Journal
NEW JOURNAL OF CHEMISTRY
Volume 41, Issue 22, Pages 13760-13772Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7nj03142d
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Funding
- CNRS
- University of Nice Sophia Antipolis
- CAPES [99999.0011495/2015-01]
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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 (similar to 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.
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