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Part of the book series: NATO ASI Series ((ASHT,volume 52))

Abstract

Basic approaches to deeply coloured polymethine dyes are considered. Synthetic methods, stability, and chemical properties are treated for polymethines containing bridge groups in the chromophore. Colour regularities for these dyes are generalized, taking into account bridge group structures and positions in the chromophore. Special attention is paid to the ability of dyes with bridged chromophores to form associates absorbing light in the near IR region. Comparison analysis is presented for dyes of various constitution with respect to changes in their absorption band shapes, Stokes shift, and fluorescent properties. Effects caused on these characteristics by vibronic and intermolecular interactions are elucidated. The application of near IR dyes (1000-1800 nm) in quantum electronics is covered.

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References

  1. Fabian, J. and Zahradnik, R. (1989) Auf der Suche nach tieffarbigen organischen Verbindungen, Angew. Chem. 101, 693–710.

    Article  CAS  Google Scholar 

  2. Fabian, J., Nakazumi, H., and Matsuoka, M. (1992) Near-Infrared Absorbing Dyes, Chem. Rev. 92, 1197–1226.

    Article  CAS  Google Scholar 

  3. Matsuoka, M. (ed.) (1990) Infrared Absorbing Dyes, Plenum Press, New York.

    Google Scholar 

  4. Daehne, S. and Guertler, O. (1973) Farbe, Stabilität und 1-lalbstufenpotentiale von Polymethinfarbstoffe, J. prakt. Chemie 315, 786–790.

    Article  CAS  Google Scholar 

  5. Koenig, W. (1925) Über den Begriff Polymethinfarbstoffe und eine davon ableitbare allgemeine Farhstofformel als Grundlage einer neuen Systematik der Farbenchemie, J. prakt. Chemie 112, 1–36.

    Article  Google Scholar 

  6. Lewis, G.N. and Calvin, M. (1939) The color of organic substances, Chem. Rev. 25, 273–328.

    Article  CAS  Google Scholar 

  7. Dyadyusha, G.G., Kachkovsky, A.D., and Dekhtyar M.L. (1990) Colour and topology of conjugated systems, J. Mol. Struct. 217, 195–205.

    Article  CAS  Google Scholar 

  8. Kornilov, M.Yu., Dyadyusha, G.G., Zamkovoi, V.I., Dekhtyar M.L., and Kachkovsky, A.D. (1984) Purposeful computer search of heterocycles for synthesis of cyanine dyes, Khim. GeterotsikL Sued., 217–222 (Russ.).

    Google Scholar 

  9. Mikhailenko, F.A., Vasilenko N.P., Kachkovskii, A.D., and Rozhinskii, Yu.I. Effect of polar substituents and polymethine chain length on colour of cyanine dyes of the herv..jc,djindole series, Zh. Org. Khim. 18, 435–441 (Russ.).

    Google Scholar 

  10. Briks, Yu.L., Mikitenko, E.K., and Romanov, N.N. (1997) Some approaches to the construction of new nitrogen-containing heterocyclic end groups for synthesizing polvmethine dyes absorbing in the IR region, Dyes and Pigm. 33, 299–318.

    Article  CAS  Google Scholar 

  11. Detty, M. and Luss, H. (1986) Telluropyrylium dyes. 3. Oxidative halogen addition and tellurium-halogen exchange, Organometallics 5, 2250–2256.

    Article  Google Scholar 

  12. Kudinova, M.A., Derevyanko, N.A., Dyadyusha, G.G., Ishehenko, A.A., and Tolmachev, A.I. (1980) Pyrylocyanines. 11. Symmetric tetraphenyl substituted pyrylo2-cyanines, Khim. Geterotsikl. Soed., 898–902 (Russ.).

    Google Scholar 

  13. Nikolajewski, H.E. and Daehne, S.(1966) Aminolyse von C-C Bindungen, Angew. Chem. 78, 1063.

    Article  Google Scholar 

  14. Althof, H. Bornowski, B. und Daehne, S. (1977) Elektrocyclisehe Synthese von aromatischen Aldehyden aus kettenförmigen Polymethinfarbstoffe, J. prakt. Chemie 319,890–894.

