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Photoactive boron-nitrogen-carbon hybrids: from azo-borazines to polymeric materials

Oubaha, Hamid, Demitri, Nicola, Rault-Berthelot, Joëlle, Dubois, Philippe, Coulembier, Olivier and Bonifazi, Davide ORCID: 2019. Photoactive boron-nitrogen-carbon hybrids: from azo-borazines to polymeric materials. Journal of Organic Chemistry 84 (14) , pp. 9101-9116. 10.1021/acs.joc.9b01046

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In this paper, we describe synthetic routes for preparing a novel switchable BNC-based chromophore, composed of a borazine core peripherally functionalized with azobenzene moieties. Capitalizing on the Pd-catalyzed Suzuki cross-coupling reaction between a tris-triflate borazine and an organoboron azobenzene derivative, a photoswtichable azo-borazine derivative was successfully prepared. The molecule showed reversible E/Z photoisomerization upon irradiation at the maximum of the intense π–π* absorption feature (360 nm). X-ray crystallographic investigations revealed a nonplanar orientation of the three azobenzene moieties and the trans configuration of the −N═N– bonds. Building on the synthetic versatility of the borazine-azobenzene derivative, we used this photoactive scaffold to engineer soluble BN-doped polythiophene polymers. Photophysical characterization performed in solvents of different polarity suggested that the polymer undergoes intramolecular charge transfer (ICT).

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 0022-3263
Date of First Compliant Deposit: 1 July 2019
Date of Acceptance: 19 June 2019
Last Modified: 27 Oct 2022 03:45

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