Premium
Phenylene‐Bridged Expanded Porphyrazines
Author(s) -
Iizuka Fumiya,
Kage Yuto,
Kobayashi Nagao,
Furuta Hiroyuki,
Shimizu Soji
Publication year - 2017
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201600482
Subject(s) - antiaromaticity , phenylene , hückel method , aromaticity , chemistry , type (biology) , condensation , polymer chemistry , crystallography , stereochemistry , organic chemistry , molecule , physics , molecular orbital , polymer , ecology , thermodynamics , biology
Novel expanded porphyrazines comprising o ‐ and p ‐phenylene units were synthesized from self‐condensation reactions of acyclic [2+1]‐type precursors prepared from 1,3‐diiminoisoindoline and the corresponding phenylenediamines. Möbius and Hückel topological structures of [4+2]‐type and [3+2]‐type expanded porphyrazines, respectively, were elucidated by X‐ray crystallography. Despite the Möbius and Hückel [4 n ]π‐electron systems, these expanded porphyrazines are virtually nonaromatic as a result of their flexible structures in solution, which may diminish intrinsic aromaticity and antiaromaticity.