    Article  Google Scholar 

  15. Heseltine, D.W. (1957) Pat. USA 2, 734, 900, Sensitizing dyes. C.A. 51, 913b.

    Google Scholar 

  16. Tolmachev, A.I., Slominskii, Yu.L., and Kudinova, M.A. (1984) Synthesis of polymethine dyes absorbing in the near IR spectral region, Usp. Nauchn. Fotogr. 22, 12–27 (Russ.).

    CAS  Google Scholar 

  17. Makin, S.M., Boiko, I.I., and Shaveygina, O.A. (1977) Synthesis and study of tricarhocyanines containing five-and six-membered cycles in the chromophore, Zh. Org. khirn. 13, 2440–2443 (Russ.).

    CAS  Google Scholar 

  18. Makin, S.M., Shaveygina, O.A., Boiko, T.N., Monich, N.V., and Pomogaev, A.I. (1988) Chemistry of enol ethers. LXXXIII. Synthesis and structure of penta-and hexacarbocyanine dyes containing cyclic fragments in the polymethine chain, Zh. Org. Khim. 24, 835–841 (Russ.).

    CAS  Google Scholar 

  19. Monich, N.V., Krasnava, Zh.A., Levkoev, I.I., and Kucherov, V.F. (1981) Synthesis of thiapenta-and thiahexacarbocyanine dyes from alkoxy substituted polymethine salts with dimethilamine residues, Khim. Geterotsikl. Soed., 1631–1636 (Russ.).

    Google Scholar 

  20. Slominskii, Yu.L., Skulbidenko, A.L., and Tolmachev, A.I. (1975) Chemical conversions of 2-methoxy-l,4-dihydroaromatic compounds. II. Di-(3-methoxy-2,5dihydrophenyl)methane, 2,7-dimethoxy-1,4,5,8,9,10-hexahydroanthracene, and 2,7dimethoxy-1,4,5,8-tetrahydroxanthene, Zh. Org. Khim. 11, 392–397 (Russ.).

    CAS  Google Scholar 

  21. Heilig, G. and Luettke, W. (1986) Laserfarbstoffe. IV. Synthese planar fixierter Nonamethin-Cyaninfarbstoffe, Chem. Ber. 119, 3102–3108.

    Article  CAS  Google Scholar 

  22. Slominskii, Yu.L., Radchenko, I.D., and Chepeleva, L.V. (1992) Tetracarbocyanines derived from henz[c,d]indole, Ukr. Khim. Zh. 58, 686–687 (Russ.).

    CAS  Google Scholar 

  23. Kudinova, M.A., Slominskii, Yu.L., and Tolmachev, A.I. (1983) α-Pyrylotetracarbocyanines, Khim. Geterotsikl. Soed., 1559 (Russ.).

    Google Scholar 

  24. Slominskii, Yu.L., Gromova, G.A., and Zuharovskii, V.M. (1987) Nonamethinecyanines derived from benzimidazole, Ukr. Khim. Zh. 53, 93–94 (Russ.).

    CAS  Google Scholar 

  25. Slominskii, Yu.L., Radchenko, I.D., and Smirnova, A.L. (1992) Polycarbocyanines derived from dihydrothiazole, Ukr. Khim. Zh. 58, 57–60 (Russ.).

    CAS  Google Scholar 

  26. Tolmachev, A.I. and Kudinova, M.A. (1974) Pyrylocyanines 4. Symmetric 2,6diphenylthio-and 2,6-diphenylselenopyrylocyanines, Khim. Geterotsikl. Soed., 49–52 (Russ.).

    Google Scholar 

  27. Reynolds, G.A. and Drexhage, K.H. (1977) Stable heptamethine pyrylium dyes that absorb in the infrared, J. Org. Chem. 42, 885–888.

    Article  CAS  Google Scholar 

  28. Demchuk, M.J., Mikhailov, V.P., Ishchenko, A.A., Kudinova, M.A., Tolmachev, A.I., and Yumashev, K. V. (1984) The influence of the structure of thiopyrylocyanine dyes on the laser yield characteristics with passive mode-locking, Zh. Prikl. Spektrosk. 41, 21–28 (Russ.).

    CAS  Google Scholar 

  29. Voropai, E.S. and Samtsov, M.P. (1995) Effect of photon energy on processes of irreversible conversions of polymethine dyes, Zh. PrikL Spektrosk. 62, 218–228 (Russ.).

