Photoinduced electron and energy transfer in aryldihydropyridines

Journal of Organic Chemistry

Volumn 74, Issue 17, 2009, Pages 6615-6622

  Jimenez, Angel J ^a,b   Fagnoni, Maurizio ^a   Mella, Mariella ^a   Albini, Angelo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL GROUP; CHEMICAL EQUATIONS; DICARBOXYLATES; DIHYDROPYRIDINES; ELECTRON TRANSFER; ELECTRON TRANSFER PROCESS; ENERGY SINKS; FASTER RATES; FLUID SOLUTIONS; GLASSY MATRICES; LUMINESCENCE MEASUREMENTS; PHOTO-ACTIVATED; PHOTOINDUCED ELECTRONS; ROOM TEMPERATURE; TRIPLET ENERGY; VISCOUS MEDIUM;

CARBOXYLATION; CHROMOPHORES; ELECTRON TRANSITIONS; ENERGY TRANSFER; GLYCEROL; LIGHT EMISSION; PHOSPHORESCENCE;

ARGON;

ARYLDIHYDROPYRIDINE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; DIMETHYL 2,6 DIMETHYL 1,4 DIHYDROPYRIDINE 3,5 DICARBOXYLIC ACID DERIVATIVE; GLYCEROL; NITROPHENOL; PHENANTHRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOPHORE; ELECTRON TRANSPORT; ENERGY TRANSFER; FLUORESCENCE; LUMINESCENCE; NONHUMAN; PHOSPHORESCENCE; PHOTOACTIVATION; PHOTOINDUCED ELECTRON TRANSFER; REACTION ANALYSIS; ROOM TEMPERATURE; SYNTHESIS; VISCOSITY;

EID: 69549103474     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9010816     Document Type: Article

References (51)

