Abstract
The recent progress in the chemistry of electron acceptors of the fluorene series and their applications for electronics and photonics is described, together with results from our laboratory. It is demonstrated that acceptors incorporating electron donating groups that results in intramolecular charge transfer are promising candidates for advanced materials with specific electrical and optical properties.
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References
Hansch, C., Leo, A., and Taft, R.W. (1991),Chem. Rev. 91, 165–195.
Ogura, F., Otsubo, T., and Aso, Y. (1992),Sur Reports 11,439–464.
Khodorkovsky,V.,aitd Becker,J.Y. (1994),in J.-P. Farges (ed.)Organic Conductors. Fundamentals and Applications,Marcel Dekker, New York, pp. 75–114.
Htinig, S. (1995), J. Mater. Chem. 5,1469–1479.
MartÃn, N.,and Seoane,C.(1997),inH.S. Nalwa (ed.)Handbook of Organic Conductive Molecules and Polymers,vol. 1, Wiley, Chichester, pp. 1–86.
MartÃn, N., Segura, J. L., and Seoane, C. (1997),1Mater. Chem. 7,1661–1676.
Zhao, H., Heintz, R.A., Ouyang, X., Grandinetti, G., Cowen, J., Dunbar, K.R. (1999),in J. Veciana, C. Rovira and D.B. Amabilino (eds.)Supramolecular Engineering of Synthetic Metallic Materials: Conductors and Magnets. NATO ASI Series Vol. 518,Kluwer Academic Publishers, Dodrecht, pp. 353–376.
Wudl, F., Yu, H., Fourmigue, M., Hicks, R. (1999), in J. Veciana, C. Rovira and D.B. Amabilino (eds.)Supramolecular Engineering of Synthetic Metallic Materials: Conductors and Magnets. NATO ASI Series Vol.518,Kluwer Academic Publishers, Dordrecht, pp. 393--407.
Strohriegl, P.,and Grazulevicius, J.V. (1997),in H.S.Nalwa (ed.),Handbook of OrganicConductive Molecules and Polymers vol.1, Wiley, Chichester, pp. 553–620.
Shattuck, M. D., and Vahtra, U. (1969), U.S. Patent 3,484,327.
Mukherjee, T.K., and Levasseur, L.A. (1965),J. Org .Chem. 30644–646.
Mukherje, T.K. (1968),Tetrahedron 24721–728.
Mukherje, T.K. (1966),J. Phys. Chem. 703648–3652.
Orchin, M., and Woolfolk, E.O., (1946),J. Am. Chem. Soc. 681727–1729.
Woolfolk, E.O., and Orchin, M. (1955),Org. Syntheses,Coll. Vol. III, 837–838.
Sulzberg, T., and Cotter, R.J. (1970),J. Org . Chem. 352762–2769.
Turner, S.R. (1977), U.S. Patent 4,062,886.
Bloom, M.S., and Groner, C.F. (1977),Research Disclosure,32–36.
Mysyk, D.D., Sivchenkova, N.M., Kampars, V.E., and Neilands, O.Ya (1987),Izv. Akad. Nauk Latv. SSR Ser. Khim.,612–626 (in Russian).
Mysyk, D.D., Perepichka, I.F., and Sokolov, N.I. (1997),J. Chem. Soc. Perkin Trans. 2,537–545.
Kampars, V.E., and Neilands, O.Ya. (1977),Usp. Khim.(Russ. Chem. Rev.) 46945–966 (in Russian).
Kuder, J.E., Pochan, J.M., Turner, S.R., and Hinman, D.-L.F. (1978),J. Electrochem. Soc.: Electrochem. Sci. And Technology 1251750–1758.
Mysyk, D.D., Perepichka, I.F., Edgina, A.S., and Neilands, O.Ya (1991),Latvian J. Chem. 727–735 (in Russian).
Perepichka, I.F., Kuz’mina, L.G., Perepichka, D.F., Bryce, M.R., Goldenberg, L.M., Popov, A.F., and Howard, J.A.K. (1998),J. Org . Chem . 636484–6493.
Perepichka, I.F., Mysyk, D.D., and Sokolov, N.I. (1995),in N.S. Allen, M. Edge, I.R. Bellobonoand E. Selli (eds.),Current Trends in Polymer PhotochemistryEllis Horwood, New York, pp. 318–327.
