Nonclassical tunability of solid-state CD and CPL properties of a chiral 2-naphthalenecarboxylic acid/amine supramolecular organic fluorophore

Chemistry - An Asian Journal

Volumn 7, Issue 2, 2012, Pages 360-366

  Nishiguchi, Noriaki ^a   Kinuta, Takafumi ^a   Sato, Tomohiro ^a   Nakano, Yoko ^b   Tokutome, Hayato ^c   Tajima, Nobuo ^d   Fujiki, Michiya ^b   Kuroda, Reiko ^c   Matsubara, Yoshio ^a   Imai, Yoshitane ^a  

^a KINKI UNIVERSITY   (Japan)

^b NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

^d NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

chirality; crystal engineering; fluorescence; luminescence; supramolecular chemistry

Indexed keywords

ARYL UNITS; CIRCULARLY POLARIZED LUMINESCENCE; ORGANIC FLUOROPHORES; TUNABILITIES;

CHIRALITY; CRYSTAL ENGINEERING; DICHROISM; ENANTIOMERS; FLUORESCENCE; FLUOROPHORES; LUMINESCENCE; SUPRAMOLECULAR CHEMISTRY;

STEREOCHEMISTRY;

EID: 84863011897     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201100727     Document Type: Article

References (31)

1. J. Shinar, Organic Light-Emitting Devices, Springer, Heidelberg, 2004
2. K. Müllen, U. Scherf, Organic Light-Emitting Devices, Wiley-VCH, Weinheim, 2006
3. C. Jeanne, R. Regis, Dalton Trans. 2008, 6865-6876
4. S. Kappaun, C. Slugovc, J. M. Emil, Int. J. Mol. Sci. 2008, 9, 1527-1547
5. K. Milan, O. Franc, Acc. Chem. Res. 2009, 42, 235-248
6. W.-Y. Wong, C.-L. Ho, J. Mater. Chem. 2009, 19, 4457-4482
7. K.-L. Chan, P. Sonar, A. Sellinge, J. Mater. Chem. 2009, 19, 9103-9120
8. F. Laquai, Y.-S. Park, J.-J. Kim, T. Basche, Macromol. Rapid Commun. 2009, 30, 1203-1231
9. C. Wang, J. Zhang, K. Ryu, A. Badmaev, L. G. D. Arco, C. Zhou, Nano Lett. 2009, 9, 4285-4291
10. M.-K. Wei, C.-W. Lin, C.-C. Yang, Y.-W. Kiang, J.-H. Lee, H.-Y. Lin, Int. J. Mol. Sci. 2010, 11, 1527-1545, and references cited therein.
11. Y. Mizobe, N. Tohnai, M. Miyata, Y. Hasegawa, Chem. Commun. 2005, 1839-1841
12. S. Oshita, A. Matsumoto, Langmuir 2006, 22, 1943-1945
13. Y. Mizobe, M. Miyata, I. Hisaki, Y. Hasegawa, N. Tohnai, Org. Lett. 2006, 8, 4295-4298
14. Y. Imai, K. Kawaguchi, T. Harada, T. Sato, M. Ishikawa, M. Fujiki, R. Kuroda, Y. Matsubara, Tetrahedron Lett. 2007, 48, 2927-2930
15. Y. Imai, K. Murata, K. Kawaguchi, T. Sato, R. Kuroda, Y. Matsubara, Org. Lett. 2007, 9, 3457-3460
16. Y. Mizobe, T. Hinoue, M. Miyata, I. Hisaki, Y. Hasegawa, N. Tohnai, Bull. Chem. Soc. Jpn. 2007, 80, 1162-1172
17. Y. Imai, K. Murata, K. Kawaguchi, T. Sato, N. Tajima, R. Kuroda, Y. Matsubara, Chem. Asian J. 2008, 3, 625-629
18. Y. Imai, K. Nagasaki, K. Murata, K. Kawaguchi, T. Harada, Y. Nakano, T. Sato, M. Fujiki, R. Kuroda, Y. Matsubara, CrystEngComm 2008, 10, 951-953
19. Y. Imai, K. Kamon, K. Murata, T. Harada, Y. Nakano, T. Sato, M. Fujiki, R. Kuroda, Y. Matsubara, Org. Biomol. Chem. 2008, 6, 3471-3475
20. Y. Ooyama, K. Yoshida, Eur. J. Org. Chem. 2008, 2564-2570
21. J. Luo, T. Lei, L. Wang, Y. Ma, Y. Cao, J. Wang, J. Pei, J. Am. Chem. Soc. 2009, 131, 2076-2077
22. N. Shiota, T. Kinuta, T. Sato, N. Tajima, R. Kuroda, Y. Matsubara, Y. Imai, Cryst. Growth Des. 2010, 10, 1341-1345.
23. Lemmerer and co-workers have reported the crystal structure of complex I. However, since the temperature of measurement was 173 K, we remeasured this complex at 115 K to unify the measurement temperatures for complexes I-III., A. Lemmerer, S. A. Bourne, M. A. Ferandes, CrystEngComm 2008, 10, 1605-1612.
24. J. E. Ridley, M. C. Zerner, Theor. Chim. Acta 1973, 32, 111-134
25. J. E. Ridley, M. C. Zerner, Theor. Chim. Acta 1976, 42, 223-236
26. M. C. Zerner, G. H. Lowe, R. F. Kirchner, U. T. Mueller-Westerhoff, J. Am. Chem. Soc. 1980, 102, 589-599.
27. Gaussian 03, Revision E.01, 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, 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, 2004.
28. R. Kuroda, Y. Saito, Bull. Chem. Soc. Jpn. 1976, 49, 433-436.
29. SHELXL97, G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112-122.
30. A. L. Spek, PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht (Netherlands), 2010.
31. G. M. Sheldrick, SADABS, Program for Empirical Absorption Correction of Area Detector Data, University of Göttingen, Göttingen (Germany), 1996.