    CAS  Google Scholar 

  30. Slominskii, Yu.L. and Shulezhko, L.M. (1974) Tricarbocyanines with hydrocarbon cycles in the chromophore, Ukr. Khim. Zh. 40, 625–629 (Russ.).

    CAS  Google Scholar 

  31. Slominskii, Yu.L., Tolmachev, A.I., and Rodova, I.L. (1974) Tricarbocyanine dyes. Pat. USSR 420, 643 (Cl. CO9b, G 03c) 25.03.1974, Appl. 07.05.1971, Otkryuya, Izobreteniya,Prom. Obraztsy, Tovarnye Znaki 51, 90 (Russ.); C.A. 81, 107372x.

    Google Scholar 

  32. Slominsky, Yu.L., Kachkovski, A.D., Popov, S.V., Nechitailo, L.A., and Ignatiev, N.V. (1991) Anionic polymethine dyes containing vinylene bridge, Dyes and Pigm. 15, 247–254.

    Article  Google Scholar 

  33. Heilig, G. and Luettke, W. (1988) Laserfarbstoffe. VI. Untersuchungen zur Spektroskopie and Stabilitàt konformativ fixierter Nonamethin-Cyaninfarbstoffe, Chem. Ber. 121, 407–410.

    Article  CAS  Google Scholar 

  34. Kachkovski, A.D., Dekhtyar, M.L. (1996) Electronic properties of polymethine systems. Part 4: Electronic structure of polymethine chain, Dyes and Pigm. 30, 43–54.

    Article  CAS  Google Scholar 

  35. Alperovich, M.A., Raikhina, R.D., and Khesin, V.G. (1984) Chemical conversions of polymethine dyes in the ground electronic state, Usp. Nauchn. Fotogr. 22, 65–83 (Russ.).

    CAS  Google Scholar 

  36. Slominskii, Yu.L., Smirnova, A.L., Kudinova, M.A., Efimenko, N.I., and Tolmachev, A.I. (1978) Tetracarbocyanines with cyclic groups, Ukr. Khim. Zh. 44, 838–840 (Russ.).

    CAS  Google Scholar 

  37. Slominskii, Yu.L. and Radchenko, I.D. (1977) Di(aminopolyenyl) ketones and their reactions, Ukr. Khim. Zh. 43, 263–270 (Russ.).

    CAS  Google Scholar 

  38. Kudinova, M.A., Slominskii, Yu.L., Shokodko, I. V., and Tolmachev, A.I. (1985) α-Thiopyrylopentacarbocyanines, Ukr. Khim. Zh. 51, 95–96 (Russ.).

    CAS  Google Scholar 

  39. Tolmachev, A.I., Ishchenko, A.A., Kudinova, M.A., Kurdyukov, V.V., and Slominsky, Yu.L. (1994) Thienyl substituted thiopyrylocyanines: spectral and nonlinear optical properties, Proc. Colorchem-94 Svmp. (Prague), 104–105.

    Google Scholar 

  40. Romanov, N.N., Babichev, F.S., Slominskii, Yu.L., and Tolmachev, A.I. (1977) Investigation of basicity of cyanine dyes with cyclic groups in the chromophore, Dokl. AN USSR, Ser. B, 43–46.

    Google Scholar 

  41. Slominskii, Yu.L., Gromova, G.A., Kachkovski, A.D., and Popov, S.V. (1995) Polymethine dyes with a vinylene bridge in chromophoreProc. 3d Int. Svmp. on Functional Dyes (Santa Kruz, USA), 109.

    Google Scholar 

  42. Derevyanko, N.A., Ishchenko, A.A., Svidro, V.A., Slominskii, Yu.L., and Tolmachev, A.I. (1991) Pyridopyrylocarbocyanines, Zh. Org. Khim. 27, 1561–1569 (Russ.).

    CAS  Google Scholar 

  43. Derevyanko, N.A., Ishchenko, A.A., Slominskii, Yu.L., and Tolmachev, A.I. (1991) First examples of dyes of pyridopyrylo-and py’ridopolycarbocyanine series: synthesis and spectral luminescent properties, Mendeleev Commun., 91–92.

    Google Scholar 

  44. Derevyanko, N.A., Ishchenko, AA., Slominskii, Yu.L., and Tolmachev, A.I. (1991) Synthesis and spectral luminescent properties of highly electron-unsymmetric polymethine dyes, Dokl. ANSSSR 317, 108–112 (Russ.).

