Control of circularly polarized photoluminescent property via dihedral angle of binaphthyl derivatives

Tetrahedron

Volumn 68, Issue 24, 2012, Pages 4791-4796

  Kinuta, Takafumi ^a   Tajima, Nobuo ^b   Fujiki, Michiya ^c   Miyazawa, Mitsuo ^a   Imai, Yoshitane ^a  

^a KINKI UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

^c NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Binaphthyl; Chiral; Circular dichroism (CD); Circularly polarized luminescence (CPL); Fluorescence

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; PHOTOLUMINESCENCE; PRIORITY JOURNAL; SPECTROSCOPY;

EID: 84861223227     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.119     Document Type: Article

References (49)

1. S.R. Forrest Chem. Rev. 97 1997 1793 1896
2. M. Glasbeek, and H. Zhang Chem. Rev. 104 2004 1929 1954
3. A. Mishra, R.K. Behera, P.K. Behera, B.K. Mishra, and G.B. Behera Chem. Rev. 100 2000 1973 2011
4. T. Baumgartner, and R. Reau Chem. Rev. 106 2006 4681 4727
5. P.G. Coble Chem. Rev. 107 2007 402 418
6. T.P.I. Saragi, T. Spehr, A. Siebert, T. Fuhrmann-Lieker, and J. Salbeck Chem. Rev. 107 2007 1011 1065
7. S.C. Lo, and P.L. Burn Chem. Rev. 107 2007 1097 1116
8. K. Walzer, B. Maennig, M. Pfeiffer, and K. Leo Chem. Rev. 107 2007 1233 1271
9. J. Grate Chem. Rev. 108 2008 726 745
10. F. Jakle Chem. Rev. 110 2010 3985 4022
11. V.K. Rai, R. Srivastava, and M.N. Kamalasanan J. Lumin. 130 2010 249 253
12. J. Huang, B. Xu, M.K. Lam, K.W. Cheah, H.C. Chen, and J.H. Su Dyes Pigments 89 2011 155 161
13. V.M. Agranovich, Yu.N. Gartstein, and M. Litinskaya Chem. Rev. 111 2011 5179 5214
14. J.E. Kwon, and S.Y. Park Adv. Mater 23 2011 3615 3642
15. T.H. Tran-Thi, R. Dagnelie, S. Crunaireza, and L. Nicole Chem. Soc. Rev. 40 2011 621 639 and references cited therein
16. J. Kido, and Y. Okamoto Chem. Rev. 102 2002 2357 2368
17. J. Yuan, and G. Wang J. Fluoresc. 15 2005 559 568
18. G.N. Zbancioc, T. Huhn, U. Groth, C. Deleanu, and I.I. Mangalagiu Tetrahedron 66 2010 4298 4306
19. N. Yongpruksa, S. Pandey, G.-A. Baker, and M. Harmata Org. Biomol. Chem. 9 2011 7979 7982
20. S. Karuppannan, and J.C. Chambron Chem. Asian J. 6 2011 964 984
21. C. Huang, S. Barlow, and S.R. Marder J. Org. Chem. 76 2011 2386 2407
22. M.B. Teimouri Tetrahedron 67 2011 1837 1843 and references cited therein
23. P.M.L. Blok, and H.P.J.M. Dekkers Chem. Phys. Lett. 161 1989 188 194
24. H.G. Brmtain Chirality 8 1996 357 363
25. K.E.S. Phillips, T.J. Katz, S. Jockusch, A.J. Lovinger, and N.J. Turro J. Am. Chem. Soc. 123 2001 11899 11907
26. J.E. Field, G. Muller, J.P. Riehl, and D. Venkataraman J. Am. Chem. Soc. 125 2003 11808 11809
27. T. Kawai, K. Kawamura, H. Tsumatori, M. Ishikawa, M. Naito, M. Fujiki, and T. Nakashima ChemPhysChem 8 2007 1465 1468
28. M. Seitz, E.G. Moore, A.J. Ingram, G. Muller, and K.N. Raymond J. Am. Chem. Soc. 129 2007 15468 15470
29. S. Haraguchi, M. Numata, C. Li, Y. Nakano, M. Fujiki, and S. Shinkai Chem. Lett. 38 2009 254 255
30. Y. Kawagoe, M. Fujiki, and Y. Nakano New J. Chem. 34 2010 637 647
31. H. Tsumatori, T. Nakashima, and T. Kawai Org. Lett. 12 2010 2362 2365
32. M. Pecul, and K. Ruud Phys. Chem. Chem. Phys. 13 2011 643 650
33. H. Maeda, Y. Bando, K. Shimomura, I. Yamada, M. Naito, K. Nobusawa, H. Tsumatori, and T. Kawai J. Am. Chem. Soc. 133 2011 9266 9269
34. R. Tempelaar, A. Stradomska, J. Knoester, and F.C. Spano J. Phys. Chem. B 115 2011 10592 10603
35. Y. Nakano, and M. Fujiki Macromolecules 44 2011 7511 7519 and references cited therein
36. Y. Imai, K. Kawano, Y. Nakano, K. Kawaguchi, T. Harada, T. Sato, M. Fujiki, R. Kuroda, and Y. Matsubara New J. Chem. 32 2008 1110 1112
37. N. Nishiguchi, T. Kinuta, Y. Nakano, T. Harada, N. Tajima, T. Sato, M. Fujiki, R. Kuroda, Y. Matsubara, and Y. Imai Chem. Asian J. 6 2011 1092 1098
38. N. Nishiguchi, T. Kinuta, T. Sato, Y. Nakano, H. Tokutome, N. Tajima, M. Fujiki, R. Kuroda, Y. Matsubara, and Y. Imai Chem. Asian J. 7 2012 360 366
39. I. Hanazaki, and H. Akimoto J. Am. Chem. Soc. 94 1972 4102 4106
40. S.F. Mason, and R.H. Seal Tetrahedron 30 1974 1671 1682
41. K. Takaishi, M. Kawamoto, K. Tsubaki, and T. Wada J. Org. Chem. 74 2009 5723 5726
42. K. Takaishi, A. Muranaka, M. Kawamoto, and M. Uchiyama J. Org. Chem. 76 2011 7623 7628
43. M. Nishizaka, T. Mori, and Y. Inoue J. Phys. Chem. A 115 2011 5488 5495
44. K. Takaishi, A. Muranaka, M. Kawamoto, and M. Uchiyama Org. Lett. 14 2012 276 279
45. T. Kinuta, T. Sato, Y. Nakano, T. Harada, N. Tajima, M. Fujiki, R. Kuroda, Y. Matsubara, and Y. Imai J. Photochem. Photobiol., A: Chem. 2011 134 138
46. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
47. T.H. Dunning Jr. J. Chem. Phys. 90 1989 1007 1023
48. J. Tomasi, B. Mennucci, and R. Cammi Chem. Rev. 105 2005 2999 3093
49. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G. 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, 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, and J.A. Pople Gaussian 03, Revision C.02 2004 Gaussian Wallingford, CT