New fluorescent tetraphenylporphyrin-based dendrimers with alkene-linked fluorenyl antennae designed for oxygen sensitization
The design of porphyrin-based dendrimers featuring conjugated fluorenyl dendrons via alkene spacers allows evaluating the importance of the role of these spacers on the optical properties of interest. In the continuation of previous studies, a second-generation porphyrin-based dendrimer was synthesi...
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| Format: | Article |
| Language: | English |
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Académie des sciences
2021-07-01
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| Series: | Comptes Rendus. Chimie |
| Subjects: | |
| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.99/ |
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| author | Yao, Dandan Shi, Limiao Sun, Zhipeng Blanchard-Desce, Mireille Mongin, Olivier Paul, Frédéric Paul-Roth, Christine O. |
| author_facet | Yao, Dandan Shi, Limiao Sun, Zhipeng Blanchard-Desce, Mireille Mongin, Olivier Paul, Frédéric Paul-Roth, Christine O. |
| author_sort | Yao, Dandan |
| collection | DOAJ |
| description | The design of porphyrin-based dendrimers featuring conjugated fluorenyl dendrons via alkene spacers allows evaluating the importance of the role of these spacers on the optical properties of interest. In the continuation of previous studies, a second-generation porphyrin-based dendrimer was synthesized and metalated by Zn(II) along with its known first-generation homologue. The targeted free-base porphyrin was obtained by repetitively cycling a Michaelis–Arbuzov reaction and a Horner–Wadsworth–Emmons reaction to construct the desired vinyl-containing dendrons. After metalation by Zn(II), meso-tetraphenylporphyrin-cored dendrimers with eight (ZnTPP-D1) and sixteen (ZnTPP-D2) fluorenyl arms at their periphery were eventually isolated. These species allow evaluating the influence of the central metal and of the 1,2-alkyne for 1,2-alkene exchange on fluorescence, oxygen photosensitization, and two-photon absorption. Such structure–property relationships are currently needed for the design of optimal dendrimeric photosensitizers allowing combined two-photon-based photodynamic therapy (2P-PDT) and imaging. |
| first_indexed | 2024-03-11T16:14:26Z |
| format | Article |
| id | doaj.art-a6a43164f5064876a6d175fa09c448e3 |
| institution | Directory Open Access Journal |
| issn | 1878-1543 |
| language | English |
| last_indexed | 2024-03-11T16:14:26Z |
| publishDate | 2021-07-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj.art-a6a43164f5064876a6d175fa09c448e32023-10-24T14:23:03ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432021-07-0124S3577010.5802/crchim.9910.5802/crchim.99New fluorescent tetraphenylporphyrin-based dendrimers with alkene-linked fluorenyl antennae designed for oxygen sensitizationYao, Dandan0Shi, Limiao1Sun, Zhipeng2Blanchard-Desce, Mireille3https://orcid.org/0000-0002-1572-9545Mongin, Olivier4https://orcid.org/0000-0002-7743-9623Paul, Frédéric5https://orcid.org/0000-0002-8256-0129Paul-Roth, Christine O.6https://orcid.org/0000-0001-8367-7655Univ Rennes, INSA Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) – UMR 6226, F-35000 Rennes, FranceUniv Rennes, INSA Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) – UMR 6226, F-35000 Rennes, FranceUniv Rennes, INSA Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) – UMR 6226, F-35000 Rennes, FranceUniversité de Bordeaux, Institut des Sciences Moléculaires (CNRS UMR 5255), 33405 Talence, FranceUniv Rennes, INSA Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) – UMR 6226, F-35000 Rennes, FranceUniv Rennes, INSA Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) – UMR 6226, F-35000 Rennes, FranceUniv Rennes, INSA Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) – UMR 6226, F-35000 Rennes, FranceThe design of porphyrin-based dendrimers featuring conjugated fluorenyl dendrons via alkene spacers allows evaluating the importance of the role of these spacers on the optical properties of interest. In the continuation of previous studies, a second-generation porphyrin-based dendrimer was synthesized and metalated by Zn(II) along with its known first-generation homologue. The targeted free-base porphyrin was obtained by repetitively cycling a Michaelis–Arbuzov reaction and a Horner–Wadsworth–Emmons reaction to construct the desired vinyl-containing dendrons. After metalation by Zn(II), meso-tetraphenylporphyrin-cored dendrimers with eight (ZnTPP-D1) and sixteen (ZnTPP-D2) fluorenyl arms at their periphery were eventually isolated. These species allow evaluating the influence of the central metal and of the 1,2-alkyne for 1,2-alkene exchange on fluorescence, oxygen photosensitization, and two-photon absorption. Such structure–property relationships are currently needed for the design of optimal dendrimeric photosensitizers allowing combined two-photon-based photodynamic therapy (2P-PDT) and imaging.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.99/PorphyrinFluorenylFluorescenceEnergy transferDouble bondDendrimerPhotodynamic therapy |
| spellingShingle | Yao, Dandan Shi, Limiao Sun, Zhipeng Blanchard-Desce, Mireille Mongin, Olivier Paul, Frédéric Paul-Roth, Christine O. New fluorescent tetraphenylporphyrin-based dendrimers with alkene-linked fluorenyl antennae designed for oxygen sensitization Comptes Rendus. Chimie Porphyrin Fluorenyl Fluorescence Energy transfer Double bond Dendrimer Photodynamic therapy |
| title | New fluorescent tetraphenylporphyrin-based dendrimers with alkene-linked fluorenyl antennae designed for oxygen sensitization |
| title_full | New fluorescent tetraphenylporphyrin-based dendrimers with alkene-linked fluorenyl antennae designed for oxygen sensitization |
| title_fullStr | New fluorescent tetraphenylporphyrin-based dendrimers with alkene-linked fluorenyl antennae designed for oxygen sensitization |
| title_full_unstemmed | New fluorescent tetraphenylporphyrin-based dendrimers with alkene-linked fluorenyl antennae designed for oxygen sensitization |
| title_short | New fluorescent tetraphenylporphyrin-based dendrimers with alkene-linked fluorenyl antennae designed for oxygen sensitization |
| title_sort | new fluorescent tetraphenylporphyrin based dendrimers with alkene linked fluorenyl antennae designed for oxygen sensitization |
| topic | Porphyrin Fluorenyl Fluorescence Energy transfer Double bond Dendrimer Photodynamic therapy |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.99/ |
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