Conformational and configurational analysis of 4,4'-biphenanthryl derivatives and related helicenes by circular dichroism spectroscopy and cholesteric induction in nematic mesophases

被引:64
作者
Gottarelli, G
Proni, G
Spada, GP
Fabbri, D
Gladiali, S
Rosini, C
机构
[1] UNIV BOLOGNA,DIPARTIMENTO CHIM ORGAN A MANGINI,I-40127 BOLOGNA,ITALY
[2] UNIV SASSARI,DIPARTIMENTO CHIM,I-07100 SASSARI,ITALY
[3] UNIV PISA,DIPARTIMENTO CHIM & CHIM IND,I-56126 PISA,ITALY
[4] UNIV BASILICATA,DIPARTIMENTO CHIM,I-80500 POTENZA,ITALY
关键词
D O I
10.1021/jo951823n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Coupling the analysis of circular dichroism (CD) spectra with the study of cholesteric mesophases induced in nematic liquid crystals (LC) allows one to deduce some stereochemical features of 3,3'disubstituted-4,4'-biphenanthryl derivatives. The exciton coupling model can explain the CD spectra of the open-chain derivatives, thus confirming their absolute configuration; the LC technique indicates an s-trans conformation in agreement with molecular mechanics computations. Compounds with a bridge between the 3 and 3' positions are conformationally rigid and similar in shape, and their absolute configuration can be predicted by the LC technique. On the other hand, their CD spectra are different and not easy to interpret as a consequence of the different chromophores present.
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页码:2013 / 2019
页数:7
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