Electrochiroptical systems based on biphenyl-2,2′-diyl-type dicationic dyes: strong chiroptical signals through the transmission of point chirality to axial chirality

Tetrahedron Letters

Volumn 48, Issue 20, 2007, Pages 3599-3603

  Suzuki, Takanori ^a   Iwai, Tomohiro ^a   Ohta, Eisuke ^a   Kawai, Hidetoshi ^a   Fujiwara, Kenshu ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Chirality; Chiroptical enhancement; Dynamic redox system; Electrochiroptics; Hexaphenylethane

Indexed keywords

BENZENE; BIPHENYL DERIVATIVE; CATION; DYE; SOLVENT;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; DIASTEREOISOMER; ELECTROCHEMICAL ANALYSIS; ELECTROLYSIS; OPTICAL ROTATION; OXIDATION REDUCTION REACTION; QUANTUM YIELD; ULTRAVIOLET SPECTROSCOPY;

EID: 34247141471     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.080     Document Type: Article

References (25)

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7. Metal complexes with chiral ligands were also shown to exhibit CD signal change upon redox reaction of the metal center:. Zahn S., and Canary J.W. J. Am. Chem. Soc. 124 (2002) 9204
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15. 7b). Yet, the molecule racemizes rapidly when the crystal of pure enantiomer is dissolved into a solution.
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17. Very recently we reported the chiral redox system where the point chirality is effectively transmitted to helicity:. Suzuki T., Tanaka S., Kawai H., and Fujiwara K. Chem. Asian J. 2 (2007) 171
18. Mori T., and Inoue Y. J. Phys. Chem. A 109 (2005) 2728
19. Suzuki T., Higuchi H., Tsuji T., Nishida J., Yamashita Y., and Miyashi T. In: Nakamura T., Matsumoto T., Tada H., and Sugiura K. (Eds). Chemistry of Nanomolecular Systems, Chapter 1: Dynamic Redox Systems (2003), Springer, Heidelberg 3
20. Suzuki T., Ohta E., Kawai H., Fujiwara K., and Fukushima T. Synlett (2007) 851
21. 4{A figure is presented}.
22. The value is close to that measured for the dication of tetrakis[4-(R)-sec-butoxyphenyl]ethylene (Ref. 11), in which two bis[4-(R)-sec-butoxyphenyl]methylium chromophores are directly connected.
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24. Significant solvent effects on the diastereomeric preference in terms of helicity were described previously:. Yagi S., Morinaga T., Nomura T., Takagishi T., Mizutani T., Kitagawa S., and Ogoshi H. J. Org. Chem. 66 (2001) 3848
25. -1. The final R value is 0.072 for 11,286 independent reflections, 1296 parameters. CCDC 636050.