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Fluorescence and two-photon absorption of push—pull aryl(bi)thiophenes: structure—property relationships

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Abstract

Photophysical and TPA properties of series of push—pull aryl(bi)thiophene chromophores bearing electron-donating (D) and electron-withdrawing (A) end-groups of increasing strength are presented. All compounds show an intense intramolecular charge transfer (ICT) absorption band in the visible region. Increasing the D and/or A strength as well as the length of the conjugated path induces bathochromic and hyperchromic shifts of the absorption band as reported for analogous push—pull polyenes. Yet, in contrast with corresponding push—pull polyenes, a significant increase in fluorescence is observed. In particular, chromophores built from a phenyl—bithienyl conjugated path and bearing strong D and A end-groups were found to combine very large one and two-photon brightness as well as strong emission in the red/NIR region. These molecules hold promise as biphotonic fluorescent probes for bioimaging.

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Authors and Affiliations

  1. Univ. Bordeaux, ISM, UMR 5255 CNRS, F-33400, Talence, France

    Emilie Genin, Vincent Hugues, Guillaume Clermont & Mireille Blanchard-Desce

  2. Center of Chemistry, University of Minho, Campus of Gualtar, 4710-057, Braga, Portugal

    Cyril Herbivo, M. Cidália R. Castro & M. Manuela M. Raposo

  3. Institut Jean Barriol, Laboratoire de Chimie et Physique - Analyse Multi-échelles des Milieux Complexes, Université de Lorraine, F-57048, Metz Cedex, France

    Cyril Herbivo & Alain Comel

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  1. Emilie Genin
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  2. Vincent Hugues
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  3. Guillaume Clermont
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  7. M. Manuela M. Raposo
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  8. Mireille Blanchard-Desce
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Correspondence to Mireille Blanchard-Desce.

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This article is published as part of a themed issue in honour of Jean-Pierre Desvergne on the occasion of his 65th birthday.

Electronic supplementary information (ESI) available. See DOI: 10.1039/c2pp25258a

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Genin, E., Hugues, V., Clermont, G. et al. Fluorescence and two-photon absorption of push—pull aryl(bi)thiophenes: structure—property relationships. Photochem Photobiol Sci 11, 1756–1766 (2012). https://doi.org/10.1039/c2pp25258a

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