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Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE ve PKloranil ile Yük-Transfer Kompleksleşmeleri

Year 2012, Volume: 14 Issue: 1, 40 - 49, 01.06.2012

Abstract

Karbazol (Cz), 9,9’-dikarbazil (DCz), 3,9’;9,9’’-trikarbazil (TCz) ve policarbazilin (PCz) tetrasiyanoetilen (TCNE) ve p-kloranil (p-CHL) akseptörleriyle yük-transfer (CT) kompleksleşmeleri spektroskopik olarak incelenmiştir. CT komplekslerinin bağıl kararlılıkları, termodinamik özellikleri ve stökiyometrileri donör moleküllerin moleküler yapılarını ve akseptör moleküllerin bağıl elektron ilgilerini temel alarak tartışılmıştır. Çalışma sonucunda DCz, TCz, ve PCz nin TCNE ve p-CHL ile monomerik analoğu olan Cz ye göre daha kararsız kompleks oluşturdukları sonucuna varılmıştır

References

  • [1]. Topsøe, H., Clausen, B.S., Massoth, F.E., Hydrotreating Catalysis - Science and Technology, 11, Anderson, J.R, Boudart, M., Ed., Springer Verlag: Berlin, (1996).
  • [2]. Kayser, K.J., Kilbane, J.J., Method for metabolizing carbazole in petroleum, US Patent 6943006, (2005).
  • [3]. Niziol, J., Gondek, E., Plucinski, K.J., Journal of Material ScienceMaterial Electronics, DOI 10.1007/s10854-009-0039-5.
  • [4]. Labudzinska, A., Galka S., Gorczynska, K., Studies of the carbazole azo dyes by means of UV/VIS spectroscopy, Journal of Molecular Structure, 294, 247-250, (1993).
  • [5]. Segall, A.I., Vitale, M.F., Perez, V.L., Pizzorno, M.T., HPLC analysis of 5Hbenzo[a]carbazole with antifungal activity, Journal of Pharmaceutical and Biomedical Analysis, 31, 1021-1026, (2003).
  • [6]. Gibson, H.W., Olin, G.R., Pochan, J.M., Linear free energy relationships. X. synthesis, thermal, spectral, electrochemical and hole transport (properties) of some novel carbazole derivatives, Journal of Chemical Society, Perkin Transactions II, 1267-1273, (1981).
  • [7]. Grigoras, M., Antonoaia, N.C., Synthesis and characterization of some carbazolebased imine polymers, European Polymer Journal, 41, 1079-1089, (2005).
  • [8]. Fuhrmann, T., Tsutsui, T., Synthesis and properties of a hole-conducting, photopatternable molecular glass, Chemistry of Materials, 11, 2226-2232, (1999).
  • [9]. Strohriegl, P., Kreger, K., Hanft, D., Sonntag, M., Setayesh, S., de Leeuw, D., Novel star-shaped triphenylamine-based molecular glasses and their use in OFETs, Chemistry of Materials, 17, 3031-3039, (2005).
  • [10]. Grigalevicius, S., Ostrauskaite, J., Grazulevicius, J.V., Gaidelis, V., Jankauskas, V., Sidaravicius, J., Cross-linkable photoluminescent hole-transporting molecular glasses, Materials Chemistry and Physics, 77, 281-284, (2003).
  • [11]. Perkin, W.H., Tucker, S.H., The oxidation of carbazole, Journal of Chemical Society, Transactions, 119, 216 (1921).
  • [12]. Robinson, B., Tricarbazyl, Nature, 210, 520-521 (1966). [13]. Hsiao, C.-K., Hor, A.-M., Baranyi, G., Goodbrand, H.B., Imaging members, U.S. Patent 6194110 (2001).
  • [14]. Iwatsuki, S., Arai, K., Polymer effect on the electron-donating character of a polymeric donor, 3. Formation of charge-transfer complexes between polymer containing carbazolyl groups and three kinds of common acceptors, Die Makromolekulare Chemie, 178, 2307-2319 (1977).4
