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Pyridine‐Fused Bis(Norcorrole) through Hantzsch‐Type Cyclization: Enhancement of Antiaromaticity by an Aromatic Bridge
Author(s) -
Li Xiaofang,
Meng Yankui,
Yi Pinggui,
Stępień Marcin,
Chmielewski Piotr J.
Publication year - 2017
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.201705715
Subject(s) - antiaromaticity , moiety , chemistry , pyridine , yield (engineering) , condensation , aryl , catalysis , aromaticity , combinatorial chemistry , organic chemistry , molecule , materials science , physics , alkyl , metallurgy , thermodynamics
A non‐catalytic condensation of Ni II β‐aminonorcorrole with aryl aldehydes is shown to produce a family of pyrromethane dimers that undergo deaminative cyclization to yield pyridine‐fused bis(norcorrole)s comprising two antiaromatic macrocycles communicating by an aromatic moiety. The new compounds were characterized by spectroscopic, structural, and electrochemical methods supported by DFT calculations, all of which revealed unexpected antiaromaticity enhancement in the fused system.