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Issue 2, 2014
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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.

Graphical abstract: Anthracene photodimerization in a bis-chromophoric hydrogen-bonding receptor

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Publication details

The article was received on 12 Sep 2013, accepted on 27 Oct 2013 and first published on 26 Nov 2013


Article type: Paper
DOI: 10.1039/C3PP50322D
Photochem. Photobiol. Sci., 2014,13, 316-323

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    Anthracene photodimerization in a bis-chromophoric hydrogen-bonding receptor

    C. Liang, J. Desvergne and D. M. Bassani, Photochem. Photobiol. Sci., 2014, 13, 316
    DOI: 10.1039/C3PP50322D

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