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Systematic Synthesis of Diphenyl‐Substituted Carotenoids as Molecular Wires
Author(s) -
Lim Boram,
Oh EunTaek,
Im JongOne,
Lee Kyu Sang,
Jung Hyunuk,
Kim Minsoo,
Kim Dahye,
Oh Jung Taek,
Bae SungHee,
Chung WookJin,
Ahn KwangHyun,
Koo Sangho
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701229
Subject(s) - substituent , chemistry , carotenoid , stereoselectivity , sulfone , stereochemistry , organic chemistry , catalysis , biochemistry
A general method for the construction of diphenyl‐substituted carotenoids has been developed through the stereoselective synthesis of dienyl sulfones with a phenyl substituent. Systematic synthetic pathways to the dienyl sulfones were delineated starting from readily available acetophenones with para ‐substituent X of various electronic natures, which provided the carotenoids with diverse physicochemical characteristics. The sulfone olefination method together with the Ramberg–Bäcklund reaction produced a 9,9′‐ cis ‐10,10′‐diphenylcarotene and all‐ trans ‐9,9′‐diphenylcarotenes. Conductance measurements of the all‐ trans carotenoids by the scanning tunnelling microscopy break‐junction method revealed a positional effect of the phenyl groups as well as a polar effect of the phenyl substituent X according to the electronic nature.