    CAS  Google Scholar 

  45. Kudinova, M.A., Slominskii, Yu.L., and Tolmachev, A.I. (1981) Pyrylo-4pentacarbocyanines, Khim. Geterotsikl. Soed., 117.

    Google Scholar 

  46. Slominskii, Yu.L., Radchenko, I.D., and Tolmachev, A.I. (1978) Polymethine dyes with hydrocarbon bridges. Chloro substituted tricarbocyanines, Zh. Org. Khim. 14, 2214–2221 (Russ.).

    CAS  Google Scholar 

  47. Slominskii, Yu.L., Radchenko, I.D., and Tolmachev, A.I. (1979) Polymethine dyes with hydrocarbon hridges.Effect of substituents in the chromophore on tricarbocyanine colour, Zh. Org. Khim. 15, 400–407 (Russ.).

    CAS  Google Scholar 

  48. Narayanan, N. and Patonay, G. (1995) A new method for the synthesis of heptamethine cyanine dyes: synthesis of new near-infrared fluorescent labels, J. Org. Chem. 60, 2391–2395.

    Article  CAS  Google Scholar 

  49. Strekowski, L., Lipowska, M., and Patonay, G. (1992) Substitution reactions of a nucleofugal group in heptamethine cyanine dyes. Synthesis of an isothiocyananto derivative for labeling of proteins with a near-infrared chromophore, J. Org. Chem. 57, 4578–4580.

    Article  CAS  Google Scholar 

  50. Lipowska, M., Patonay, G., and Strekowski, L. (1993) New near-infrared cyanine dyes for labeling of proteins, Synthetic Commun. 23, 3087–3094.

    Article  CAS  Google Scholar 

  51. Shealy, D., Lipowska, M., Lipowski, I., Narayanan, N., Sutter, S., Strekowski, L., and Patonay, G. (1995) Synthesis, chromatographic separation, and characterization of near-infrared labeled DNA oligomers for use in DNA sequencing, Analyt. Chem. 67, 247–251.

    CAS  Google Scholar 

  52. Vompe, A.F. (1984) Synthesis of polycarbocyanines and their conversions, Usp. Nauchn. Fotogr. 22, 5–12 (Russ.).

    CAS  Google Scholar 

  53. Griffiths, I. (1993) The MO design and development of functional dyes materials, in Z. Yoshida and Y. Shirota (eds.), Chemistry of Functional Dyes, Mita Press, Tokyo, pp. 1–9.

    Google Scholar 

  54. Kurdyukov, V.V., Kudinova, M.A., and Tolmachev, A.I. (1996) Pyrylocyanines. 35. Squarylium dyes based on tert-butyl substituted pyrylium and thiopyrylium salts, Khim. Geterotsikl. Soed., 1038–1044 (Russ.).

    Google Scholar 

  55. Tolmachev, A.I., Kurdyukov, V.V., and Kudinova, M.A. (1997) Squarylium dyes derived from pyrylium and thiopyrylium, Zh. Nauchn. Prikl. Fotogr. 42, 32–38.

    CAS  Google Scholar 

  56. Slominskii, Yu.L., Dyadyusha, G.G., Ushenko, I.K., Radchenko, I.D., and Tolmachev, A.I. (1974) Effect of di-and trimethylene bridges in the chromophore on colour of polymethine dyes, Ukr. Khim. Zh. 40, 1163–1168.

    CAS  Google Scholar 

  57. Kudinova, M.A., Maiboroda, E.I., Slominskii, Yu.L., and Tolmachev, A.I. (1993) Pyrylocyanines. 31. Benzopyrylocarbocyanine dyes containing hydrocarbon bridges in chromophore, Khim. Geterotsikl. Soed, 1319–1323.

    Google Scholar 

  58. Dyadyusha, G.G, and Kachkovskii, A.D. (1984) A colour theory for polymethine dyes, Usp. Nauchn. Fotogr. 22, 55–65 (Russ.).

    CAS  Google Scholar 

  59. Slominskii, Yu.L., Efimenko, N.I., Kachkovskii, A.D., Kurkina, L.G., and Tolmachev, A.I. (1986) Thiadicarboc_yanines with five-membered cycles in chromophore, Ukr. Khim. Zh. 52, 301–307 (Russ.).

