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Cooperative effects of o- and m-methyl groups on the intramolecular charge-transfer emission properties of dibenzoylmethanatoboron difluorides

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Abstract

The photophysical properties of o-tolyl-, m-tolyl-, and p-xylyl-substituted asymmetric diaroylmethanatoboron difluorides in a mixture of CH2Cl2 and c-C6H12, and in the crystalline state were determined. In solution, the fluorescence (FL) properties of these substances are controlled by the position and number of methyl groups on the phenyl rings. An especially interesting finding is that FL from the p-xylyl derivative occurs from an excited state which possesses intramolecular charge-transfer character caused by the o- and m-methyl groups cooperatively. The results of X-ray crystallographic analysis reveal that these asymmetric diaroylmethanatoboron difluorides form dyads through orbital overlap of neighboring molecules. This phenomenon governs the unique FL properties of these substances in the solid state.

Graphical abstract: Cooperative effects of o- and m-methyl groups on the intramolecular charge-transfer emission properties of dibenzoylmethanatoboron difluorides

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Publication details

The article was received on 07 Jan 2017, accepted on 30 Mar 2017 and first published on 31 Mar 2017


Article type: Paper
DOI: 10.1039/C7PP00005G
Citation: Photochem. Photobiol. Sci., 2017, Advance Article
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    Cooperative effects of o- and m-methyl groups on the intramolecular charge-transfer emission properties of dibenzoylmethanatoboron difluorides

    M. Tanaka, S. Muraoka, Y. Matsui, E. Ohta, T. Ogaki, K. Mizuno and H. Ikeda, Photochem. Photobiol. Sci., 2017, Advance Article , DOI: 10.1039/C7PP00005G

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