BibTex RIS Kaynak Göster

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

Yıl 2012, Cilt: 14 Sayı: 1, 40 - 49, 01.06.2012

Öz

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

Kaynakça

  • [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

Yıl 2012, Cilt: 14 Sayı: 1, 40 - 49, 01.06.2012

Öz

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

Kaynakça

  • [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)
Toplam 26 adet kaynakça vardır.

Ayrıntılar

Diğer ID JA22DB85CF
Bölüm Araştırma Makalesi
Yazarlar

Erol Asker Bu kişi benim

Fahrettin Filiz Bu kişi benim

Ece Uzkara Bu kişi benim

Orhan Zeybek Bu kişi benim

Yayımlanma Tarihi 1 Haziran 2012
Gönderilme Tarihi 1 Haziran 2012
Yayımlandığı Sayı Yıl 2012 Cilt: 14 Sayı: 1

Kaynak Göster

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. BAUN Fen. Bil. Enst. Dergisi. Haziran 2012;14(1):40-49.
Chicago Asker, Erol, Fahrettin Filiz, Ece Uzkara, ve Orhan Zeybek. “Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE Ve PKloranil Ile Yük-Transfer Kompleksleşmeleri”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 14, sy. 1 (Haziran 2012): 40-49.
EndNote Asker E, Filiz F, Uzkara E, Zeybek O (01 Haziran 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, ve O. Zeybek, “Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE ve PKloranil ile Yük-Transfer Kompleksleşmeleri”, BAUN Fen. Bil. Enst. Dergisi, c. 14, sy. 1, ss. 40–49, 2012.
ISNAD Asker, Erol vd. “Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE Ve PKloranil Ile Yük-Transfer Kompleksleşmeleri”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 14/1 (Haziran 2012), 40-49.
JAMA Asker E, Filiz F, Uzkara E, Zeybek O. Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE ve PKloranil ile Yük-Transfer Kompleksleşmeleri. BAUN Fen. Bil. Enst. Dergisi. 2012;14:40–49.
MLA Asker, Erol vd. “Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE Ve PKloranil Ile Yük-Transfer Kompleksleşmeleri”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, c. 14, sy. 1, 2012, ss. 40-49.
Vancouver Asker E, Filiz F, Uzkara E, Zeybek O. Karbazolun Yükseltgenmeli Kenetlenme Ürünlerinin TCNE ve PKloranil ile Yük-Transfer Kompleksleşmeleri. BAUN Fen. Bil. Enst. Dergisi. 2012;14(1):40-9.