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Issue 11, 2017
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Design of bond-cleavage-induced intramolecular charge transfer emission with dibenzoboroles and their application to ratiometric sensors for discriminating chain lengths of alkanes

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Abstract

Dibenzoborole derivatives containing four-coordinated boron were designed to realize emission from the bond-cleavage-induced intramolecular charge transfer (BICT) transition. A series of electron-donating and accepting groups were introduced into dibenzoborole through regioselective bromination and Suzuki–Miyaura coupling reaction in high yields. The synthesized dibenzoboroles showed dual-emissive properties composed of emission from the π–π* transition with four-coordinated boron and the BICT transition with a three-coordinated state. The influence of the substituents on the optical properties was experimentally and theoretically analyzed. Next, on the basis of the dual-emissive properties, it was demonstrated that dibenzoborole was feasible as a ratiometric fluorescent sensor for discriminating the viscosity of solvent alkanes including the length of alkane chains with a wide detection range. Finally, it was demonstrated that this detection system with a ratiometric output was applicable for evaluating viscosity with mixture samples and various kinds of natural oils.

Graphical abstract: Design of bond-cleavage-induced intramolecular charge transfer emission with dibenzoboroles and their application to ratiometric sensors for discriminating chain lengths of alkanes

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Publication details

The article was received on 02 Aug 2017, accepted on 03 Sep 2017 and first published on 11 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QM00350A
Citation: Mater. Chem. Front., 2017,1, 2368-2375
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    Design of bond-cleavage-induced intramolecular charge transfer emission with dibenzoboroles and their application to ratiometric sensors for discriminating chain lengths of alkanes

    T. Matsumoto, H. Takamine, K. Tanaka and Y. Chujo, Mater. Chem. Front., 2017, 1, 2368
    DOI: 10.1039/C7QM00350A

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