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Control of Aromaticity and cis ‐/ trans ‐Isomeric Structure of Non‐Planar Hexaphyrin(2.1.2.1.2.1) and Metal Complexes
Author(s) -
Xue Songlin,
Kuzuhara Daiki,
Aratani Naoki,
Yamada Hiroko
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201906946
Subject(s) - aromaticity , chemistry , porphyrin , metal , zinc , molecule , photochemistry , organic chemistry
Vinylene‐bridged hexaphyrin(2.1.2.1.2.1) was synthesized from dipyrrolyl diphenylethenes by acid‐catalyzed condensation reactions. Freebase hexaphyrin(2.1.2.1.2.1) forms a distorted structure with non‐aromatic characteristics. The aromaticity and molecular configuration of non‐planar hexaphyrin(2.1.2.1.2.1) can be controlled by insertion of metal ions. Freebase and zinc complexes show a distorted structure without macrocyclic aromaticity, whereas copper complexes show a figure‐of‐eight structure with macrocyclic aromaticity. It is the first example of aromaticity conversion of a distorted expanded porphyrin involving vinylene bridges.