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Control of Conformation and Chirality of Nonplanar π‐Conjugated Diporphyrins Using Substituents and Axial Ligands
Author(s) -
Ito Satoru,
Hiroto Satoru,
Ousaka Naoki,
Yashima Eiji,
Shinokubo Hiroshi
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.201600105
Subject(s) - chirality (physics) , steric effects , chemistry , aryl , stereochemistry , conjugated system , ligand (biochemistry) , axial chirality , pyrazine , twist , crystallography , enantioselective synthesis , polymer , receptor , catalysis , organic chemistry , biochemistry , physics , chiral symmetry breaking , alkyl , geometry , quantum mechanics , mathematics , nambu–jona lasinio model , quark
Nonplanar conformations of pyrazine‐fused Zn II diporphyrins could be controlled by the choice of the meso ‐aryl substituents and an axial ligand on the central metals. Zn II diporphyrins bearing sterically demanding meso ‐aryl groups with ortho ‐substituents led to a twisted chiral D 2 conformation, while an achiral C 2 h form was preferred in the case of aryl groups without ortho ‐substituents. Helical chirality induction on Zn II diporphyrins in the twisted conformation was achieved by controlling their handedness of the molecular twist through coordination of optically active 1‐phenethylamine.