    CAS  Google Scholar 

  60. Slominskii, Yu.L., Shapiro, B.I., Kachkovskii, A.D., Kurkina, L.G., Radchenko, I.D., Chizhova, M.A., and Tolmachev, A.I. (1988) Polymethine dyes with hydrocarbon bridges in the chromophore. I. Electron levels of thiatricarbocyanines and their relation to the photographic action efficiency, J. Inf. Rec. Mater. 16, 23–31.

    CAS  Google Scholar 

  61. Kachkovskii, A.D. (1989) Constitution and Colour of Polymethine Dyes, Naukova Dumka, Kiev (Russ.).

    Google Scholar 

  62. Slominskü, Yu.L., Popov, S.V., Dyadyusha, G.G., Kachkovskii, A.D., and Tolmachev, A.I. (1985) Polymethine dyes with hydrocarbon bridges in the chromophore. Anionic dyes with o-phenylene group in the chromophore, Zh. Org. Khim. 21, 1950–1959 (Russ.).

    Google Scholar 

  63. Popov, S. V., Radchenko, I.D., and Slominskii, Yu.L. (1991) Merocyanines asorbing in the IR region, Ukr. Khim. Zh. 57, 1182–1187 (Russ.).

    CAS  Google Scholar 

  64. Ishchenko, A.A., Kudinova, M.A., Slominskii, Yu.L., and Tolmachev, A.I. (1986) Absorption bandwidths of meso-substituted thiopyrylo-4-tricarbocyanines, Ukr. Khim. Zh. 52, 1175–181 (Russ.).

    Google Scholar 

  65. Foerster, Th. (1940) Quantenmechanischen Rechnungen zur Theorie der organischen Farbstoffe, Z. Phys. Chem. B 48, 12–16.

    Google Scholar 

  66. Dewar, M.J. (1950) Colour and constitution. Part I. Basic dyes, J. Chem. Soc., 2329–2334.

    Google Scholar 

  67. Yasui, S., Matsuoka, M., and Kitao, T. (1988) Syntheses and some properties of infrared-absorbing croconium and related dyes, Dyes and Pigm. 10, 13–22.

    Article  CAS  Google Scholar 

  68. Ishchenko, A.A., Kudinova, M.A., Slominskii, Yu.L., and Tolmachev, A.I. (1986) Pyrylopolycarbocyanines with cyclic groups, Zh. Org. Khim. 22, 170–179 (Russ.).

    CAS  Google Scholar 

  69. Ishchenko, A.A. (1994) Structure and Spectral Luminescent Properties of Polymethine Dyes, Naukova Dumka, Kiev (Russ.).

    Google Scholar 

  70. Dyadyusha, G G, Ishchenko, A.A., Derevyanko, N.A., Kudinova, M.A., and Tolmachev, A.I. (1979) Study of solvatochromism of cyanine dyes by the method of moments, Teor. Eksp. Khim. 15, 412–416 (Russ.).

    CAS  Google Scholar 

  71. Ishchenko, A.A., Derevyanko, N.A., Zubarovskii, V.M., and Tolmachev, A.I. (1984) The effect of polymethine chain length on absorption band widths of symmetric cyanine dyes, Teor. Eksp. Khim. 20, 443–451 (Russ.).

    CAS  Google Scholar 

  72. Reichardt, Ch. (1994) Solvatochromic dyes as solvent polarity indicators, Chem. Rev. 94, 2319–2358.

    Article  CAS  Google Scholar 

  73. Derevyanko, N.A., Dyadyusha, G.G., Ishchenko, A.A., and Tolmachev, A.I. (1983) Influence of solvent nature on position, intensity, and shape of absorption bands of polymethine dyes, Teor. Eksp. Khim. 19, 169–178 (Russ.).

    CAS  Google Scholar 

  74. Ishchenko, A.A., Svidro, V.A., Derevyanko, N.A., Slominskii, Yu.L., and Tolmachev, A.I. (1989) Four-level scheme of electron states and vibronic spectra of benzopyrylo-2monomethinecyanines, Opt. Spektrosk. 66, 1302–1306 (Russ.).