Mysyk, D.D., Perepichka, I.F., Sivchenkova, N.M., Kampars, V.E., Neilands, O.Ya., andKampare, R.B. (1984),Izv. ANLaty. SSR Ser. Khim.,328–331 (in Russian).
Mysyk, D.D., Sivchenkova, N.M., Kampars, V.E., Neilands, O.Ya., and Kampare, R.B. (1984),Izv. AN Laty. SSR Ser. Khim.332–335 (in Russian).
Weiser, G. (1972),J. Appl. Phys 435028–5033.
Gill, W.D. (1972),J. Appl. Phys. 435033–5040.
Enomoto, T., and Hatano, M. (1974),Makromol. Chem. 17557–65.
Perepichka, I F, Popov, A.F., Artyomova, T.V., Vdovichenko, A.N., Bryce, M.R., Batsanov, A.S., Howard, J.A.K., and Megson, J.L. (1995),J. Chem. Soc. Perkin Trans. 23–5.
Perepichka, I.F., Popov, A.F., Orekhova, T.V., Bryce, M.R., Vdovichenko, A.N., Batsanov, A.S., Goldenberg, L.M., Howard, J.A.K., Sokolov, N.I., and Megson, J.L. (1996),J Chem. Soc. Perkin Trans. 2,2453–2469.
Perepichka, I.F., Mysyk, D.D., and Sokolov, N.I. (1999),Synth. Metals 1019–10.
Perepichka, I.F., Perepichka, D.F., Bryce, M.R., Goldenberg, L.M., Kuz’mina, L.G., Popov, A.F., Chesney, A., Moore, A.J., Howard, J.A.K., and Sokolov, N.I. (1998),Chem. Commun.,819–820.
Perepichka, D.F., Perepichka, I.F., Bryce, M.R., Popov, A.F., Chesney, A., and Moore, A.J. (1998), inStructures of Organic Compounds and Reaction Mechanisms,Inst. Physical Organic & Coal Chemistry, Donetsk, p. 94–100.
Skabara, P.J., Serebryakov, I.M., and Perepichka, I.F. (1999)J. Chem. Soc. Perkin Trans. 2,505–513.
Mysyk, D.D., and Perepichka, I.F. (1994),Phosphorus Sulfur and Silicon 95–96527–529.
Mysyk, D.D., Perepichka, I.F., Perepichka, D.F., Bryce, M.R., Popov, A.F., Goldenberg, L.M., and Moore, A.J. (1999), J. Org . Chem. 646937–6950.
Borsenberger, P.M., and Weiss, D.S. (1998)Organic Photoreceptors for Xerography,Marcel Dekker, New York.
Borsenberger, P.M., and Weiss, D.S. (1993)Organic Photoreceptors for Imaging Systems,Marcel Dekker, New York.
Gill,W.D.(1975),in J. Stuke and W.Brenig(eds.),Amorphous and Liquid Semiconductors,Taylor and Francis, London, p. 135.
Gill,W.D.(1974),in J. Stuke and W. Brenig (eds.),Proceedings of the Fifth International Conference on Amorphous and Liquid Sermiconductors,Taylor and Francis, London, p. 901.
Emeraldt, R.L., and Mort, J. (1974),J. Appl. Phys. 453943–3945.
Turner, S.R. (1980),Macromolecules 13782–785.
Loutfy, R.O., Hsiao, C.-K., Ong, B.S., and Keoshkerian, B. (1984),Can. J. Chem. 621877–1885.
Loutfy, R.O. and Ong, B.S. (1984),Can. J. Chem. 622546–2551.
Ong, B.S., Keoshkerian, B., Martin, T.I., and Hamer, G.K. (1984),Can. J. Chem. 63147–152.
Matsui, M., Fukuyasu, K., Shibata, K., and Muramatsu, H. (1993),J. Chem. Soc. Perkin Trans. 2,1107–1110.
Matsui, M., Shibata, K., Muramatsu, H., and Nakazumi, H. (1996),J. Mater. Chem. 61113–1118.
Turner, S.R., and Pochan, J.M. (1977), U.S. Patent 4,056–391.
