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J-Aggregation induced emission enhancement of a thienyl substituted bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine (BOPHY) dye

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Abstract

The synthesis and characterization of 2,7-diphenyl- and 2,7-dithienyl-1,3,6,8-tetramethyl bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine (BOPHY) derivatives 1 and 2 are described. The compounds were characterized by NMR (1H, 13C), X-ray single crystal diffraction analysis, UV/Vis, fluorescence spectroscopy and high-resolution mass spectrometry (HRMS). The photophysical properties were investigated in solvents of different polarities. Compound 1 exhibits slight solvent dependent spectroscopic properties, whereas compound 2 shows fluorescence quenching with an increase in the solvent polarity. Aggregation-induced emission enhancement (AIEE) is observed in compound 2, which is attributed to the formation of J-aggregates that result in narrow, red-shifted and enhanced emission. Modification of the β-substituents of BOPHY is responsible for the formation of these aggregates, which is definitively established by an X-ray diffraction study.

Graphical abstract: J-Aggregation induced emission enhancement of a thienyl substituted bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine (BOPHY) dye

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Publication details

The article was received on 03 Jan 2018, accepted on 10 Apr 2018 and first published on 11 Apr 2018


Article type: Paper
DOI: 10.1039/C8NJ00031J
Citation: New J. Chem., 2018, Advance Article
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    J-Aggregation induced emission enhancement of a thienyl substituted bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine (BOPHY) dye

    L. Jiang, H. Gao, L. Gai and Z. Shen, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ00031J

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