4,7‐Bis[3‐(dimesitylboryl)thien‐2‐yl]benzothiadiazole: Solvato‐, Thermo‐, and Mechanochromism Based on the Reversible Formation of an Intramolecular B−N Bond
- 9 January 2017
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 23 (15), 3784-3791
- https://doi.org/10.1002/chem.201606041
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.Keywords
This publication has 87 references indexed in Scilit:
- Recent advances in organic mechanofluorochromic materialsChemical Society Reviews, 2012
- Aryl(hydro)boranes: versatile building blocks for boron-doped π-electron materialsDalton Transactions, 2012
- Boron based anion receptors as sensorsChemical Society Reviews, 2010
- A New Design Strategy for Organic Optoelectronic Materials by Lateral Boryl SubstitutionAngewandte Chemie-International Edition, 2008
- Design organischer optoelektronischer Materialien durch laterale BorylsubstitutionAngewandte Chemie, 2008
- Intramolecular B–N Coordination as a Scaffold for Electron‐Transporting Materials: Synthesis and Properties of Boryl‐Substituted ThienylthiazolesAngewandte Chemie, 2006
- Reproducible on–off switching of solid-state luminescence by controlling molecular packing through heat-mode interconversionNature Materials, 2005
- Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsiloleChemical Communications, 2001
- Characterization of Tricoordinate Boron Chemical Shift Tensors: Definitive High-Field Solid-State NMR Evidence for Anisotropic Boron ShieldingThe Journal of Physical Chemistry A, 2001
- Metallacarboranes in catalysis. 3. Synthesis and reactivity of exo-nido-phosphinerhodacarboranesJournal of the American Chemical Society, 1984