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Synthesis and Comparative Characterization of 9‐Boraanthracene, 5‐Boranaphthacene, and 6‐Borapentacene Stabilized by the H 2 IMes Carbene
Author(s) -
Wood Thomas K.,
Piers Warren E.,
Keay Brian A.,
Parvez Masood
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001922
Subject(s) - imes , carbene , transmetalation , chemistry , acene , adduct , pnictogen , methanol , boron , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , catalysis , molecule , physics , superconductivity , quantum mechanics
A general procedure for the preparation of three N‐heterocyclic carbene stabilized, boron‐containing acenes (9‐boraanthracene, 5‐boranaphthacene, and 6‐borapentacene) is presented. The key steps involve a transmetallation reaction between BCl 3 and an appropriate stannacyclic precursor, and the dehydrochlorination of the H 2 IMes adduct of the chloroborane product. Comparative structural, photophysical, and redox properties reveal narrow HOMO–LUMO gaps relative to the all‐carbon acene analogues.