Synthesis and Properties of Alkyl Chain Substituted Naphthalenetetracarboxylic Monoanhydride Monoimides and Unsymmetrically Substituted Naphthalene Derivatives

Banu Koz; Serafettin Demic; Siddik Icli

doi:10.14233/ajchem.2016.20111

Issue

Vol. 28 No. 12 (2016): Vol 28 Issue 12

Issue Published : September 1, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Properties of Alkyl Chain Substituted Naphthalenetetracarboxylic Monoanhydride Monoimides and Unsymmetrically Substituted Naphthalene Derivatives

https://doi.org/10.14233/ajchem.2016.20111

Banu Koz

Department of Energy Systems Engineering, Faculty of Engineering, Karamanoglu Mehmetbey University, Karaman, Turkey

Serafettin Demic

Department of Material Science and Engineering, Faculty of Engineering, Izmir Katip Çelebi University, Izmir, Turkey

Siddik Icli

Solar Energy Institute, Ege University, Izmir, Turkey

Corresponding Author(s) : Banu Koz

banukoz@kmu.edu.tr

Asian Journal of Chemistry, Vol. 28 No. 12 (2016): Vol 28 Issue 12
Article Published : September 2, 2016

Abstract

1,4,5,8-Naphthalenedianhydride is converted to N-(2-ethylhexyl)-1,4,5,8-naphthalenetetracarboxylic monoanhydride monoimide (2a) and N-(2-hydroxyethyl)-1,4,5,8-naphthalenetetracarboxylic monoanhydride monoimide (2c) through the potassium salt prepared from a reaction with potassium hydroxide. N-Dodecyl-1,4,5,8-naphthalenetetracarboxylic monoanhydride monoimide (2b) was prepared by the condensation reaction of 1,4,5,8-naphthalenedianhydride with dodecylamine. Naphthalene-1,4-N-(2-ethylhexyl)-imide-N-ethyl-1H-benzo[d]imidazol-5-carboxylate and naphthalene-1,4-N-dodecyl-imide-N-ethyl-1H-benzo[d]imidazol-5-carboxylate were prepared by the condensation reaction of N-alkyl-1,4,5,8-naphthalenetetracarboxylic monoanhydride monoimide (alkyl = 2-ethylhexyl and dodecyl) with ethyl 3,4-diaminobenzoate. Molecular structures and electrochemical properties of all naphthalene derivatives were determined. Their thermal properties were also studied by thermal gravimetric analysis.

Keywords

Condensation reaction Monopotassium salt Monoanhydride monoimides

Koz, B., Demic, S., & Icli, S. (2016). Synthesis and Properties of Alkyl Chain Substituted Naphthalenetetracarboxylic Monoanhydride Monoimides and Unsymmetrically Substituted Naphthalene Derivatives. Asian Journal of Chemistry, 28(12), 2755–2758. https://doi.org/10.14233/ajchem.2016.20111

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References

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References

P. Peumans, A. Yakimov and S.R. Forrest, J. Appl. Phys., 93, 3693 (2003); doi:10.1063/1.1534621.

N. Peyghambarian and R.A. Norwood, Optics Photon. News, 16, 28 (2005); doi:10.1364/OPN.16.4.000028.

C.W. Tang, Appl. Phys. Lett., 48, 183 (1986); doi:10.1063/1.96937.

C.J. Brabec, N.S. Sariciftci and J.C. Hummelen, Adv. Funct. Mater., 11, 15 (2001); doi:10.1002/1616-3028(200102)11:1<15::AID-ADFM15>3.0.CO;2-A.

M.T. Bernius, M. Inbasekaran, J. O’Brien and W. Wu, Adv. Mater., 12, 1737 (2000); doi:10.1002/1521-4095(200012)12:23<1737::AID-ADMA1737>3.0.CO;2-N.

