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Photochem Photobiol Sci. 2012 Nov;11(11):1756-66. doi: 10.1039/c2pp25258a. Epub 2012 Sep 17.

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

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


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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