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Modulated Photochemical Reactivities of O-Acetylated (3’,5’-Dimethoxyphenyl)heteroaryl Acyloin Derivatives Under Direct Irradiation And Photo-induced Electron Transfer Conditions

Abstract

3′,5′-dimethoxybenzoin esters are imporatnt photoremovable protecting groups which forms 2-phenylbenzofuran derivative upon photo-release. We utilized a similar concept to test a photochemical method of installing benzofuran moiety to the conjugated backbone by subjecting O-acetylated (3’,5’-dimethylphenyl)heteroaryl acyloin derivatives through direct photo irradiation and photo-induced electron transfer reaction. These photochemical methods were explored for a variety of heteroaromatic substrates appended on the ketone part of the O-acetylatedcross-acyloin derivatives. The furan, thiophene and bithiophene derivatives led to the expected cyclized (benzofuran capped) products but the derivatives with extended conjugation decomposed under direct irradiation. However, under irradiation in presence of the electron donor such as triethylamine, the extended acyloin derivatives afforded both cyclized and deacetoxylated products. Semiconducting nature of the extended cyclized products was also explored and tested for solution-processed organic field effect transistor which provided maximum hole mobility of 1.3×10-6 cm2V-1s-1.

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Publication details

The article was received on 22 Feb 2018, accepted on 15 May 2018 and first published on 15 May 2018


Article type: Paper
DOI: 10.1039/C8PP00082D
Citation: Photochem. Photobiol. Sci., 2018, Accepted Manuscript
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    Modulated Photochemical Reactivities of O-Acetylated (3’,5’-Dimethoxyphenyl)heteroaryl Acyloin Derivatives Under Direct Irradiation And Photo-induced Electron Transfer Conditions

    R. H. Bisht, S. Singh, K. Krishnamoorthy and J. Nithyanandhan, Photochem. Photobiol. Sci., 2018, Accepted Manuscript , DOI: 10.1039/C8PP00082D

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