Synthesis and quantum chemical study of PDI derivatives with phenylalkynyl groups at the bay position

Journal of Molecular Structure

Volumn 938, Issue 1-3, 2009, Pages 245-253

  Wang, Delou ^a   shi, Yan ^a   Zhao, Chuntao ^a   Liang, Baolong ^a   Li, Xiyou ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Absorption spectra; Fluorescence spectra; PDI; Phenylalkynyl; TD DFT

Indexed keywords

ABSORPTION AND EMISSION SPECTRA; ALKYNYLS; B3LYP/6-31G; CONJUGATION SYSTEM; DFT METHOD; ELECTRON TRANSFER; EMISSION PEAKS; FLUORESCENCE SPECTRA; FRONTIER MOLECULAR ORBITALS; PERYLENETETRACARBOXYLIC DIIMIDES; QUANTUM CALCULATION; QUANTUM CHEMICAL STUDIES; RED SHIFT; SIDE CHAINS; SIMULATED RESULTS; UV-VIS ABSORPTIONS;

EMISSION SPECTROSCOPY; FLUORESCENCE; FLUORINE CONTAINING POLYMERS; LIGHT ABSORPTION; MOLECULAR ORBITALS; ORGANIC POLYMERS; PROBABILITY DENSITY FUNCTION; SYNTHESIS (CHEMICAL);

ABSORPTION;

EID: 70449624795     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2009.09.035     Document Type: Article

References (37)

1. Katz H.E., Bao Z., and Gilat S.L. Acc. Chem. Res. 34 (2001) 359-369
2. Würthner F. Angew. Chem. Int. ED. 40 (2001) 1037-1039
3. Angadi M.A., Gosztola D., and Wasielewski M.R. Mater. Sci. Eng. B 63 (1999) 191-194
4. Ranke P., Bleyl I., Simmerer J., Haarer D., Bacher A., and Schmidt H.W. Appl. Phys. Lett. 71 (1997) 1332-1334
5. Law K.Y. Chem. Rev. 93 (1993) 449-486
6. Gregg B.A., and Cormier R.A. J. Am. Chem. Soc. 123 (2001) 7959-7960
7. Breeze A.J., Salomon A., Ginley D.S., Gregg B.A., Tillmann H., and Horhold H.H. Appl. Phys. Lett. 81 (2002) 3085-3087
8. Hayes R.T., Wasielewski M.R., and Gosztola D. J. Am. Chem. Soc. 122 (2000) 5563-5567
9. Davis W.B., Svec W.A., Ratner M.A., and Wasielewski M.R. Nature 396 (1998) 60-63
10. Hippiu F., and Schlosser F. J. Am. Chem. Soc. 128 (2006) 3870-3871
11. Tornizaki K., Loewe R.S.R.S., Kirmaier C., Schwartz J.K., Retsek J.L., and Bocian D.F. J. Org. Chem. 67 (2002) 6519-6531
12. Hagfeldt A., and Gratzel M. Acc. Chem. Res. 33 (2000) 269-277
13. Balakrishman K., Datar A., Naddo T., Huang J., Oitker R., Yen M., Zhao J., and Zhang L. J. Am. Chem. Soc. 128 (2006) 7390-7398
14. Balakrishnan K., Datar A., Oitker R., Chen H., Zuo J., and Zang L. J. Am. Chem. Soc. 127 (2005) 10496-10497
15. Locklin J., Li D., Mannsfeld S.C.B., Borken E., Meng H., Advincula R., and Bao Z. Chem. Mater. 17 (2005) 3366-3374
16. Chen Z., Debije M.G., Debaerdemaeker T., Osswald P., and Würthner F. Chemphychem 5 (2004) 137-140
17. Chao C.C., Leung M.K., Su Y.O., Chiu K.Y., Liu T.H., Shieh S.J., and Lin S.C. J. Org. Chem. 70 (2005) 4323-4331
18. Becker S., Böhm A., and Müllen K. J. Chem. Eur. 6 (2000) 3984-3990
19. Langhals H., and Blanke P. Dyes Pigment 59 (2003) 109-116
20. Sandrai M., Hadel L., Sauers R.R., Husain S., and Krogh-Jespersen K. J. Phys. Chem. 96 (1992) 7988-7996
21. Ego C., Marsitzkey D., Becker S., Zhang J., Grimsdale A.C., MacKenzie J.D., Silva C., and Friend R.H. J. Am. Chem. Soc. 125 (2003) 437-443
22. Qiu W., Chen S., Sun X., Liu Y., and Zhu D. Org. Lett. 8 (2006) 867-870
23. Serin J.M., Brousmiche D.W., and Frechet J.M.J. J. Am. Chem. Soc. 124 (2002) 11848-11849
24. Giaimo J.M., Gusev A.V., and Wasielewski M.R. J. Am. Chem. Soc. 124 (2002) 8530-8531
25. Jones B.A., Ahrens M.J., Yoon M.H., Facchetti A., Marks T.J., and Wasielewski M.R. Angew. Chem. Int. Ed. 43 (2004) 6363-6366
26. Ahrens M.J., Fuller M.J., and Wasilewski M.R. Chem. Mater. 15 (2003) 2684-2686
27. Zhao C., Zhang Y., Li R., Li R., and Jiang J. J. Org. Chem. 72 (2007) 2402-2410
28. Raramasivan R., Revital C., Elijah S., Linda J.W., and Boris R. J. Org. Chem. 72 (2007) 5973-5979
29. Hadicke F., and Graser F. Acta Crystallogr. Sect. C 42 (1986) 189-195
30. Su W., Zhang Y., Zhao C., Li X., and Jiang J. ChemPhysChem 8 (2007) 1857-1862
31. Dreuw A., and Head-Gordon M. Chem. Rev. 105 (2005) 4009-4037
32. Dreuw A., and Head-Gordon M. J. Am. Chem. Soc. 126 (2004) 4007-4016
33. Wang Y., and Wu G. Acta Phys. Chim. Sin. 23 (2007) 1813-1818
34. Wang Y., and Wu G. Acta Phys. Chim. Sin. 24 (2008) 552-560
35. Ahrens M.J., Sinks L.E., Rybtchinski B., Liu W., Jones B.A., Giaimo J.M., Gusev A.V., Goshe A.J., Tiede D.M., and Wasielewski M.R. J. Am. Chem. Soc. 126 (2004) 8284-8294
36. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M. W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision B.05, Gaussian, Inc., Pittsburgh, PA, 2003.
37. S.I. Gorelsky, SWizard program. http://www.sg-chem.net/.