1401545-19-4Relevant academic research and scientific papers
Photo- and thermal-induced multistructural transformation of 2-phenylazolyl chelate boron compounds
Rao, Ying-Li,Amarne, Hazem,Chen, Leanne D.,Brown, Matthew L.,Mosey, Nicholas J.,Wang, Suning
, p. 3407 - 3410 (2013/04/23)
The new N,C-chelate boron compounds B(2-phenylazolyl)Mes2 [Mes = mesityl; azolyl = benzothiazolyl (1a), 4-methylthiazolyl (2a), benzoxazolyl (3a), benzimidazolyl (4a)] undergo an unprecedented multistructural transformation upon light irradiation or heating, sequentially producing isomers b, c, d, and e. The dark isomers b generated by photoisomerization of a undergo a rare thermal intramolecular H-atom transfer (HAT), reducing the azole ring and generating new isomers c, which are further transformed into isomers d. Remarkably, isomers d can be converted to their diastereomers e quantitatively by heating, and e can be converted back to d by irradiation at 300 nm. The structures of isomers 1d and 1e were established by X-ray diffraction. The unusual HAT reactivity can be attributed to the geometry of the highly energetic isomers b and the relatively low aromaticity of the azole rings. The boryl unit plays a key role in the reversible interconversion of d and e, as shown by mechanistic pathways established through DFT and TD-DFT calculations.
Boron Compounds and Uses Thereof
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Page/Page column 11, (2012/10/08)
Organoboron compounds are described that upon exposure to light absorb light and isomerize and form a dark-colored isomer. The dark-colored isomer converts back to the colorless isomer upon removal of light, or exposure to oxygen or heat. Such compounds c