  • [15]. Benesi, H.A., Hildebrand, J.M., A spectropfotometric investigation of the interaction of iodine with aromatic hydrocarbons, Journal Of The American Chemical Society, 71, 2703-2707, (1949).
  • [16]. Job, P., Formation and stability of inorganic complexes in solution, Annali di Chimica Applicata, 9, 113-203, (1928).
  • [17]. Levina, F.A., Sidaravichyus, I., Peredereeva, S.I., Orlov, I.G., Zaikov, G.E., Cherkashin, M.I., Spectrophotometric investigation of donor-acceptor complexes of polyvinylcarbazole, Russian Chemical Bulletin, 20, 49-52, (1971).
  • [18]. Bressler, D.C., Fedorak, P.M., Pickard, M.A., Oxidation of carbazole, N-ethyl carbazole, fluorene, and dibenzothiophene by the laccase of Coriolposis gallica UAMH 8260, Biotechnology Letters, 22, 1119-1125, (2000)
  • [19]. Chowdhury, S., Kebarle, P., Electron affinities of di- and tetracyanoethylene and cyanobenzenes based on measurements of gas-phase electron-transfer equilibria, Journal of the American Chemical Society, 108, 5453-5459, (1986).
  • [20]. Saito, G., Matsunaga, Y., The electron-acceptor strengths of some substituted naphtoquinones, Bulletin of the Chemical Society of Japan, 44, 1788-1791, (1971).
  • [21]. Mulliken, R.S., Person, W.B., Molecular Complexes: A Lecture and Reprint Volume, Wiley Interscience: New York, (1969).
  • [22]. Dewar, M.J.S., Zoebisch, E.G., Healey, E.F., Stewart, J.J.P., Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model, Journal of the American Chemical Society, 107, 3902-3909, (1985).
  • [23]. HyperChem 8.05 for Windows, 2008, Hypercube Inc., 1115 NW 4th Street, Gainesville, FL 32601, USA.
  • [24]. Turro, N.J., Ramamurthy, V., Scaiano, J.C., Principles of Molecular Photochemistry, University Science Books: Sausalito, California, p.179, (2009).
  • [25]. Haderski, G.J., Chen, Z., Krafcik, R.B., Masnovi, J., Baker, R.J., Towns, R.L.R., Donor-acceptor complexes of alkylcarbazole and dicarbazolyl alkane donors with the acceptors tetracyanoethylene and tetranitromethane, The Journal of Physical Chemistry B, 104, 2242-2250, (2000).
  • [26]. Asker, E., Masnovi, J., Charge-transfer complexations of 1,n-di (9-ethylcarbazol- 3-yl) alkanes with tetracyanoethylene and tetranitromethane, Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 71A, 1973-1978, (2009).
  • [27]. Boyer, G., Claramunt, R.M., Elguero, J., Fathalla, M., Foces-Foces, C., Jaime, C., Llamas-Saiz, A.L., Synthesis and structure of new hosts related to 9,9’-bianthryl, Journal of the Chemical Society, Perkin Transactions II, 757-766, (1993)

Charge-Transfer Complexations of Oxidative Coupling Products of Carbazole with TCNE and P- Chloranil

Year 2012, Volume: 14 Issue: 1, 40 - 49, 01.06.2012

Abstract

Charge-transfer (CT) complexations of 9H-carbazole (Cz), 9,9’-dicarbazyl (DCz), 3,9’;9,9’’-tricarbazyl tetracyanoethylene spectroscopically. The relative stabilities, thermodynamic properties and stoichiometries of the CT complexes were discussed based on the molecular structure of the donor molecules and relative electron affinities of the acceptor molecules. It is concluded that DCz, TCz, and PCz form less stable complexes with TCNE and p-CHL than their monomeric analogues Cz

