Premium
Chiroptical properties and racemization behavior of highly distorted donor‐acceptor tetracyanoanthraquinodimethane with interconvertible planar chirality
Author(s) -
Saito Hideaki,
Mori Tadashi,
Origane Yumi,
Wada Takehiko,
Inoue Yoshihisa
Publication year - 2008
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20427
Subject(s) - racemization , chemistry , circular dichroism , chirality (physics) , planar chirality , anthracene , planar , axial chirality , acceptor , absolute configuration , photochemistry , dichroism , stereochemistry , crystallography , enantioselective synthesis , organic chemistry , catalysis , optics , chiral symmetry , physics , computer graphics (images) , condensed matter physics , quantum mechanics , computer science , nambu–jona lasinio model , quark
Absolute configuration of optically active 7,12‐bis(dicyanomethylene)‐7,12‐dihydrobenz[ a ]anthracene ( 1 ) with interconvertible planar chirality was determined by a comparison of experimental and theoretical circular dichroism (CD) spectra. Upon standing at ambient temperatures, 1 was found to spontaneously racemize, the rates of which were assessed through the separation profiles of chiral HPLC at 5–20°C and also from the CD spectral decay profiles at the same temperatures. Mechanism of the racemization was discussed. Chirality, 2008. © 2007 Wiley‐Liss, Inc.