β-Iminoenamine-BF 2 complexes: Aggregation-induced emission and pronounced effects of aliphatic rings on radiationless deactivation

Chemistry - An Asian Journal

Volumn 7, Issue 11, 2012, Pages 2670-2677

  Perumal, Karthikeyan ^b,c   Garg, Jai Anand ^a   Blacque, Olivier ^a   Saiganesh, Ramanathan ^b   Kabilan, Senthamaraikannan ^c   Balasubramanian, Kallupattu Kuppusamy ^b,d   Venkatesan, Koushik ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b Shasun Research Centre   (India)

^c ANNAMALAI UNIVERSITY   (India)

^d B S ABDUR RAHMAN CRESCENT INSTITUTE OF SCIENCE AND TECHNOLOGY   (India)

Author keywords

interactions; aggregation induced emission; boron; chromophores; luminescence

Indexed keywords

AGGREGATION-INDUCED EMISSIONS; ALIPHATIC RING; FLUORINE ATOMS; FRONTIER ORBITALS; HETEROCYCLES; INTRA-MOLECULAR CHARGE TRANSFER; PHOTOPHYSICAL; RADIATIONLESS DEACTIVATION; ROOM TEMPERATURE; SINGLE CRYSTAL XRD; STOKES SHIFT; TIME-DEPENDENT DFT;

CHARGE TRANSFER; CHROMOPHORES; FLUORINE; LUMINESCENCE; QUANTUM YIELD;

BORON;

EID: 84867470454     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201200477     Document Type: Article

References (60)

