Intramolecular charge transfer in 5-methoxy-2-(2-pyridyl)thiazole-derived fluorescent molecules with different acceptor or donor substituents

Journal of Physical Chemistry A

Volumn 113, Issue 30, 2009, Pages 8635-8646

  Sun, Wei ^a   Zhou, Can ^a   Xu, Chun Hu ^a   Zhang, Yi Qun ^a   Li, Zhan Xian ^a   Fang, Chen Jie ^a   Sun, Ling Dong ^a   Yan, Chun Hua ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BATHOCHROMIC SHIFT; EMISSION PROPERTIES; EXCITED-STATE GEOMETRIES; FLUORESCENCE LIFETIMES; FLUORESCENCE SPECTRA; FLUORESCENT MOLECULES; HYDROXYL GROUPS; INTERCONVERSION; INTRA-MOLECULAR CHARGE TRANSFER; LOCAL INTERACTIONS; LOW TEMPERATURES; METHOXY; METHYL GROUP; NEW SERIES; POLAR SOLVENTS; PYRIDINE RINGS; PYRIDYL; ROOM TEMPERATURE; STEADY-STATE FLUORESCENCE; SYSTEMATIC INVESTIGATIONS; THEORETICAL CALCULATIONS; TRIPLE BONDS;

AMINES; CHARGE TRANSFER; EMISSION SPECTROSCOPY; EXCITED STATES; HYDROCARBONS; ION EXCHANGE; MASS TRANSFER; MOLECULES; PLASMA JETS; SULFUR COMPOUNDS;

FLUORESCENCE;

5 METHOXY 2 (2 PYRIDYL)THIAZOLE; 5-METHOXY-2-(2-PYRIDYL)THIAZOLE; PYRIDINE DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; QUANTUM THEORY; SPECTROFLUOROMETRY; SYNTHESIS;

FLUORESCENCE; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIDINES; QUANTUM THEORY; SPECTROMETRY, FLUORESCENCE; THIAZOLES;

EID: 67651177607     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9007224     Document Type: Article

References (57)

