) 195; (b) G. BRUSATIN and R. SIGNORINI, J. Mater. Chem. 12 (2002) 1964; (c) S. UCHIDA, J. XUE, B. P. RAND and S. R. FORREST, Appl. Phys. Lett. 84 (2004) 4218.

  42. T. G. LINSSEN, K. DUERR, M. HANACK and A. HIRSCH, J. Chem. Soc. Chem. Commun. (1995) 103.

  43. (a) A. GOULOUMIS, S. G. LIU, A. SAATRE, P. VAZQUEZ, L. ECHEGOYEN and T. TORRES, Chem. Eur. J. 6 (2000) 3600; (b) K. DUERR, S. FIEDLER, T. LINSSEN, A. HIRSCH and M. HANACK, Chem. Ber. 130 (1997) 1375; (c) A. SASTRE, A. GOULOUMIS, P. VAZQUEZ, T. TORRES, V. DOAN, B. J. SCHWARTZ, F. WUDL, L. ECHEGOYEN and J. RIVERA, Org. Lett. 1 (1999) 1807.

  44. (a) Y. CHEN, M. E. EI-KHOULY, M. SASAKI, Y. ARAKI and O. ITO, Org. Lett. 7 (2005) 1613; (b) B. BALLESTEROS, G. D. L. TORRE, T. TORRES, G. L. HUG, G. M. A. RAHMAN, D. M. GULDI, Tetrahedron, in press (doi:10.1016/j.tet.2005.08.126), 2005.

    Article  CAS  Google Scholar 

  45. K. YAMASAKI, O. OKADA, K. INAMI, K. OKA, M. KOTANI and H. YAMADA, J. Phys. Chem. B, 101 (1997) 13.

    Article  CAS  Google Scholar 

  46. Y. CHEN, L. R. SUBRAMANIAN, M. FUJITSUKA, O. ITO, S. O’FLAHERTY, W. J. BLAU, T. SCHNEIDER, D. DINI and M. HANACK, Chem. Eur. J. 8 (2002) 4248.

    Article  CAS  Google Scholar 

  47. V. KRISHNAN, M. P. FETH, E. WENDEL, Y. CHEN, M. HANACK and H. BERTAGNOLLI, Z. Phys. Chem. 218 (2004) 1.

    Article  CAS  Google Scholar 

  48. C. G. CLAESSENS, A. GOULOUMIS, M. BARTHEL, Y. CHEN, G. MARTIN, F. AGULLO-LOPEZ, I. LEDOUX-RAK, J. ZYSS, M. HANACK and T. TORRES, J. Porph. Phthal. 7 (2003) 291.

    Article  CAS  Google Scholar 

  49. J. KLEINWAECHTER and M. HANACK, J. Am. Chem. Soc. 119 (1997) 10684.

    Article  CAS  Google Scholar 

  50. Y. CHEN, M. BARTHEL, M. SEILER, L. R. SUBRAMANIAN, H. BERTAGNOLLI and M. HANACK, Angew. Chem. Int. Ed. Engl. 41 (2002) 3239.

    Article  CAS  Google Scholar 

  51. T. NAGAMURA, A. NAITO, I. YOSHIDA, Y. CHEN, M. HANACK and J. NONLINEAR, Opt. Phys. Mater. 11 (2002) 205.

    Article  CAS  Google Scholar 

  52. H. BERTAGNOLLI and T. S. ERTEL, Angew. Chem. Int. Ed. Engl. 33 (1994) 45.

    Article  Google Scholar 

  53. (a) Y. CHEN. D. DINI, M. HANACK, M. FUJITSUKA and O. ITO, Chem. Commun. (2004) 340; (b) Y. CHEN. Y. ARAKI, M. FUJITSUKA, M. HANACK, O. ITO, S. M. O’FLAHERTY and W. J. BLAU, Sol. State Commun. 131 (2004) 773.

  54. R.-Y. ZHU, Y. CHEN, J. ZHOU, B. LI, W. M. LIU, S. X. QIAN, M. HANACK, Y. ARAKI and O. ITO, Chem. Phys. Lett. 398 (2004) 308.

    Article  CAS  Google Scholar 

  55. M. SHEIK-BAHAE, A. A. SAID and E. W. VAN STRYLAND, Opt. Lett. 14 (1989) 955.

    Article  CAS  Google Scholar 

  56. J. S. SHIRK, Private Communication with (2002).

  57. (a) A. PARTORI, A. M. GLASS, T. H. CHIU and D. T. H. LIU, Opt. Lett. 18 (1993) 906; (b) P. TAYEBATI, E. CANOGLU, C. HANTZIS and R. N. SACKS, Appl. Phys. Lett. 71 (1997) 1610; (c) R. JONES, M. TZIRAKI, P. M. W. FRENCH, K. M. KWOLEK, D. D. NOLTE and M. R. MELLOCH, Opt. Exp. 2 (1998) 439.

  58. (a) T. OKAMOTO, T. KAMIYAMA and I. YAMAGUCHI, Opt. Lett. 18 (1993) 1570; Q. W. SONG, C. -P. ZHANG, R. BLUMER, R. B. GROSS, Z.-P. CHEN and R. R. BIRGE, Opt. Lett. 18 (1993) 1373; (b) D. FICHOU, J.-M. NUNZI, F. CHARRA and N. PFEFFER, Adv. Mater. 6 (1994) 64; (c) A. YACOUBIAN and T. M. AYE, Appl. Opt. 32 (1993) 3073.

  59. (a) T. NAGAMURA, in “Femtosecond Technology,” edited by T. KAMIYA, F. SAITO, O. WADA and H. YAJIMA, Springer Series in Photonics 2 (Springer-Verlag, Berlin Heidelberg, 1999) Part VI-4, p. 376; (b) T. NAGAMURA, H. SAKAGUCHI, AND S. MUTA, Proc. SPIE 2514 (1995) 241; (c) H. INOUE, H. SAKAGUCHI and T. NAGAMURA, Appl. Phys. Lett. 73 (1998) 10.

  60. H. INOUE, D. J. ELLIOT, M. TADA, T. NAGAMURA, F. GRIESER, H. SAKAGUCHI and D. N. FURLONG, Colloids and Surfaces, A: Physicochem. Eng. Aspts. 169 (2000) 233.

    Article  CAS  Google Scholar 

  61. (a) T. NAGAMURA, K. SASAKI, F. IIZUKA, T. ADACHI, and I. YOSHIDA, Opt. Commun. 205 (2002) 107; (b) T. NAGAMURA and T. HAMADA, Appl. Phys. Lett. 69 (1996) 1191; (c) T. NAGAMURA, in “Sensors and Optical Switching (Molecular and Supramolecular Photochemistry Series),” edited by V. Ramamurthy and K. S. Schanze (Marcel Dekker, Inc., New York, 2001) Vol. 7 p. 387; (d) T. NAGAMURA, T. ADACHI, I. YOSHIDA, H. INOUE, H. HECKMANN and M. HANACK, Mol. Cryst. Liq. Cryst. 370 (2001) 97.

  62. A. NAITO, I. YOSHIDA, T. NAGAMURA, Y. CHEN and M. HANACK, Shizuoka Daigaku Denshi Kogaku Kenkyusho Kenkyu Hokoku 37 (2002) 69.

    CAS  Google Scholar 

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Chen, Y., Hanack, M., Blau, W.J. et al. Soluble axially substituted phthalocyanines: Synthesis and nonlinear optical response. J Mater Sci 41, 2169–2185 (2006). https://doi.org/10.1007/s10853-006-5552-9

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