1. Y. L. Rao, S. N. Wang, Inorg. Chem. 2011, 50, 12263-12274
2. S. N. Wang, Coord. Chem. Rev. 2001, 215, 79-98
3. C. D. Entwistle, T. B. Marder, Angew. Chem. 2002, 114, 3051-3056
4. Angew. Chem. Int. Ed. 2002, 41, 2927-2931
5. C. D. Entwistle, T. B. Marder, Chem. Mater. 2004, 16, 4574-4585
6. A. Fukazawa, S. Yamaguchi, Chem. Asian J. 2009, 4, 1386-1400
7. W. E. Piers, S. C. Bourke, K. D. Conroy, Angew. Chem. 2005, 117, 5142-5163
8. Angew. Chem. Int. Ed. 2005, 44, 5016-5036
9. G. Zhang, J. Lu, S. Michal, C. L. Fraser, J. Am. Chem. Soc. 2010, 132, 2160-2162.
10. G. Ulrich, R. Ziessel, A. Harriman, Angew. Chem. 2008, 120, 1202-1219
11. Angew. Chem. Int. Ed. 2008, 47, 1184-1201
12. A. Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891-4932
13. K. Umezawa, Y. Nakamura, H. Makino, D. Citterio, K. Suzuki, J. Am. Chem. Soc. 2008, 130, 1550
14. A. Gorman, J. Killoran, C. O'Shea, T. Kenna, W. M. Gallagher, D. F. O'Shea, J. Am. Chem. Soc. 2004, 126, 10619-10631
15. J. Killoran, L. Allen, J. F. Gallagher, W. M. Gallagher, D. F. O'Shea, Chem. Commun. 2002, 1862-1863
16. R. Ziessel, G. Ulrich, A. Harriman, New J. Chem. 2007, 31, 496-501
17. A. C. Benniston, G. Copley, Phys. Chem. Chem. Phys. 2009, 11, 4124-4131
18. N. Boens, V. Leen, W. Dehaen, Chem. Soc. Rev. 2012, 41, 1130-1172
19. Q. Bellier, S. Pegaz, C. Aronica, B. Le Guennic, C. Andraud, O. Maury, Org. Lett. 2011, 13, 22-25.
20. T. Ozdemir, S. Atilgan, I. Kutuk, L. T. Yildirim, A. Tulek, M. Bayindir, E. U. Akkaya, Org. Lett. 2009, 11, 2105-2107.
21. B. Neue, R. Frohlich, B. Wibbeling, A. Fukazawa, A. Wakamiya, S. Yamaguchi, E. U. Wurthwein, J. Org. Chem. 2012, 77, 2176-2184
22. Y. Hayashi, N. Obata, M. Tamaru, S. Yamaguchi, Y. Matsuo, A. Saeki, S. Seki, Y. Kureishi, S. Saito, S. Yamaguchi, H. Shinokubo, Org. Lett. 2012, 14, 866-869
23. Y. Kubota, H. Hara, S. Tanaka, K. Funabiki, M. Matsui, Org. Lett. 2011, 13, 6544-6547
24. A. Job, A. Wakamiya, G. Kehr, G. Erker, S. Yamaguchi, Org. Lett. 2010, 12, 5470-5473
25. Z. Zhang, B. Xu, J. Su, L. Shen, Y. Xie, H. Tian, Angew. Chem. 2011, 123, 11858-11861
26. Angew. Chem. Int. Ed. 2011, 50, 11654-11657
27. M. Shimizu, R. Kaki, Y. Takeda, T. Hiyama, N. Nagai, H. Yamagishi, H. Furutani, Angew. Chem. 2012, 124, 4171-4175
28. Angew. Chem. Int. Ed. 2012, 51, 4095-4099.
29. Y. Rao, H. Amarne, S. Wang, Coord. Chem. Rev. 2012, 256, 759.
30. J. F. Araneda, W. E. Piers, B. Heyne, M. Parvez, R. McDonald, Angew. Chem. 2011, 123, 12422-12425
31. Angew. Chem. Int. Ed. 2011, 50, 12214-12217.
32. L. Bourget-Merle, M. F. Lappert, J. R. Severn, Chem. Rev. 2002, 102, 3031-3065.
33. F. P. Macedo, C. Gwengo, S. V. Lindeman, M. D. Smith, J. R. Gardinier, Eur. J. Inorg. Chem. 2008, 3200-3211.
34. X. M. Liu, W. Gao, Y. Mu, G. H. Li, L. Ye, H. Xia, Y. Ren, S. H. Feng, Organometallics 2005, 24, 1614-1619
35. X. M. Liu, H. Xia, W. Gao, L. Ye, Y. Mu, Q. Su, Y. Ren, Eur. J. Inorg. Chem. 2006, 1216-1222
36. Y. Ren, X. M. Liu, H. Xia, L. Ye, Y. Mu, Eur. J. Inorg. Chem. 2007, 1808-1814
37. Z. Li, Y. Dong, B. X. Mi, Y. H. Tang, M. Haussler, H. Tong, Y. P. Dong, J. W. Y. Lam, Y. Ren, H. H. Y. Sung, K. S. Wong, P. Gao, I. D. Williams, H. S. Kwok, B. Z. Tang, J. Phys. Chem. B 2005, 109, 10061-10066.
38. K. K. Balasubramanian, G. V. Bindumadhavan, M. Nair, B. Venugopalan, Synthesis 1977, 611-612
39. P. Karthikeyan, A. M. Rani, R. Saiganesh, K. K. Balasubramanian, S. Kabilan, Tetrahedron 2009, 65, 811-821
40. R. Saiganesh, K. K. Balasubramanian, Modern Approaches to the Synthesis of O- and N-Heterocycles, Research Signpost, 2007
41. K. S. Swaminathan, R. S. Ganesh, C. S. Venkatachalam, K. K. Balasubramanian, Tetrahedron Lett. 1983, 24, 3653-3656.
42. V. R. Thalladi, S. Brasselet, H. C. Weiss, D. Blaser, A. K. Katz, H. L. Carrell, R. Boese, J. Zyss, A. Nangia, G. R. Desiraju, J. Am. Chem. Soc. 1998, 120, 2563-2577.
43. Photoinduced Electron Transfer (Eds.:, M. A. Fox, M. Chanon,), Elsevier, Amsterdam, 1988.
44. H. Langhals, T. Potrawa, H. Noth, G. Linti, Angew. Chem. 1989, 101, 497-499
45. Angew. Chem. Int. Ed. Engl. 1989, 28, 478-480.
46. S. Saito, K. Nakakura, S. Yamaguchi, Angew. Chem. 2012, 124, 738-741
47. Angew. Chem. Int. Ed. 2012, 51, 714-717.
48. Y. Hong, J. W. Y. Lam, B. Z. Tang, Chem. Soc. Rev. 2011, 40, 5361-5368
49. Y. Yang, X. Su, C. N. Carroll, I. Aprahamian, Chem. Sci. 2012, 3, 610-613.
50. R. Czerwieniec, J. B. Yu, H. Yersin, Inorg. Chem. 2011, 50, 8293-8301.
51. J. Pommerehne, H. Vestweber, W. Guss, R. F. Mahrt, H. Bassler, M. Porsch, J. Daub, Adv. Mater. 1995, 7, 551-554.
52. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652
53. C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789
54. B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 1989, 157, 200-206.
55. Gaussian 03, revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Rob, 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, V. Bakken, 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, Inc., Wallingford, CT, 2003.
56. M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees, J. A. Pople, J. Chem. Phys. 1982, 77, 3654-3665
57. R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650-654
58. A. D. Mclean, G. S. Chandler, J. Chem. Phys. 1980, 72, 5639-5648.
59. V. Barone, M. Cossi, J. Phys. Chem. A 1998, 102, 1995-2001
60. M. Cossi, N. Rega, G. Scalmani, V. Barone, J. Comput. Chem. 2003, 24, 669-681.