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Phthalocyanine-Cored Fluorophores with Fluorene-Containing Peripheral Two-Photon Antennae as Photosensitizers for Singlet Oxygen Generation.
Abid, Seifallah; Hassine, Sarra Ben; Richy, Nicolas; Camerel, Franck; Jamoussi, Bassem; Blanchard-Desce, Mireille; Mongin, Olivier; Paul, Frédéric; Paul-Roth, Christine O.
Afiliación
  • Abid S; Univ Rennes, INSA Rennes, CNRS, UMR 6226 (Institut des Sciences Chimiques de Rennes), F-35000 Rennes, France.
  • Hassine SB; Faculté des Sciences de Bizerte, Université de Carthage, 7021 Jarzouna, Tunisie.
  • Richy N; Univ Rennes, INSA Rennes, CNRS, UMR 6226 (Institut des Sciences Chimiques de Rennes), F-35000 Rennes, France.
  • Camerel F; Campus Universitaire Farhat Hached, Université de Tunis El Manar, B.P. n° 94-ROMMANA, Tunis 1068, Tunisie.
  • Jamoussi B; Univ Rennes, INSA Rennes, CNRS, UMR 6226 (Institut des Sciences Chimiques de Rennes), F-35000 Rennes, France.
  • Blanchard-Desce M; Univ Rennes, INSA Rennes, CNRS, UMR 6226 (Institut des Sciences Chimiques de Rennes), F-35000 Rennes, France.
  • Mongin O; Department of Environmental Sciences, Faculty of Meteorology, Environment and Arid Land Agriculture, King Abdulaziz University, Jeddah 2798-22253, Saudi Arabia.
  • Paul F; Institut des Sciences Moléculaires (CNRS UMR 5255), Univ. Bordeaux, 33405 Talence, France.
  • Paul-Roth CO; Univ Rennes, INSA Rennes, CNRS, UMR 6226 (Institut des Sciences Chimiques de Rennes), F-35000 Rennes, France.
Molecules ; 25(2)2020 Jan 07.
Article en En | MEDLINE | ID: mdl-31936003
: A series of free base and Zn(II) phthalocyanines featuring fluorenyl antennae linked by methoxy or oxo bridges to the phthalocyanine core (Pc) were synthesized and characterized. Selected linear and nonlinear (two-photon absorption) optical properties of these new compounds were subsequently studied. As previously observed for related porphyrin dendrimers bearing 2-fluorenyl peripheral dendrons, an efficient energy transfer occurs from the peripheral antennae to the central phthalocyanine core following excitation in the fluorenyl-based π-π* absorption band of these chromophores. Once excited, these compounds relax to the ground state, mostly by emitting intense red light or by undergoing intersystem crossing. As a result, the tetrafunctionalized Zn(II) phthalocyanines are fluorescent, but can also efficiently photosensitize molecular oxygen in tetrahydrofurane (THF), forming singlet oxygen with nearly comparable yields to bare Zn(II) phthalocyanine (ZnPc). In comparison with the latter complex, the positive role of the fluorenyl-containing antennae on one- and two-photon brightness (2PA) is presently demonstrated when appended in peripheral (ß) position to the phthalocyanine core. Furthermore, when compared to known porphyrin analogues, the interest in replacing the porphyrin by a phthalocyanine as the central core to obtain more fluorescent two-photon oxygen photosensitizers is clearly established. As such, this contribution paves the way for the future development of innovative biphotonic photosensitizers usable in theranostics.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Fármacos Fotosensibilizantes / Oxígeno Singlete / Fluorenos / Indoles Idioma: En Revista: Molecules Asunto de la revista: BIOLOGIA Año: 2020 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Suiza
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Fármacos Fotosensibilizantes / Oxígeno Singlete / Fluorenos / Indoles Idioma: En Revista: Molecules Asunto de la revista: BIOLOGIA Año: 2020 Tipo del documento: Article País de afiliación: Francia Pais de publicación: Suiza