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New Types of Planar Chiral [2.2]Paracyclophanes and Construction of One‐Handed Double Helices
Author(s) -
Morisaki Yasuhiro,
Sawada Risa,
Gon Masayuki,
Chujo Yoshiki
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201601028
Subject(s) - planar , regioselectivity , sonogashira coupling , planar chirality , luminescence , photoluminescence , chirality (physics) , stereochemistry , crystallography , materials science , chemistry , enantioselective synthesis , physics , optoelectronics , organic chemistry , catalysis , palladium , chiral symmetry , computer science , quantum mechanics , computer graphics (images) , quark , nambu–jona lasinio model
New types of planar chiral ( R p )‐ and ( S p )‐4,7,12,15‐tetrasubstituted [2.2]paracyclophanes were synthesized from racemic 4,12‐dihydroxy[2.2]paracyclophane as the starting compound. Regioselective dibromination and transformation afforded a series of planar chiral ( R p )‐ and ( S p )‐4,7,12,15‐tetrasubstituted [2.2]paracyclophanes, which can be used as chiral building blocks. In this study, left‐ and right‐handed double helical structures were constructed via chemoselective Sonogashira–Hagihara coupling. The double helical compounds were excellent circularly polarized luminescence (CPL) emitters with large molar extinction coefficients, good photoluminescence quantum efficiencies, and large CPL dissymmetry factors.