References

  • [1]. Topsøe, H., Clausen, B.S., Massoth, F.E., Hydrotreating Catalysis - Science and Technology, 11, Anderson, J.R, Boudart, M., Ed., Springer Verlag: Berlin, (1996).
  • [2]. Kayser, K.J., Kilbane, J.J., Method for metabolizing carbazole in petroleum, US Patent 6943006, (2005).
  • [3]. Niziol, J., Gondek, E., Plucinski, K.J., Journal of Material ScienceMaterial Electronics, DOI 10.1007/s10854-009-0039-5.
  • [4]. Labudzinska, A., Galka S., Gorczynska, K., Studies of the carbazole azo dyes by means of UV/VIS spectroscopy, Journal of Molecular Structure, 294, 247-250, (1993).
  • [5]. Segall, A.I., Vitale, M.F., Perez, V.L., Pizzorno, M.T., HPLC analysis of 5Hbenzo[a]carbazole with antifungal activity, Journal of Pharmaceutical and Biomedical Analysis, 31, 1021-1026, (2003).
  • [6]. Gibson, H.W., Olin, G.R., Pochan, J.M., Linear free energy relationships. X. synthesis, thermal, spectral, electrochemical and hole transport (properties) of some novel carbazole derivatives, Journal of Chemical Society, Perkin Transactions II, 1267-1273, (1981).
  • [7]. Grigoras, M., Antonoaia, N.C., Synthesis and characterization of some carbazolebased imine polymers, European Polymer Journal, 41, 1079-1089, (2005).
  • [8]. Fuhrmann, T., Tsutsui, T., Synthesis and properties of a hole-conducting, photopatternable molecular glass, Chemistry of Materials, 11, 2226-2232, (1999).
  • [9]. Strohriegl, P., Kreger, K., Hanft, D., Sonntag, M., Setayesh, S., de Leeuw, D., Novel star-shaped triphenylamine-based molecular glasses and their use in OFETs, Chemistry of Materials, 17, 3031-3039, (2005).
  • [10]. Grigalevicius, S., Ostrauskaite, J., Grazulevicius, J.V., Gaidelis, V., Jankauskas, V., Sidaravicius, J., Cross-linkable photoluminescent hole-transporting molecular glasses, Materials Chemistry and Physics, 77, 281-284, (2003).
  • [11]. Perkin, W.H., Tucker, S.H., The oxidation of carbazole, Journal of Chemical Society, Transactions, 119, 216 (1921).
  • [12]. Robinson, B., Tricarbazyl, Nature, 210, 520-521 (1966). [13]. Hsiao, C.-K., Hor, A.-M., Baranyi, G., Goodbrand, H.B., Imaging members, U.S. Patent 6194110 (2001).
  • [14]. Iwatsuki, S., Arai, K., Polymer effect on the electron-donating character of a polymeric donor, 3. Formation of charge-transfer complexes between polymer containing carbazolyl groups and three kinds of common acceptors, Die Makromolekulare Chemie, 178, 2307-2319 (1977).4
  • [15]. Benesi, H.A., Hildebrand, J.M., A spectropfotometric investigation of the interaction of iodine with aromatic hydrocarbons, Journal Of The American Chemical Society, 71, 2703-2707, (1949).
  • [16]. Job, P., Formation and stability of inorganic complexes in solution, Annali di Chimica Applicata, 9, 113-203, (1928).
  • [17]. Levina, F.A., Sidaravichyus, I., Peredereeva, S.I., Orlov, I.G., Zaikov, G.E., Cherkashin, M.I., Spectrophotometric investigation of donor-acceptor complexes of polyvinylcarbazole, Russian Chemical Bulletin, 20, 49-52, (1971).
  • [18]. Bressler, D.C., Fedorak, P.M., Pickard, M.A., Oxidation of carbazole, N-ethyl carbazole, fluorene, and dibenzothiophene by the laccase of Coriolposis gallica UAMH 8260, Biotechnology Letters, 22, 1119-1125, (2000)
  • [19]. Chowdhury, S., Kebarle, P., Electron affinities of di- and tetracyanoethylene and cyanobenzenes based on measurements of gas-phase electron-transfer equilibria, Journal of the American Chemical Society, 108, 5453-5459, (1986).
  • [20]. Saito, G., Matsunaga, Y., The electron-acceptor strengths of some substituted naphtoquinones, Bulletin of the Chemical Society of Japan, 44, 1788-1791, (1971).
  • [21]. Mulliken, R.S., Person, W.B., Molecular Complexes: A Lecture and Reprint Volume, Wiley Interscience: New York, (1969).
  • [22]. Dewar, M.J.S., Zoebisch, E.G., Healey, E.F., Stewart, J.J.P., Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model, Journal of the American Chemical Society, 107, 3902-3909, (1985).
  • [23]. HyperChem 8.05 for Windows, 2008, Hypercube Inc., 1115 NW 4th Street, Gainesville, FL 32601, USA.
  • [24]. Turro, N.J., Ramamurthy, V., Scaiano, J.C., Principles of Molecular Photochemistry, University Science Books: Sausalito, California, p.179, (2009).
  • [25]. Haderski, G.J., Chen, Z., Krafcik, R.B., Masnovi, J., Baker, R.J., Towns, R.L.R., Donor-acceptor complexes of alkylcarbazole and dicarbazolyl alkane donors with the acceptors tetracyanoethylene and tetranitromethane, The Journal of Physical Chemistry B, 104, 2242-2250, (2000).
  • [26]. Asker, E., Masnovi, J., Charge-transfer complexations of 1,n-di (9-ethylcarbazol- 3-yl) alkanes with tetracyanoethylene and tetranitromethane, Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 71A, 1973-1978, (2009).
  • [27]. Boyer, G., Claramunt, R.M., Elguero, J., Fathalla, M., Foces-Foces, C., Jaime, C., Llamas-Saiz, A.L., Synthesis and structure of new hosts related to 9,9’-bianthryl, Journal of the Chemical Society, Perkin Transactions II, 757-766, (1993)
There are 26 citations in total.

