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Synthesis and photophysical properties of extended π conjugated naphthalimides

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Abstract

A series of π conjugated naphthalimide derivatives having an imide group as an acceptor conjugated with a methoxy arylethynyl or a methoxyphenyl triazole as a donor were prepared by Sonogashira coupling or “click” chemistry. Their photophysical properties were investigated by steady state and time resolved fluorescence spectroscopy and modelled by TD-DFT calculations. Compound Naphth-AlkyneOMe has a high fluorescence quantum yield and displays efficient photoinduced charge transfer in solution as well as in the powder state. Compound Naphth-TriazoleOMe exhibits a very high Stokes shift and its fluorescence quantum yield is low, which can be rationalized by theoretical calculations.

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Acknowledgments

We gratefully thank Dr Gilles Clavier for fruitful discussions and advice on DFT calculations, and Arnaud Brosseau for his help with transient absorption measurements.

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Authors and Affiliations

  1. PPSM, ENS Cachan, CNRS, Université Paris Saclay, France

    C. Rémy, C. Allain & I. Leray

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  1. C. Rémy
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  2. C. Allain
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  3. I. Leray
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Correspondence to I. Leray.

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Rémy, C., Allain, C. & Leray, I. Synthesis and photophysical properties of extended π conjugated naphthalimides. Photochem Photobiol Sci 16, 539–546 (2017). https://doi.org/10.1039/c6pp00372a

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  • DOI: https://doi.org/10.1039/c6pp00372a

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