    CAS  Google Scholar 

  75. James, T.H. (1977) The Theory of the Photographic Process, Macmillan Publishing Co., New York, V. 4.

    Google Scholar 

  76. Heilig, G. and Lüttke, W. (1987) Synthese planar fixierter Heptamethin Cyaninfarbstoffe, Chem. Ber. 120, 1863–1866.

    Article  CAS  Google Scholar 

  77. Ishchenko, A.A., Zubarovskii, V.M., Gromova G.A., and Derevyanko, N.A. (1987) Effect of the polymethine chain length on absorption spectra of unsymmetric cyanine dyes, Zh. Org. Khim. 23, 621–630 (Russ.).

    CAS  Google Scholar 

  78. Ishchenko, A.A., Derevyanko, N.A., and Svidro, V.A. (1992) Constitution and fluorescence spectra of unsynunetric polymethine dyes, Dyes and Pigm. 19, 169–177.

    Article  CAS  Google Scholar 

  79. Bondar, M. V., Derevyanko, N.A., Dyadyusha, G.G., Zubarovskii, V.M., Ishchenko, A.A., Przhonskaya, O.V., Slominskii, Yu.L., Smirnova, A.L., Tikhonov, E.A., and Tolmachev, A.I. (1984) Light generation in the near IR region with the use of nonsymmetric polymethine dye solutions, Kvantovaya Elektronika 11, 462–271 (Russ.).

    CAS  Google Scholar 

  80. Ishchenko, A.A, Dokukina, A.F., Smimova, Z.A., and Tolmachev, A.I. (1985) The chemical structure and absorption band shape for polymer dyes in a polymer matrix, Dokl. AN SSSR 284, 1407–1411 (Russ.).

    CAS  Google Scholar 

  81. Slominskii, Yu.L., Gromova G.A., and Smimova, A.L. (1996) Polycarbocyanines forming J-aggregates in solutions, Proc. 4th Symp. “Physics and Chemistry of Polymethine Dyes” (Moscow), 100–101 (Russ.).

    Google Scholar 

  82. Babenko, V.A., Kudinova, M.A., Malyshev, V.I., Slominskii, Yu.L., Sychev, A.A., and Tolmachev, A.I. (1986) New IR fluorescence bands in concentrated polymethine dye solutions and prospects for development of new lasers, Kvantovaya Elektronika 13, 575–581 (Russ.).

    CAS  Google Scholar 

  83. Kudinova, M.A., Ishchenko, A.A, Kurdyukov, V.V., and Tolmachev, A.I. (1990) Pyrylocyanines. 26. Symmetric di-tert-butyldiphenyl substituted pyrylo-2-cyanines, Khim. Geterotsikl. Soed., 902–908 (Russ.).

    Google Scholar 

  84. Babenko, V.A. and Sychev, A.A. (1991) Dyes of IR range in quantum electronics and nonlinear optics, Tr. Fiz. Inst. ANSSSR 212, 144–155 (Russ.).

    CAS  Google Scholar 

  85. Bareika, B.F., Danielius, R.V., Dikchius, G.A., Dyadyusha, G.G., Ishchenko, A.A., Kudinova, M.A., Piskarskas, A.-P.S., Sirutkaitis, V.A., and Tolmachev, A.I. (1982) Effect of solvents on polymethine relaxation times in the picosecond region, Kvantovaya Elektronika 9, 2289–2295 (Russ.).

    CAS  Google Scholar 

  86. Kopainsky, B., Oriu, P., Kaiser, W., Sens, B., and Drexhage, K.H. (1982) Lifetime, photostability, and chemical structure of IR heptamethine cyanine dyes absorbing beyond 1 mm, Appl. Phys. B 29, 15–18.

    Google Scholar 

  87. Ishchenko, A.A. (1994) Laser media based on polymethine dyes, Kvantovaya Elektronika 21, 513–534 (Russ.).

    CAS  Google Scholar 

  88. Ishchenko, A.A. (1996) Structures of terminal heterocyclic groups and fluorescent spectral properties of polymethine dyes, Russ. Chem. Bull. 45, 2079–2089 (Russ.).

    Article  Google Scholar 

  89. Demchuk, M.I., Mikhailov, V.P., Gilev, A.K., Ishchenko, A.A., Kudinova, M.A., Slominskii, Yu.L., and Tolmachev, A.I. (1985) Optimization of passive mode locking regimes for the yttrium aluminate laser, Zh. Prikl. Spektrosk. 41, 718–723 (Russ.).