Pochan, J.M., and Turner, S.R. (1977), U.S. Patent 4,063–947.
Bulyshev, Yu.S., Kashirskii, I.M., Pashkin, I.I., Andrievskii, A.M., and Tverskoi, V.A. (1990),Khim. Vys. Energ. 24232–236.
Pearson, J.M. (1977),Pure and Appl. Chem. 49463–477.
Skabara, P.J., Serebryakov, I.M., and Perepichka, I.F. (1999),Synth. Metals 1011336–1337.
Pravednikov, A.N., Kotov, B.V., and Tverskoi, V.A. (1978),Zh. Vses. Khim. Obshch. Im D.1. Mendeleeva 23524–536 (in Russian).
Hoegl, H., Barchietto, G., and Tar, D. (1972),Photochem. and Photobiol. 16335–352.
Getmanchuk, Yu.P.; Sokolov, N.Ã.(1983), in Fundamentals of Optical Memory and Medium, issue 14, Vyshcha Shkola, Kiev, pp. 11–20 (in Russian).
Sokolov, N.I., Barabash, Y.M., Poperenko, L.V., Perepichka, I.F., Mysyk, D.D., and Kostenko, L.I. (1997),Proc. SPIE 3055171–180.
Sokolov, N.I., Barabash, Yu.M., Poperenko, L.V., Perepichka, I.F., Mysyk, D.D., and Komarov, V.A. (1998), Functional Materials 5 441–446.
Mysyk, D.D., Perepichka, I.F., Romashev, V.E., Andrievskii, A.M., and Kostenko, L. I. (1986), USSR Patent 1,241,673.
Mysyk, D.D., Perepichka, I.F., Kostenko, L.I., Sokolov, N.I., Perelman, L.A., and Grebenyuk, S.A. (1988), USSR Patent 1,441,718.
Perepichka, I.F., Mysyk, D.D., Sokolov, N.I., and Barabash, Yu.M. (1990), USSR Patent 1,637,244.
Perepichka, I.F., Mysyk, D.D., Sokolov, N.I., and Bazhenov, M.Yu. (1991),USSR Patent 1,658,599.
Perepichka, I.F., Mysyk, D.D., Sokolov, N.I., and Bazhenov, M.Yu. (1992), USSR Patent 1,777,487.
Kostenko, L.I., Perelman, L.A., Perepichka, I.F., Mysyk, D.D., Grebenyuk, S.A., Kotelenets, M.I., Popov, A.F., Sokolov, N.I., Kuvshinsky, N.G., and Bazhenov, M.Yu (1986), USSR Patent 1,228–672.
Kostenko, L.I., Perepichka, I.F., Perelman, L.A., Mysyk, D.D., Grebenyuk, S.A., Popov, A.F., Sokolov, N.I., Kuvshinsky, N.G., and Bazhenov, M.Yu. (1988), USSR Patent 1,441–964.
Manushevich, G.N., Buzurnyuk, S.A., Mysyk, D.D., Kostenko, L.I., Perelman, L.A., Perepichka, I.F., and Sivchenkova, N.M. (1988), USSR Patent 1,471,874.
Bazhenov, M.Yu., Barabash, Yu.M., Perepichka, I.F., Kostenko, L.I., and Sokolov, N. I. (1991), USSR Patent 1,702,850.
Perelman, L.A., Sokolov, N.I., Mysyk, D.D., Kostenko, L.I., Miroshnichenko, A.A., Kharaneko, O.L, Perepichka, I.F., Bazhenov, M.Yu., and Barabash, Yu.M. (1991), USSR Patent 1,729,277.
Perepichka, I. F., Mysyk, D.D., Sokolov, N.I., Kostenko, L.I., Perelman, L.A., Grebenyuk, S.A., Popov, A.F., Bazhenov, M.Yu., and Barabash, Yu.M. (1992), USSR Patent 1,743,300.
Malakhova, I.A., Bodrova, N.A., Pavlov, A.V., Koshelev, K.K., Orlova, L.I., Petrova, M.I., and Perepichka, I.F. (1992), USSR Patent 1,802,969.