1. (a) de Silva, A. P.; Gunnlaugsson, H. Q. N.; McCoy. C. P. Nature 1993, 364, 42-44.
2. (b) de Silva, A. P.; McClenaghan, N. D.; McCoy, C. P. Molecular-Level Electronics, Imaging and Information, Energy and Environment. In Electron Transfer in Chemistry: Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany. 2001; Vol. 5.
3. (c) Balzani, V.; Venturi, M.; Credi, A. Molecular Devices and Machines A Journey into the Nano World: Wiley-VCH; Weinheim, Germany, 2003.
4. (d) de Silva, A. P. Nat. Mater. 2005, 4, 15-16.
5. (e) de Silva, A. P.; Uchiyama, S. Nat. Nanotechnol. 2007, 2, 399-410.
6. (f) Ballardin, R.; Ceroni, P.; Credi, A.; Gandolfi, M. T.; Maestri, M.; Semararo, M.; Venturi, M.; Balzani, V. Adv. Fund. Mater. 2007, 17, 740-750.
7. (g) Balzani, V.; Credi, A.; Venturi, M. Chem.-Eur. J. 2008, 14, 26-39.
8. (a) Brown, G. J.; de Silva, A. P.; Pagliari, S. Chem. Commun. 2002, 2461-2463.
9. (b) de Silva, A. P.; McClenaghan, N. D. Chem.-Eur. J. 2002, 8, 4935-4945.
10. (c) Raymo, F. M.; Giordani, S. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4941-2944.
11. (d) de Silva, A. P.; McCaughan, B.; McKinney, B. O. F.; Querol, M. Dalton Trans. 2003, 1902-1913.
12. (e) de Silva, A. P.; McClenaghan, N. D. Chem.-Eur. J. 2004, 10, 574-586.
13. (f) Guo, X. F.; Zhang, D. Q.; Zhu, D. B. Adv. Mater. 2004, 16, 125-130.
14. (g) Qu, D. H.; Ji, F. Y.; Wang, Q. C.; Tian, H. Adv. Mater. 2006, 18, 2035-2038.
15. (h) Zhou, W. D.; Li, Y. J.; Li, Y. L.; Liu, H. B.; Wang, S.; Li, C. H.; Yuan, M. J.; Liu, X. F.; Zhu, D. B. Chem. Asian J. 2006, 1-2, 224-230.
16. (a) Gust, D.; Moore, T. A.; Moore, A. L. Chem. Commun. 2006, 1169-1178.
17. (b) Biancardo, M.; Bignozzi, C.; Doyle, H.; Redmond, G. Chem. Cammun. 2005, 3918-3920.
18. (c) Raymo, F. M.; fomasulo. M. J. Phys. Chem. A 2005, 109, 7343-7352.
19. (d) Li. f. Y.; Shi, M.; Huang, C. H.; Jin, L. P. J. Mater. Chem. 2005, 15, 3015-3020.
20. (e) Zhou, Y.; Wu, H.; Qu, L.; Zhang, D. Q.; Zhu, D. B. J. Phys. Chem. B 2006, 110, 15676-15679.
21. (a) Balzani, V.; Credi, A.; Venturi, M. Chem Phys Chem 2003, 3, 49-59.
22. (b) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566.
23. Irie, M.; Fukaminato, T.; Saski, T.; Tamai, N.; Kawai, T. Nature 2002, 420, 759-760.
24. (a) Kollmannsberger, M.; Rurack, K.; Resch-Genger, U.; Daub, J. J. Phys. Chem. A 1998, 102, 10211-10220.
25. (b) Coskun, A.; Deniz, E.; Akkaya, E. U. Org. Lett. 2005, 7, 5187-5189.
26. (c) Xue, H.; Tang, X. J.; Wu, L. Z.; Zhang, L. P.; Tung, C. H. J. Org. Chem. 2005, 70, 9727-9734.
27. (d) García-Acosta, B.; Martínez-Máñez, R.; Sancenón, F.; Soto, J.; Rurack, K.; Spieles, M.; Garcia-Breijo, E.; Gil, L. Inorg. Chem. 2007, 46, 3123-3135.
28. (a) Valeur B. Molecular Fluorescence: Principles and Applications: Wiley-VCH: Weinheim, Germany, 2002.
29. (b) Suzuki, K.; Tanabe, H.; Tobita, S.; Shizuka, H. J. Phys. Chem. A 1997, 101, 4496-4503.
30. (c) Grabowski, Z. R.; Rotkiewicz, K.; Rettig, W. Chem. Rev. 2003, 103, 3899-4031.
31. (d) Nad, S.; Kumbhakar, M.; Pal, H. J. Phys. Chem. A 2003, 107, 4808-4816.
32. (e) El-Gezawy, H.; Rettig, W.; Lapouyade, R. J. Phys. Chem. A 2006, 110, 67-75.
33. (f) Resch-Genger, U.; Li, Y. Q.; Bricks, J. L.; Kharlanov, V.; Rettig, W. J. Phys. Chem. A 2006, 110, 10956-10971.
34. Zheng, M. H.; Jin, J. Y.; Sun, W.; Yan, C. H. New J. Chem. 2006, 30, 1192-1196.
35. (a) Fang, C. J.; Zhu, Z.; Sun, W.; Xu, C. H.; Yan, C. H. New J. Chem. 2007, 31, 580-586.
36. (b) Sun, W.; Zheng, Y. R.; Xu, C. H.; Fang, C. J.; Yan, C. H. J. Phys. Chem. C 2007, 111, 11706-11711.
37. (c) Li, Z. X.; Liao, L. Y.; Sun, W.; Xu, C. H.; Zhang, C.; Fang, C. J.; Yan, C. H. J. Phys. Chem. C 2008, 112, 5190-5196.
38. (d) Sun, W.; Zhou, C.; Xu, C. H.; Fang, C. J.; Zhang, C.; Li, Z. X.; Yan, C. H. Chem.-Eur. J. 2008, 14, 6342-6351.
39. (e) Sun, W.; Xu, C. H.; Zhu, Z.; Fang, C. J.; Yan, C. H. J. Phys. Chem. C 2008, 112, 16973-16983.
40. Demas, J. N.; Grosby, G. A. J. Phys. Chem. 1971, 75, 991-1024.
41. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; lyengar, 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.; 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. J.; Foresman, 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. G.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. GAUSSIAN 03, revision B.05; Gaussian, Inc.; Pittsburgh, PA, 2003.
42. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
43. (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
44. (d) Wadt, W. R.; Hay, P. J. Chem. Phys. 1985, 82, 284-298.
45. (e) Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B 1988, 37, 785-789.
46. (f) Adamo, C.; Barone, V. Chem. Phys. Lett. 2000, 330, 152-160.
47. (g) Jodicke, C. J.; Luthi, H. P. J. Chem. Phys. 2002, 117, 4146-4156.
48. (h) Scholz, R.; Kobitski, A. Y.; Zahn, D. R. T.; Schreiber, M. Phys. Rev. B 2005, 72, 245208-245225.
49. (i) Neiss, C.; Saalfrank, P.; Parac, M.; Grimme, S. J. Phys. Chem. A 2003, 107, 140-147.
50. Jia, C. Y.; Liu, S. X.; Tanner, C.; Leiggener, C.; Neels, A.; Sanguinet, L.; Levillain, E.; Leutwyler, S.; Hauser, A.; Decurtins, S. Chem-Eur. J. 2007, 13, 3804-3812.
51. Maus, M.; Rettig, W.; Bonafoux, D.; Lapouyade, R. J. Phys. Chem. A 1999, 103, 3388-3401.
52. Chakraborty, A.; Kar, S.; Nath, D. N.; Guchhait, N. J. Phys. Chem. A 2006, 110, 12089-12095.
53. (a) Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1956, 29, 465-470.
54. (b) El-Gezawy, H.; Rettig, W.; Lapouyade, R. J. Phys. Chem. A 2006, 110, 67-75.
55. Yang, J. S.; Liao, K. L.; Hwang, C. Y.; Wang, C. M. J. Phys. Chem. A 2006, 110, 8003-8010.
56. The emission wavelengths measured at low temperature are different from those measured at room temperature, even in the fluid solution. This may due to the differences in instrument apparatus. For measuring low-temperature fluorescence spectra, a Jobin-Yvon HR800 Raman spectrometer (France) with a 325 nm laser excitation source was used, whereas for measuring room-temperature fluorescence spectra, a Hitachi F4500 spectrometer is used. However, the trends of the changes in emission wavelength are still clear. For MPTEP, MPTET, MPTEO, and MPTEA, their emission wavelength maxima are red shifted upon the solution phase transition from liquid state to solid state upon being frozen. For MPTE, the same red shift cannot be observed. When the solution is frozen, the cooling speed is important for the emission maxima. If the cooling speed is fast, then some molecules will be frozen in their original conformation in fluid solvent, which still emits at shorter wavelength. This is the reason that MPTEO emits two peaks in the frozen dichloromethane solution at 120 K. However, in most cases, we do not observe the dual emission behavior seen in MPTEO.
57. Stsiapura, V. I.; Maskevich, A. A.; Kuzmitsky, V. A.; Turoverov, K. K.; Kuznetsova, 1. M. J. Phys. Chem. A 2007, 111, 4929-4835.