    Google Scholar 

  90. Kudinova, M.A., Kurdyukov, V.V., Ishchenko, A.A., and Tolmachev, A.I. (1992) Pyrylocyanines. 29. tert-Butyl substituted benzopyrylocyanines, Khim. Geterotsikl. Soed., 339–344 (Russ.).

    Google Scholar 

  91. Bezrodnyi, V.I., Ponezha, E.A., and Tikhonov, E.A. (1978) A new passive Q-switch for Nd3+ lasers, Kvantovaya Elektronika 5, 68–74. (Russ.).

    CAS  Google Scholar 

  92. Grigonis, R., Ishchenko, A.A., Sinkevichius, G., Sirutkaitis, V., and Slominskii, Yu.L. (1991) Investigation of the relaxation times of new cyanine dyes, Laser and Ultrafast Processes 4, 197–199.

    Google Scholar 

  93. Lisitsyn, V.N., Pestryakov, E.V., Trunov, A.I., Kudinova, M.A., Slominskii, Yu.L., and Tolmachev, A.I. (1982) Picosecond pulse generation in the YAG:Nd3+ laser at 1.318 mcm with passive mode locking, Pis’ma Zh. Tekhn. Fiz. 8, 488–492 (Russ.).

    CAS  Google Scholar 

  94. Demchuk, M.I., Mikhailov, V.P., Manichev, I.A., Yumashev, K.V., Ishchenko, A.A., and Slominskii, Yu.L. (1988) Simultaneous generation ofultrashort pulses in the YAG:Nd3+ laser at two generation transitions, Zh. Prikl. Spektrosk. 48, 318–320 (Russ.).

    CAS  Google Scholar 

  95. Derevyanko, N.A., Ishehenko, A.A., Kuchma, LG., Mak, A.A., Murzin, A.G., Pivinskii, E.G., Prilezhaev, D.S., Slominskii, Yu.L., Smirnova, Z.A., Tolmachev, A.I., and Fromzel’. V.A. (1989) Fast-relaxing passive Q-switch based on polymethine dyes for erbium laser with 1.54 wavelength, Opt. Spektrosk. 67, 920–926 (Russ.).

    CAS  Google Scholar 

  96. Ishchenko, A.A., Slominskii, Yu.L., Tolmachev, A.I., Demchuk, M.I., Mikhailov, V.P., and Yumashev, K.V. (1988) Relaxation times of passive Q-switches based on polymethine dyes in liquid and polymer media, Opt. Spektrosk. 64, 653–656 (Russ.).

    CAS  Google Scholar 

  97. Dyadyusha, G.G., Ishchenko, A.A., Derevyanko, N.A., and Tolmachev, A.I. (1982) Study of ionic equilibria of indotricarbocyanines in aromatic hydrocarbons, Dokl. AN SSSR 264, 351–355 (Russ.).

    CAS  Google Scholar 

  98. Ishchenko, A.A., Kramarenko, F.G., Maidannik, A.G., Sereda, S.V., and Vasilenko, N.P. (1991) Structure and association of carbocyanines of the benz[c,d]indole series in binary mixtures of solvents, J. Inf. Rec. Mater. 19, 207–219.

    Google Scholar 

  99. Komarov, I.V., Turov, A.V., Ishchenko, A.A., Derevyanko, N.A., and Kornilov, M. Yu. (1989) Investigation of structure of cationic cyanine dye ion pairs using lanthanide chelates and NMR of quadrupolar nuclei, Dokl. AN SSSR 306, 1134–1137 (Russ.).

    CAS  Google Scholar 

  100. Demchuk, M.I., Ishchenko, A.A., Mikhailov, V.Y., and Avdeeva, V.I. (1988) The influence of the anion on the excited-state relaxation time of cationic polymethine dyes, Chem, Phys. Lett. 144, 99–103.

    CAS  Google Scholar 

  101. Tatikolov, A.S., Shvedova, L.A., Derevyanko, N.A., Ishchenko, A.A., and Kuzmin, V.A. (1992) The influence of counterion on photochemistry of cationic indopolycarbocyanine dyes in ion pairs. Chem, Phys. Lett. 190,291–297.