Y.Z. Wang, R.G. Sun, D.K. Wang, T.M. Swager and A. Epstein, Appl. Phys. Lett., 74, 2593 (1999); doi:10.1063/1.123952.

J. Rostalski and D. Meissner, Sol. Energy Mater. Sol. Cells, 61, 87 (2000); doi:10.1016/S0927-0248(99)00099-9.

M. Westphalen, U. Kreibig, J. Rostalski, H. Lüth and D. Meissner, Sol. Energy Mater. Sol. Cells, 61, 97 (2000); doi:10.1016/S0927-0248(99)00100-2.

K. Takahashi, N. Kuraya, T. Yamaguchi, T. Komura and K. Murata, Sol. Energy Mater. Sol. Cells, 61, 403 (2000); doi:10.1016/S0927-0248(99)00163-4.

M. Pfeiffer, A. Beyer, B. Plönnigs, A. Nollau, T. Fritzz, K. Leo, D. Schlettwein, S. Hiller and D. Wöhrle, Sol. Energy Mater. Sol. Cells, 63, 83 (2000); doi:10.1016/S0927-0248(00)00022-2.

M. Hoffmann, K. Schmidt, T. Fritz, T. Hasche, V.M. Agranovich and K. Leo, in eds.: F. Kajzar and V. Agranovich, Multiphoton and Light Driven Multielectron Processes: Materials, Phenomena, Applications, NATO Advanced Research Workshop, Kluwer Dordrecht, The Netherlands, p. 123 (2000).

R.H. Friend, M. Granström, K. Petritsch, A.C. Arias, A. Lux and M.R. Andersson, Nature, 395, 257 (1998); doi:10.1038/26183.

C.C. Leznoff, Phthalocyanines, Properties and Applications, VCH, New York (1989).

M. Hiramoto, H. Fujiwara and M. Yokoyama, Appl. Phys. Lett., 58, 1062 (1991); doi:10.1063/1.104423.

M. Hiramoto, H. Fukusumi and M. Yokoyama, Appl. Phys. Lett., 61, 2580 (1992); doi:10.1063/1.108133.

H. Tröster, Dyes Pigments, 4, 171 (1983); doi:10.1016/0143-7208(83)80015-1.

M.J. Fuller and M.R. Wasielewski, J. Phys. Chem. B, 105, 7216 (2001); doi:10.1021/jp011561v.

I. Yildiz-Oren, I. Yalcin, E. Aki-Sener and N. Ucarturk, Eur. J. Med. Chem., 39, 291 (2004); doi:10.1016/j.ejmech.2003.11.014.

H. Gilman, R. Adams, H.T. Clarke, J.B. Conant, C.S. Marvel, C.R. Noller and F.C. Whitmore, Organic Synthesis Collective, John Wiley & Sons, Inc, New York, edn 2, vol. 1, pp. 237–238 (1941).

H.M. Koepp, H. Wendt and H. Strehlow, Z. Elektrochem., 64, 483 (1960); doi:10.1002/bbpc.19600640406.

J.L. Bredas, R. Silbey, D.S. Boudreaux and R.R. Chance, J. Am. Chem. Soc., 105, 6555 (1983); doi:10.1021/ja00360a004.

D. Uzun, M.E. Ozser, K. Yuney, H. Icil and M. Demuth, J. Photochem. Photobiol. Chem., 156, 45 (2003); doi:10.1016/S1010-6030(02)00436-7.

S. Alp, Ş. Erten, C. Karapire, B. Köz, A.O. Doroshenko and S. Icli, J. Photochem. Photobiol. Chem., 135, 103 (2000); doi:10.1016/S1010-6030(00)00306-3.

Issue

Vol. 28 No. 12 (2016): Vol 28 Issue 12

Synthesis and Properties of Alkyl Chain Substituted Naphthalenetetracarboxylic Monoanhydride Monoimides and Unsymmetrically Substituted Naphthalene Derivatives

Corresponding Author(s) : Banu Koz

Abstract

Keywords

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