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Anthracene photodimerization in a bis-chromophoric hydrogen-bonding receptor

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Abstract

The photochemistry and photophysics of a bis-anthracenyl hydrogen-bonding receptor (7-(3, 5-bis((6-(4-(anthracen-9-yloxy) butanamido)pyridin-2-yl)carbamoyl)phenylhept-6-ynoate, 2) were investigated in a fluid solution. At room temperature, fluorescence and intersystem crossing compete with intramolecular dimerization to form head-to-head and head-to-tail photoproducts, whereas fluorescence is the principal deactivation pathway at low temperature. Time-resolved fluorescence spectroscopy evidences two excimer-like emitting states whose sensitivity to quenching by oxygen is considerably lower than that of intramolecular photodimerization (KSV = ca. 450 vs. <100 L mol−1, respectively). Based on the temperature-dependence and quenching efficiency of photodimerization, a mechanism is proposed in which the ground-state conformation of the tether controls the formation of the HH vs. HT photodimers via a non-emissive intermediate.

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Authors and Affiliations

  1. Institut des Sciences Moléculaires Univ. Bordeaux 1, CNRS UMR 5255, 351 cours de la Libération, 33400, Talence, France

    Chih-Kai Liang, Jean-Pierre Desvergne & Dario M. Bassani

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  1. Chih-Kai Liang
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  2. Jean-Pierre Desvergne
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  3. Dario M. Bassani
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Correspondence to Dario M. Bassani.

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Dedicated to the memory of Prof. N. J. Turro.

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Liang, CK., Desvergne, JP. & Bassani, D.M. Anthracene photodimerization in a bis-chromophoric hydrogen-bonding receptor. Photochem Photobiol Sci 13, 316–323 (2014). https://doi.org/10.1039/c3pp50322d

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