Details

Other ID JA22DB85CF
Authors

Erol Asker This is me

Fahrettin Filiz This is me

Ece Uzkara This is me

Orhan Zeybek This is me

Submission Date June 1, 2012
Publication Date June 1, 2012
Published in Issue Year 2012 Volume: 14 Issue: 1

Cite

APA Asker, E., Filiz, F., Uzkara, E., Zeybek, O. (2012). Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE ve PKloranil ile Yük-Transfer Kompleksleşmeleri. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 14(1), 40-49.
AMA Asker E, Filiz F, Uzkara E, Zeybek O. Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE ve PKloranil ile Yük-Transfer Kompleksleşmeleri. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi. June 2012;14(1):40-49.
Chicago Asker, Erol, Fahrettin Filiz, Ece Uzkara, and Orhan Zeybek. “Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE Ve PKloranil Ile Yük-Transfer Kompleksleşmeleri”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 14, no. 1 (June 2012): 40-49.
EndNote Asker E, Filiz F, Uzkara E, Zeybek O (June 1, 2012) Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE ve PKloranil ile Yük-Transfer Kompleksleşmeleri. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 14 1 40–49.
IEEE E. Asker, F. Filiz, E. Uzkara, and O. Zeybek, “Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE ve PKloranil ile Yük-Transfer Kompleksleşmeleri”, Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, vol. 14, no. 1, pp. 40–49, 2012.
ISNAD Asker, Erol et al. “Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE Ve PKloranil Ile Yük-Transfer Kompleksleşmeleri”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 14/1 (June2012), 40-49.
JAMA Asker E, Filiz F, Uzkara E, Zeybek O. Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE ve PKloranil ile Yük-Transfer Kompleksleşmeleri. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi. 2012;14:40–49.
MLA Asker, Erol et al. “Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE Ve PKloranil Ile Yük-Transfer Kompleksleşmeleri”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, vol. 14, no. 1, 2012, pp. 40-49.
Vancouver Asker E, Filiz F, Uzkara E, Zeybek O. Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE ve PKloranil ile Yük-Transfer Kompleksleşmeleri. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi. 2012;14(1):40-9.