1. Gust, D.; Moore, T. A. Science 1989, 244, 35.
2. Schanze, K. S.; Walters, K. A., Molecular and Supramolecular Photochemistry; Ramamurthy, V., Schanze, K. S., Eds.; M. Dekker: New York, 1998; Vol.2, p 75.
3. Gust, D.; Moore, T. A.; Moore, A. L. Chem. Commun. 2006, 1169.
4. Durrant, J. R.; Haque, S. A.; Palomares, E. Chem. Commun. 2006, 3279.
5. Lee, C. H.; Guo, J.; Chen, L. X.; Mandal, B. K. J. Org. Chem. 2008, 73, 8219.
6. Armaroli, N. Photochem. Photobiol. Sci. 2003, 2, 73.
7. Verhoeven, J. W.; van Ramesdonk, H. J.; Groeneveld, M. M.; Benniston, A. C.; Harriman, A. ChemPhysChem 2005, 6, 2251.
8. Fukuzumi, S. Pure Appl. Chem. 2007, 79, 981.
9. D'Souza, F.; Chitta, R.; Ohkubo, K.; Tasior, M.; Subbaiyan, N. K.; Zandler, M. E.; Rogacki, M. K.; Gryko, D. T.; Fukuzumi, S. J. Am. Chem. Soc. 2008, 130, 14263.
10. Jiménez, M. C.; Miranda, M. A.; Termos, R. Chem. Soc. Rev. 2005, 34, 783.
11. Gonzalez-Rodriguez, D.; Torres, T.; Herranz, M. A.; Echegoyen, L.; Carbonell, E.; Guldi, D. M. Chem. - Eur. J. 2008, 14, 7670.
12. Kawauchi, H.; Suzuki, S.; Kozaki, M.; Okada, K.; Islam, D. M. S.; Araki, Y.; Ito, O.; Yamanaka, K. J. Phys. Chem. A 2008, 112, 5878.
13. Nakamura, T.; Araki, Y.; Ito, O.; Takimiya, K.; Otsubo, T. J. Phys. Chem. A 2008, 112, 1125.
14. Fujitsuka, M.; Harada, K.; Sugimoto, A.; Majima, T. J. Phys. Chem. A 2008, 112, 10193.
15. Shibano, Y.; Umeyama, T.; Matano, Y.; Tkachenko, N. V.; Lemmetyinen, H.; Imahori, H. Org. Lett. 2006, 8, 4425.
16. Yongjun; Zheng, H.; Li, Y.; Wang, S.; Wu, Z.; Liu, P.; Gao, Z.; Liu, H.; Zhu, D. J. Org. Chem. 2007, 72, 2878.
17. Fasani, F.; Fagnoni, M.; Dondi, D.; Albini, A. J. Org. Chem. 2006, 71, 2037.
18. Yamaoka, T.; Yokoyama, S.; Omote, T.; Naitoh, K.; Yoshida, K. J. Photopolym. Sci. Technol. 1996, 51, 392.
19. Yamaoka, T.; Yokoyama, S.; Omote, T.; Naitoh, K. J. Polym. Sci. Technol. 1994, 7, 293.
20. Wang, H. W.; Gukassyan, V.; Chen, C. T.; Wei, Y. H.; Guo, H. W.; Yu, J. S.; Kao, F. J. J. Biomed. Opt. 2008, 13, 054011/1.
21. Ramanujan, V. K.; Jo, J. A.; Cantu, G.; Herman, B. A. J. Microsc. 2008, 230, 329.
22. Katz, E.; Heleg-Shabtai, V.; Bardea, A.; Willner, I.; Rau, H. K.; Haehnel, W. Biosens. Bioelectron. 1998, 13, 741.
23. Hantzsch, A. Liebigs Ann. 1882, 215 (1), 72.
24. Lavilla, R. J. Chem. Soc., Perkin Trans. 1 2002, 1141.
25. Triggle, A. M.; Shefter, E.; Triggle, G. J. Med. Chem. 1980, 23, 1442.
26. Fossheim, R.; Joslyn, A.; Solo, A. J.; Luchowski, E.; Rutlege, A.; Triggle, D. J. J. Med. Chem. 1988, 31, 300.
27. Wang, S. D.; Herbette, L. G.; Rhodes, D. G. Acta Crystallogr., Sect. C 1989, C45, 1748.
28. Palmer, R. B.; Andersen, N. H. Bioorg. Med. Chem. Lett. 1996, 6, 2173.
29. Kurfürst, A.; Kuthan, J. Collect. Czech., Chem. Commun. 1983, 43, 1422.
30. Deme, A. K.; Lusis, V. K.; Dubur, G. Y. Khim. Geterotsikl. Soedin. 1987, 67.
31. Pàvez, P.; Encinas, M. V. Photochem. Photobiol. 2007, 83, 722.
32. (a) Lin, Z. P.; Aue, W. A. Spectrochim. Acta, Part A 2000, 56, 111.
33. (b) Takezaki, M.; Hirota, N.; Terazima, M. J. Phys. Chem. A 1997, 101, 3443.
34. (c) Herkstroeter, W. G.; Farid, S. J. Photochem. 1986, 36, 71.
35. (d) Schweitzer, C.; Mehrdad, Z.; Noll, A.; Grabner, E. W.; Schmidt, R. J. Phys. Chem. A 2003, 107, 2192.
36. (e) Li, R.; Lim, E. C. J. Chem. Phys. 1972, 57, 605.
37. (f) Ishitani, O.; Yanagida, S.; Takamuku, S.; Pac, C. J. Org. Chem. 1987, 52, 2790.
38. (g) Yanagida, S.; Ogata, T.; Shindo, A.; Hosokawa, H.; Mori, H.; Sakata, T.; Wada, Y. Bull. Chem. Soc. Jpn. 1995, 68, 752.
39. (h) Bento, M. F.; Medeiros, M. J.; Montenegro, M. I.; Beriot, C.; Pletcher, D. J. Electroanal. Chem. 1993, 345, 273.
40. (i) Shibata, T.; Kabumoto, A.; Shiragami, T.; Ishitani, O.; Pac, C.; Yanagida, S. J. Phys. Chem. 1990, 94, 2068.
41. (j) Milne, P. H.; Wayner, D. D. M.; DeCosta, D. P.; Pincock, J. A. Can. J. Chem. 1992, 70, 121.
42. (k) Pedersen, S. U.; Lund, T.; Daasbjerg, K.; Pop, M.; Fussing, I.; Lund, H. Acta Chem. Scand. 1993, 47, 398.
43. (l) Lopez-Alarcon, C.; Squella, J. A.; Mirando-Wilson, D.; Nunez-Veregara, L. Electroanalysis 2004, 16, 539.
44. Albini, A.; Spreti, S. Tetrahedron 1984, 40, 2975.
45. Rampa, A.; Budriesi, R.; Bisi, A.; Valenti, P. Arzneim. Forsch. 1992, 42, 1284.
46. Guengerich, F. P.; Brian, W. R.; Iwasaki, M.; Sari, M. A.; Baeaernhielm, C.; Berntsson, P. J. Med. Chem. 1991, 34, 1838.
47. Ohsumi, K.; Ohishi, K.; Morinaga, Y.; Nakagawa, R.; Suga, Y.; Takashi, T.; Yukio, A.; Takashi, T. Chem. Pharm. Bull. 1995, 43, 818.
48. Gupta, A. K.; Song, C. H.; Oh, C. H. Tetrahedron Lett. 2004, 45, 4113.
49. Dewar, M. J. S.; Grisdale, P. J. J. Am. Chem. Soc. 1962, 84, 3541.
50. Treibs, W.; Beger, J. Liebigs Ann. Chem. 1962, 652, 192.
51. Bonesi, S. M.; Erra-Balsells, R. J. Lumin. 2001, 93, 51.