Highly emissive dimesitylboryl-substituted 2,1,3-benzothiadiazole derivatives: photophysical properties and efficient fluorescent sensor for fluoride anions

One symmetrical and two unsymmetrical dimesitylboryl-substituted BTD derivatives 1–3 were prepared through Pd(0)-catalyzed Suzuki coupling reaction. All these compounds display intense fluorescence not only in solution but also in the solid state due to steric bulkiness of the boryl group, which is...

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Bibliographic Details
Published in:Tetrahedron 2014-09, Vol.70 (35), p.5488-5493
Main Authors: Wang, Bin, Pan, Hong, Jia, Jiong, Ge, Yan-Qing, Cai, Wen-Qing, Wang, Jian-Wu, Zhao, Cui-Hua
Format: Article
Language:English
Subjects:
2,1,3-Benzothiadiazole
Chemical reactions
Complexation
Derivatives
Dimesitylboryl group
Fluorescence
Fluorescent sensor
Fluoride ions
Fluorides
Intense fluorescence
Sensors
Solid state
Utilities
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Summary:One symmetrical and two unsymmetrical dimesitylboryl-substituted BTD derivatives 1–3 were prepared through Pd(0)-catalyzed Suzuki coupling reaction. All these compounds display intense fluorescence not only in solution but also in the solid state due to steric bulkiness of the boryl group, which is effective to suppress the intermolecular interactions in the solid state. In addition, the boryl-substituted BTD 1 displays prompt fluorescence responses to fluoride ions with high sensitivity through the complexation of the boron center with fluoride, demonstrating its potential utility as fluorescent sensor for fluoride ions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.06.110