Nature of the intense near-IR absorption and unusual broad UV-visible-NIR spectra of azulenocyanines: Density functional theory studies

Journal of Physical Chemistry A

Volumn 114, Issue 51, 2010, Pages 13411-13417

  Qi, Dongdong ^a   Zhang, Lijuan ^a   Zhang, Yuexing ^a   Bian, Yongzhong ^a   Jiang, Jianzhuang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY BEIJING   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION BAND; AZULENES; CONJUGATED SYSTEMS; ELECTRON-DONATING SUBSTITUENTS; ELECTRONWITHDRAWING; HIGHEST OCCUPIED MOLECULAR ORBITAL; LOWEST UNOCCUPIED MOLECULAR ORBITAL; NAPHTHALOCYANINES; NEAR-IR; NEAR-IR ABSORPTION; NIR SPECTRUM; RED-SHIFTED; SMALL GAPS; SORET BANDS; TIME-DEPENDENT DFT; UV-VISIBLE;

ABSORPTION; ELECTRON TRANSITIONS; INFRARED DEVICES; ISOMERS; MOLECULAR MODELING; MOLECULAR ORBITALS;

DENSITY FUNCTIONAL THEORY;

AZULENE DERIVATIVE; CARBOCYANINE; COLORING AGENT;

ALGORITHM; ARTICLE; CHEMISTRY; ELECTRON TRANSPORT; ISOMERISM; METHODOLOGY; NEAR INFRARED SPECTROSCOPY; QUANTUM THEORY; TIME; ULTRAVIOLET SPECTROPHOTOMETRY;

ALGORITHMS; AZULENES; CARBOCYANINES; COLORING AGENTS; ELECTRON TRANSPORT; ISOMERISM; QUANTUM THEORY; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, NEAR-INFRARED; TIME FACTORS;

EID: 78650606983     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp109256k     Document Type: Article

References (37)

1. Tsuda, A.; Osuka, A. Science 2001, 293, 79-82
2. Peumans, P.; Yakimov, A.; Forrest, S. R. J. Appl. Phys. 2003, 93, 3693-3723
3. Hiramoto, M.; Fujiwara, H.; Yokoyama, M. J. Appl. Phys. 1992, 72, 3781-3787
4. Allen, C. M.; Sharman, W. M.; Van Lier, J. E. J. Porphyrins Phthalocyanines 2001, 5, 161-169
5. Detty, M. R.; Gibson, S. L.; Wagner, S. J. J. Med. Chem. 2004, 47, 3897-3915
6. Fabian, J.; Nakazumi, H.; Matsuoka, M. Chem. Rev. 1992, 92, 1197-1226
7. Matsuoka, M. Infrared Absorbing Dyes; Plenum Press: New York, 1990.
8. Weissleder, R. Nat. Biotechnol. 2001, 19, 316-317
9. de la Torre, G.; Claessen, C. G.; Torres, T. Chem. Commun. 2007, 2000-2015
10. Rihter, B. D.; Kenney, M. E.; Ford, W. E.; Rodgers, M. A. J. J. Am. Chem. Soc. 1993, 115, 8146-8152
11. Muranaka, A.; Yonehara, M.; Uchiyama, M. J. Am. Chem. Soc. 2010, 132, 7844-7845
12. Imahori, H.; Umeyama, T.; Ito, S. Acc. Chem. Res. 2009, 42, 1809-1818
13. Ito, F.; Inoue, T.; Tomita, D.; Nagamura, T. J. Phys. Chem. B 2009, 113, 5458-5463
14. Yan, S.; Bu, Y.; Cao, Z.; Li, P. J. Phys. Chem. A 2004, 108, 7038-7049
15. Qi, D.; Zhang, Y.; Zhang, L.; Jiang, J. J. Phys. Chem. A 2010, 114, 1931-1938
16. Zhang, Y.; Cai, X.; Yao, P.; Xu, H.; Bian, Y.; Jiang, J. Chem. - Eur. J. 2007, 13, 9503-9514
17. Nemykin, V. N.; Hadt, R. G.; Belosludov, R. V.; Mizuseki, H.; Kawazoe, Y. J. Phys. Chem. A 2007, 111, 12901-12913
18. Lee, S. U.; Kim, J. C.; Mizuseki, H.; Kawazoe, Y. Chem. Asian J. 2010, 5, 1341-1346
19. Peralta, G. A.; Seth, M.; Zhekova, H.; Ziegler, T. Inorg. Chem. 2008, 47, 4185-4198
20. Donzello, M. P.; Ercolani, C.; Kadish, K. M.; Ricciardi, G.; Rosa, A.; Stuzhin, P. A. Inorg. Chem. 2007, 46, 4145-4157
21. Cai, X.; Zhang, Y.; Qi, D.; Jiang, J. J. Phys. Chem. A 2009, 113, 2500-2506
22. Zhang, Y.; Cai, X.; Zhou, Y.; Zhang, X.; Xu, H.; Liu, Z.; Li, X.; Jiang, J. J. Phys. Chem. A 2007, 111, 392-400
23. Zhang, Y.; Zhang, X.; Liu, Z.; Bian, Y.; Jiang, J. J. Phys. Chem. A 2005, 109, 6363-6370
24. Zhong, A.; Bian, Y.; Zhang, Y. J. Phys. Chem. C 2010, 114, 3248-3255
25. Zhang, Y.; Cai, X.; Qi, D.; Bian, Y.; Jiang, J. J. Phys. Chem. C 2008, 112, 14579-14588
26. Qi, D.; Zhang, Y.; Cai, X.; Jiang, J.; Bai, M. J. Mol. Graphics Modell. 2009, 27, 693-700
27. Wan, L.; Zhang, Y.; Qi, D.; Jiang, J. J. Mol. Graphics Modell. 2010, 28, 842-851
28. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
29. Lee, C.; Yang, W. R.; Parr, G. Phys. Rev. 1988, B37, 785-792
30. Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49-56
31. Becke, D. Phys. Rev. A 1988, 38, 3098-3100
32. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824
33. Gorelsky, S. I. SWizard Program; University of Ottawa: Ottawa, Canada, 2010; http://www.sg-chem.net/.
34. Gorelsky, S. I.; Lever, A. B. P. J. Organomet. Chem. 2001, 635, 187-196
35. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
36. Mack, J.; Stillman, M. J. The Porphyrin Handbook; Vol. 16, Chapter 103, pp 43 - 116.
37. Kobayashi, N.; Mack, J.; Ishii, K.; Stillman, M. J. Inorg. Chem. 2002, 21, 5350-5363