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Trannulenes with “In‐Plane” Aromaticity: Candidates for Harvesting Light Energy
Author(s) -
Burley Glenn A.
Publication year - 2005
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.200500362
Subject(s) - annulene , aromaticity , ring (chemistry) , atomic orbital , plane (geometry) , conjugated system , antiaromaticity , perpendicular , chemistry , computational chemistry , chemical physics , materials science , physics , geometry , organic chemistry , quantum mechanics , molecule , mathematics , electron , polymer
Breaking with convention : In the textbook aromatic annulenes the p orbitals are oriented perpendicular to the ring plane. In trannulenes the p orbitals form a cyclic, conjugated π system within the ring plane (see scheme). This concept of “in‐plane” aromaticity was first recognized in 1979, and now representative compounds have been synthesized. The all‐ trans configuration of the annulene ring is stabilized by a fullerene framework, and the novel physicochemical properties of trannulenes open new opportunities for the design of light‐harvesting compounds.