Browse > Article
http://dx.doi.org/10.5012/bkcs.2008.29.5.948

Photoinduced Charge-Transfer Association of Tetracyanoquinodimethane with Aminobiphenyls  

Kim, Yong-Hee (IT Convergence Research Laboratory, ETRI)
Jung, Sang-Don (IT Convergence Research Laboratory, ETRI)
Chung, Myung-Ae (IT Convergence Research Laboratory, ETRI)
Song, Ki-Dong (Department of Chemistry, Chosun University)
Cho, Dae-Won (Department of Chemistry, Chosun University)
Publication Information
Bulletin of the Korean Chemical Society / v.29, no.5, 2008 , pp. 948-952 More about this Journal
Abstract
The molecular association of acceptors with electron donors is studied in the highly-polar solvent $CH_3CN$. Tetracyanoquinodimethane (TCNQ) forms a stable charge-transfer complex with donor molecules such as 4- aminobiphenyl (4-AB), benzidine (BD) and 2-aminobiphenyl (2-AB) with high association constants. The complexes of TCNQ with 4-AB or BD show new absorption bands at around 800 and 500 nm, which can be identified as reduced $TCNQ^{{\bullet}-}$ and $TCNQ^{2-}$ species, respectively. These bands grow quickly upon photoirradiation, implying that the charge-transfer complexes are easily formed in an excited state. Conversely, a small spectral manifestation of the charge transfer was observed in the case of 2-AB complex. It is demonstrated that the structural orientation between the geminate ion pairs could play an important role in building a stable complex.
Keywords
Photoinduced electron transfer; 7,7',8,8'-Tetracyanoquinodimethane (TCNQ); 4-Aminobiphenyl; 2-Aminobiphenyl; Benzidine
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 5  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
1 Guillet, J. In Polymer Photophysics and Photochemistry: An Introduction to the Study of Photoprocesses in Macromolecules; Cambridge University Press: Cambridge, U.K. 1985
2 Coleman, L. B.; Cohen, J. A.; Garito, A. F.; Heeger, A. J. Phys. Rew. B 1973, 7, 2122   DOI
3 Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703   DOI
4 Rehm, D.; Weller, A. Isr. J. Chem. 1970, 259
5 Rehm, D.; Weller, A. Ber. Bunsenges. Phys. Chem.1969, 73, 837
6 Yamaguchi, S.; Potember, R. S. Synthetic Metals 1996, 78, 117   DOI   ScienceOn
7 Wheland, R. C.; Gillson, J. L. J. Am. Chem. Soc. 1976, 98, 3916   DOI   ScienceOn
8 Sein Jr, L. T.; Wei, Y.; Jansen, S. A. Synthetic Metals 2000, 108, 101   DOI   ScienceOn
9 Okamoto, K.; Ozeki, M.; Itaya, A.; Kusubayashi, S.; Mikawa, H. Bull. Chem. Soc. Jpn. 1975, 48, 1362   DOI
10 Pearson, J. M. Pure Appl. Chem. 1977, 49, 463   DOI
11 Ferraris, S. P.; Cowan, D.; Walalka, V.; Perlestein, J. H. J. Am. Chem. Soc. 1973, 95, 948   DOI
12 Kim, Y.-I.; Jeong, C.-K.; Lee, Y.-M.; Choi, S.-N. Bull. Korean Chem. Soc. 2002, 23, 1754   DOI   ScienceOn
13 Foster, R. Organic Charge Transfer Complexes; Academic Press: London, 1969
14 Cui, X. D.; Primak, A.; Zarate, X.; Tomfohr, J.; Sankey, O. F.;Moore, A. L.; Moore, T. A.; Gust, D.; Harris, G.; Lindsay, S. M. Science 2001, 294, 571   DOI   ScienceOn
15 Jeanmaire, D. L.; Van Duyne, R. P. J. Am. Chem. Soc. 1976, 98, 4029   DOI
16 Chen, S.-C.; Kao, C.-M.; Huang, M.-H.; Shih, M.-K.; Chen, Y.-L.; Huang, S.-P.; Liu, T.-Z. Toxicological Science 2003, 72, 283   DOI   ScienceOn
17 Sentchouk, V. V.; Grintsevich, E. E. Biochemistry (Moscow) 2004, 69, 201   DOI   ScienceOn
18 Kadlular, F. F.; Fu, P. P.; Jung, H.; Shaikh, A. U.; Beland, F. A. Environ. Health Perspect. 1990, 87, 233   DOI
19 Egan, H. Environmental Carcinogens-Selected Methods of Analysis in Some Aromatic Amines and Azo dyes in the General and Industrial Environment; IARC: Lyon, 1981; Vol. 4
20 Lai, D. Y.; Woo, Y. T.; Argus, M. F.; Arco, J. C. In Designing Safer Chemicals: Green Chemistry for Pollution Prevention, ACS Symposium Series 640; DeVito, S. C., Garrett, R. L., Eds.; American Chemical Society: Washington, D.C. 1996; pp 62-73
21 Jonkman, H. T.; Kommandeur, J. Chem. Phys. Lett. 1972, 15, 496   DOI   ScienceOn
22 Mulliken, R. S.; Person, W. B. Molecular Complexes; Wiley: New York, 1969
23 Verhoeven, J. W. Pure Appl. Chem. 1990, 62, 1585   DOI
24 De Schryver, F. C.; Declercq, D.; Depaemelaere, S.; Hermans, E.; Onkelinx, A.; Verhoeven, J. W.; Gelan, J. J. Photochem. Photobiol. A; Chem. 1994, 82, 171   DOI   ScienceOn
25 Schon, J. H.; Meng, H.; Bao, Z. Nature 2001, 413, 713   DOI   ScienceOn
26 Metzger, R. M. Acc. Chem. Res. 1999, 32, 950   DOI   ScienceOn
27 Goes, M.; Verhoeven, J. W.; Hofstraat, H.; Brunner, K. Chem. Phys. Chem. 2003, 4, 349   DOI   ScienceOn
28 Wooster, T. T.; Watanabe, M.; Murray, R. W. J. Phys. Chem. 1992, 96, 5886   DOI