Perepichka, I.F., Mysyk, D.D., Sokolov, N.I., Kostenko, L.I., Perelman, L.A., Grebenyuk, S.A., Popov, A.F., Sivchenkova, N.M., Bazhenov, M.Yu., and Barabash, Yu.M. (1992), USSR Patent 1,814,409.
Semenenko, N.M., Abramov, V.N., Kravchenko, N.V., Trushina, V.S., Buyanovskaya, P.G., Kashina, V.L., and Mashkevich, I.V. (1985),Zh. Obsch. Khim. 55324–330.
Abramov, V.N., Andrievskii, A.M.,Bodrova, N.A., Borodkina, M.S., Kravchenko, I.I., Kostenko, L.I., Malakhova, I.A., Nikitina, E.G., Orlov, LG., Perepichka, I.F.,Pototskii,I.S.,Semenenko,N.M.,and Trushina,V.S.(1987),USSR Patent 1,343,760.
Mysyk, D.D., Neilands, O.Ya., Kuvshinsky, N.G., Sokolov, N.I., and Kostenko, L.I. (1987), USSR Patent 1,443,366.
Belonozhko, A.M., Davidenko, N.A., Kuvshinsky, N. G.; Neilands, O.Ya., Mysyk, D.D.,and Prizva, G.I. (1989), USSR Patent 1,499,553.
Mysyk, D.D., Neilands, O.Ya., Khodorkovsky, V.Yu., Kuvshinsky, N.G., Belonozhko, A.M., and Davidenko, N.A. (1991), USSR Patent 1,665,678.
Zhang, Y., Wada, T., and Sasabe, H. (1998),J. Mater. Chem. 8809–828.
Donckers, M.C.J.M., Silence, S.M., Walsch, C.A., Hache, F., Burland, D.M., Moemer, W.E., and Twieg, R.J. (1993),Opt. Lett. 181044–1046.
Silence, S.M., Donckers, M.C.J.M., Walsch, Burland, D.M., Twieg, R.J., and Moemer, W.E. (1994),Appl. Opt. 332218–2222.
Burland, D.M., Bjorklund, W.E., Moemer, W.E., Silence, S.M., and Stankus, J.J. (1995),Pure Appt. Chem. 6733–38.
Burland, D.M., Devoe, R.J., Geletneky, C., Jia, Y., Lee, V.Y., Lundquist, P.M., Moylan, C.R., Poga, C., Twieg, R.J., and Wortmann, R. (1996),Pure Appl. Opt. 5513–520.
Malliaras, G.G., Krasnikov, V.V., Bolink, H.J., and Hadziioannou, G. (1994),Appl. Phys. Lett. 65262–265.
Malliaras, G.G., Krasnikov, V.V., Bolink, H.J., and Hadziioannou, G. (1995),Proc. SPIE 252694.
Malliaras, G.G., Krasnikov, V.V., Bolink, H.J., andHadziioannou, G. (1995),Appl. Phys. Lett.66,1038–1040.
Malliaras, G.G., Krasnikov, V.V., Bolink, H.J., and Hadziioannou, G. (1995),Proc. SPIE2527, 250.
Malliaras, G.G., Krasnikov, V.V., Bolink, H.J., and Hadziioannou, G. (1995),Appl. Phys; Lett.67,455–457.
Malliaras, G.G., Krasnikov, V.V., Bolink, H.J., and Hadziioannou, G. (1995),Phys. Rev. B52,14324–14327.
Malliaras, G.G., Angerman, H., Krasnikov, V.V., ten Brinke, G., and Hadziioannou, G. (1996),J. Phys. D: Appl. Phys. 292045–2048.
Malliaras, G.G., Krasnikov, V.V., Bolink, H.J., and Hadziioannou, G. (1996),Pure Appl. Opt. 5631–643.
Kippelen, K., Sundalphon, K., Peyghambarian, N., Lyon, S.R., Padias, A.B., and Hall, H.K., Jr. (1993),Elect. Lett. 291873–1874.
Meerholz, K., Volodin, B.L., Sundalphon, K., Kippelen, K., and Peyghambarian, N. (1994),Nature 371497–500.
Sundalphon, K., Kippelen, K., Peyghambarian, N., Lyon, S.R., Padias, A.B., and Hall, H.K., Jr. (1994),Opt. Lett. 1968–70.
