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Issue 22, 2017
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Design, synthesis and photophysical studies of styryl-based push–pull fluorophores with remarkable solvatofluorochromism

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Abstract

A library of 20 styryl-based push–pull dyes derived from 6-amino substituted benzothiazoles were prepared by an efficient and practical synthetic route from low-cost starting materials. The dyes were firstly designed to present an effective anchoring site for subsequent conjugation. A series of aryl scaffolds, from substituted phenyl rings containing electron donating and withdrawing groups to polycyclic aromatic derivatives, were screened. The inductive effect of N-alkyl substituted benzothiazoles was also explored for three different arrangements. The investigation of the structure–photophysics relationship was performed by UV-vis absorption and steady-state fluorescence emission measurements in solution and by TD-DFT calculations. The dyes presented high brightness, absorption bands in the visible range (∼370–453 nm) and large solvatofluorochromism comprising all the visible spectrum, as a consequence of the strong intramolecular charge transfer (ICT) nature of their excited state.

Graphical abstract: Design, synthesis and photophysical studies of styryl-based push–pull fluorophores with remarkable solvatofluorochromism

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Publication details

The article was received on 22 Aug 2017, accepted on 13 Oct 2017 and first published on 16 Oct 2017


Article type: Paper
DOI: 10.1039/C7NJ03142D
Citation: New J. Chem., 2017,41, 13760-13772
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    Design, synthesis and photophysical studies of styryl-based push–pull fluorophores with remarkable solvatofluorochromism

    M. Safir Filho, S. Fiorucci, A. R. Martin and R. Benhida, New J. Chem., 2017, 41, 13760
    DOI: 10.1039/C7NJ03142D

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