    CAS  Google Scholar 

  102. Tatikolov, A.S., Derevyanko, N.A., Ishchenko, A.A., Baraldi, I., Caselli, M., Momicchioli, F., and Ponterini, G. (1995) Photoisomerization of asymmetric indobenzimidazolo cyanine dyes, Ber. Bunsenges. Phys. Chem. 99, 763–769.

    Article  CAS  Google Scholar 

  103. Tatikolov, A.S., Dzhulibekov, Kh.S., Shvedova, L.A., and Kuzmnin, V.A. (1995) Influence of “inert” counterions on the photochemistry of some cationic polymethine dyes, J Phys. Chem. 99, 6525–6529.

    Article  CAS  Google Scholar 

  104. Demchuk, M.I., Ishchenko, A.A., Krasnaya, Zh.A., and Mikhailov, V.P. (1990) The excited-state relaxation times of cationic-anionic polymethine dyes, Chen. Phys. Lett. 167,170–174.

    Article  CAS  Google Scholar 

  105. Demchuk, M.I., Mikhailov, V.P., Pavlovich, V.S., Yumashev, K.V., Ishchenko, A.A., Eremeeva E.P., Smirnova, Z.A., and Tolmachev, A.I. (1986) Structural dependence of parameters of passive film Q-switches based on thiopyrylotricarbocyanines, Khhn. Fizika 5, 1184–1192 (Russ.).

    CAS  Google Scholar 

  106. Bezrodnyi, V.I., Ishchenko, A.A., Karabanova, L.A., and Slominskii, Yu.L. (1995) I Iighly stable polymethine-dye-based polymer switches for passive mode locking in neodymium lasers, Kvantovaya Elektronika 22, 849–852 (Russ.).

    CAS  Google Scholar 

  107. Grigonis, R., Eidenas, M., Sirutkaitis, V., Bezrodnyi, V., Ishchenko, A., and Slominskii, Yu. (1996) relaxation times of new passive polymer switches for 1.06 mm, in O. Svelto, S. De Silvestri, and G.Denardo (eds.), Ultrafast Processes in Spectroscopy, Plenum Press, New York, pp. 449–453.

    Chapter  Google Scholar 

  108. Bezrodnyi, V.I., Derevyanko, N.A., Ishchenko, A.A., and Slominskii, Yu.L. (1995) Polymer passive laser switches for stimulated emission in the region of 1.3 mm, Kvantovaya Elektronika 22, 853–855 (Russ.).

    CAS  Google Scholar 

  109. Bezrodnyi, V.I., Derevyanko, N.A., Ishchenko, A.A., Karabanova, LA., Plisko, T.A., Slominskii, Yu.L., and Smirnova, A.L. (1996) Polymethine-dye-based absorption light filters for protection against laser radiation with the wavelength 1060 nm, J. Optical Technology, No. 12, 77–82.

    Google Scholar 

  110. Ishchenko, A.A. (1997) New aspects of luminescence of polymethine dyes, Zh. Nauchn. Prikl. Fotogr. 42, 60–68.

    CAS  Google Scholar 

  111. Bahenko, V.A. and Sychev, A.A. (1996) Efficient emission of 1.1–1.5 mm radiation from a supertluorescent laser with IR dyes in a solid host, Kvantovava Elektronika 23, 413–416 (Russ.).

    Google Scholar 

  112. Polland, H.J., Elsaesser, T., Seilmeier, A., Kaiser, W., Kussler, M., Marx, N.J., Sens, B., and Drexhage, K.II. (1983) Picosecond dye laser emission in the infrared between 1.4 and 1.8 mm, Appl. Phys. B 32, 53–57.

    Google Scholar 

  113. Babenko, V.A. and Sychev, A.A. (1987) Excited molecular complexes in dye solutions and near-IR exciplex lasers, Kvantovaya Elektronika 14, 2179–2185 (Russ.).

    CAS  Google Scholar 

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Tolmachev, A.I., Slominskii, Y.L., Ishchenko, A.A. (1998). New Cyanine Dyes Absorbing in the NIR Region. In: Daehne, S., Resch-Genger, U., Wolfbeis, O.S. (eds) Near-Infrared Dyes for High Technology Applications. NATO ASI Series, vol 52. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-5102-3_19

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