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Synthesis of a Highly Fluorescent Bis(1,4‐oxaborine)pentacene
Author(s) -
Lee Johnathan J. C.,
Chi Chunyan,
Wu Jishan
Publication year - 2021
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202100098
Subject(s) - pentacene , quantum yield , fluorescence , photoluminescence , chemistry , ring (chemistry) , yield (engineering) , solid state , crystallography , nucleophile , photochemistry , materials science , optoelectronics , organic chemistry , catalysis , physics , electrode , quantum mechanics , metallurgy , thin film transistor
1,4‐Oxaborines represent an expansion of the current array of heteroborines. Herein, we report a new ladder‐type bis(1,4‐oxaborine)pentacene ( BO‐Pen ), the backbone of which can be regarded as an isoelectronic structure of pentacene. The synthesis begins with a two‐fold nucleophilic aromatic substitution followed by a ring‐closing reaction. The structure was confirmed by X‐ray crystallographic analysis. Compound BO‐Pen is stable (even after 160 h) under ambient condition and exhibits very different electronic properties as compared to its all‐carbon pentacene analogue ( Pen‐M ). Particularly, it shows bright photoluminescence (73 % relative quantum yield) in both solution and in solid state.