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SnCl2-catalyzed synthesis of dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline and dihydroindeno[2,1-b]pyrazolo[4,3-e]pyridine with high fluorescence and their photophysical properties

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Abstract

A series of high-performance chromophores, namely pyrazoloquinoline- and pyrazolopyridine-based derivatives bearing donor–acceptor (D–A) substituent groups on the phenyl ring, was synthesized by a mild reaction. Photophysical studies, including spectral analysis and single crystal X-ray diffraction, were conducted in order to investigate how the substituent affects the solution and examine the solid-state optical properties of the derivatives. Pyrazoloquinoline derivatives exhibited redshifted absorption, emission maxima wavelengths, and higher Stokes shift values than the corresponding pyrazolopyridine derivatives in chloroform. The dimethylamino-substituted derivatives displayed aggregation induced emission (AIE) and also positive solvatochromism in the fluorescence spectrum, which was due to a more polarized, excited state than the ground state. Noticeable acidochromism was observed for the dimethylamino-substituted group in acetonitrile solvent due to the addition of trifluoroacetic acid, which induced protonation at the pyridine segment and enhanced blueshifted emission.

Graphical abstract: SnCl2-catalyzed synthesis of dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline and dihydroindeno[2,1-b]pyrazolo[4,3-e]pyridine with high fluorescence and their photophysical properties

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Publication details

The article was received on 23 Sep 2017, accepted on 28 Nov 2017 and first published on 29 Nov 2017


Article type: Paper
DOI: 10.1039/C7NJ03654J
Citation: New J. Chem., 2018, Advance Article
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    SnCl2-catalyzed synthesis of dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline and dihydroindeno[2,1-b]pyrazolo[4,3-e]pyridine with high fluorescence and their photophysical properties

    S. Manickam, U. Balijapalli and K. I. Sathiyanarayanan, New J. Chem., 2018, Advance Article , DOI: 10.1039/C7NJ03654J

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