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4,7‐Bis[3‐(dimesitylboryl)thien‐2‐yl]benzothiadiazole: Solvato‐, Thermo‐, and Mechanochromism Based on the Reversible Formation of an Intramolecular B−N Bond
Author(s) -
Shimogawa Hiroyuki,
Yoshikawa Osamu,
Aramaki Yoshitaka,
Murata Michihisa,
Wakamiya Atsushi,
Murata Yasujiro
Publication year - 2017
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.201606041
Subject(s) - intramolecular force , steric effects , chemistry , molecule , crystallography , boron , derivative (finance) , computational chemistry , photochemistry , stereochemistry , organic chemistry , financial economics , economics
Abstract 4,7‐Bis‐[3‐(dimesitylboryl)thien‐2‐yl]benzothiadiazole ( 1 ) and monoborylated derivative 2 were synthesized and their chromic behavior was investigated. Photophysical measurements, single‐crystal XRD analysis, and theoretical calculations revealed that an intramolecular B−N coordination bond formed reversibly. The equilibrium of this reversible bond formation depends on the solid‐state structure, solvent, temperature, and mechanical forces, and leads to significant changes in the electronic structure and chromic behavior of these molecules. The responsiveness toward external stimuli, resulting in the reversible formation of open and closed forms of this system, is achieved through weak intramolecular B−N coordination bonds induced by the steric bulk of the mesityl groups on the boron centers.