Volodin, B.L., Meerholz, K., Sundalphon, K., Kippelen, K., and Peyghambarian, N. (1994),Proc. SPIE 214472.
Sundalphon, K., Kippelen, K., Meerholz, K., and Peyghambarian, N. (1996),Appl. Opt. 352346–2354.
Kippelen, K., Sundalphon, K., Meerholz, K., and Peyghambarian, N. (1996),Appl. Phys. Lett. 681748–1750.
Yeh, P. (1987), Appl. Opt. 26, 602–604.
Perepichka, I.F., Perepichka, D.F., Bryce, M.R., Chesney, A., Popov, A.F., Khodorkovsky, V., Meshulam, G., and Kotler, Z. (1999),Synth. Metals 1021558–1559.
Reucroft, P.J., Takahashi, K., and Ullal, H.(1974),Appl. Phys. Lett. 25664–666.
Reucroft, P.J., Takahashi, K., and Ullal, H. (1975),J. Appl. Phys. 465218–5223.
Coronado, E., and Gómez-GarcÃa, C.G. (1998),Chem. Rev. 98273–296.
Day, P., and Kurmoo, M. (1997),J. Mater. Chem. 81291–1295.
Otsubo, T., Aso, Y., and Takimiya, K. (1996),Adv. Mater. 8203–211.
Bryce, M.R. (1995),J. Mater. Chem. 51481–1496.
Ferraris, J.P., Cowan, D.O., Walatka, V.V., and Perlstein, J.H. (1973),J. Am. Chem. Soc. 95948–949.
Horiuchi, S., Yamochi, H., Saito, G., Sakaguchi, K., and Kusunoki, M. (1996),J. Am. Chem. Soc. 119 8604–8622.
Moore, A.J., Bryce, M.R., Batsanov, A.S., Heaton, J.N., Lehmann, C.W., Howard, J.A.K., Robertson, N., Underhil, A.E., and Perepichka, I.F. (1998),J. Mater. Chem. 81541–1550.
Bryce, M.R.,Moore, A.J., Batsanov, A.S., Howard, J.A.K.,Robertson, N., and Perepichka,I.F.(1999),in J.Veciana,C. Rovira and D.B.Amabilino(eds.)Supramolecular Engineering of Synthetic Metallic Materials: Conductors and Magnets. NATO ASI Series Vol. 518,Kluwer Academic Publishers, Dordrecht, pp. 437–449.
Perepichka, I.F., Popov, A.F., Orekhova, T.V., Bryce, M.R., Andrievskii, A.M., Batsanov, A.S., Howard, J.A.K., and Sokolov, N.I.,J. Org .Chem.,submitted.
Gutman, F.E., and Lyons, L.E. (1967)Organic Semiconductors,Wiley, New York.
Mayoh, B., and Prout, C.K. (1972)J. Chem. Soc. Faraday Trans. 268, 1072–1082.
Torrance, J.B. (1979)Acc. Chem. Res. 1279–86. 55
Nalwa, H.S., and Miyata, S. (eds.) (1997) Nonlinear Optics of Organic Molecules and Polymers, CRC Press, Boca Raton.
Bosshard, Ch., Sutter, K., Prêtre, Ph., Hulliger, J., Flörscheimer, M., Kaatz, P., and Günter, P. (1995)Organic Nonlinear Optical Materials (Advances in Nonlinear Optics Series. Vol. 1), Gordon and Breach Publishers, Basel.
Marder, S.R., Sohn, J.E., and Stucky, G.D. (eds.) (1991)Materials for Nonlinear Optics. Chemical Perspectives. ACS Symposium Series 455, ACS, Washington.
Nahata, A., Wu, C., Knapp, C., Lu, V., Shan, J., and Yardley, J.T. (1994)Appl. Phys. Leu. 643371–3373.
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Perepichka, I.F. (2000). Electron Acceptors of the Fluorene Series in Photonics and Electronics: Recent Achievements and Perspectives. In: Kajzar, F., Agranovich, M.V. (eds) Multiphoton and Light Driven Multielectron Processes in Organics: New Phenomena, Materials and Applications. NATO Science Series, vol 79. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-4056-0_27
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