Journal
TETRAHEDRON
Volume 71, Issue 7, Pages 1088-1094Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.12.084
Keywords
8-Br-Quinolines; Friedlander reaction; Singlet oxygen production; Two-photon absorption; Fluorescence
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Funding
- Conseil Regional d'Aquitaine (Chaire d'Accueil grant)
- Agence Nationale pour la Recherche [ANR-10-NANO-022-01, ANR-10-BLAN-1436]
- Agence Nationale de la Recherche (ANR) [ANR-10-BLAN-1436] Funding Source: Agence Nationale de la Recherche (ANR)
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The present study describes the synthesis of a series of original 8-Br-quinoline derivatives with an arylethynyl moiety at the C6 position, based on Friedlander and Sonogashira coupling key reactions. Investigation of their photophysical and two-photon absorption (2PA) properties reveals that these structures can lead to 2PA chromophores combining fluorescence and singlet oxygen generation properties. As a result, chromophores, which combine significant 2PA responses in the NIR region, good photosensitization ability (Phi(Delta)=0.4-0.6) and fluorescence properties (Phi(f)=0.2-0.6) have been identified. These multifunctional derivatives hold promise as original dyes for combined two-photon imaging and photodynamic therapy. (C) 2015 Elsevier Ltd. All rights reserved.
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