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Elucidation of π‐Conjugation Modes in Diarene‐Fused 1,2‐Dihydro‐1,2‐diborin Dianions
Author(s) -
Araki Takafumi,
Wakamiya Atsushi,
Mori Kenji,
Yamaguchi Shigehiro
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200055
Subject(s) - tricyclic , chemistry , skeleton (computer programming) , stereochemistry , absorption (acoustics) , molecule , ring (chemistry) , absorption spectroscopy , crystallography , organic chemistry , materials science , physics , quantum mechanics , computer science , composite material , programming language
A series of diarene‐fused 1,2‐dihydro‐1,2‐diborins were prepared as a new BB‐bond‐embedded polycyclic π‐electron system. The reduction of these compounds with metals produced their corresponding dianions, the π‐conjugation modes of which varied from 6π‐conjugation within the central 1,2‐diborin skeleton to 14π peripheral conjugation over the tricyclic skeleton, depending on the nature of the reduced biaryl framework. Moreover, the countercation to the dianions had a significant effect on the absorption spectra, with a dramatic color change from yellow to deep blue, depending on the distance between the tricyclic dianion skeleton and the countercation.