Stepwise Oxidative C–C Coupling and/or C–N Fusion of Zn(II) meso-Pyridin-2-ylthio-porphyrins
The synthesis and characterization of zinc(II) meso-pyridin-2-ylthio-porphyrins are presented in this manuscript. The (electro)chemical oxidation of [5-(pyridin-2-ylthio)-10,20-bis(p-tolyl)-15-phenylporphyrinato] zinc(II) or [5,15-bis(pyridin-2-ylthio)-10,20-bis(p-tolyl)porphyrinato] zinc(II...
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| Veröffentlicht in: | Inorganic chemistry 2022-05, Vol.61 (19), p.7387-7405 |
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| creator | Berthelot, Mathieu Akhssas, Fatima Dimé, Abdou K. D. Bousfiha, Asmae Echaubard, Julie Souissi, Ghada Cattey, Hélène Lucas, Dominique Fleurat-Lessard, Paul Devillers, Charles H. |
| description | The synthesis and characterization of zinc(II) meso-pyridin-2-ylthio-porphyrins are presented in this manuscript. The (electro)chemical oxidation of [5-(pyridin-2-ylthio)-10,20-bis(p-tolyl)-15-phenylporphyrinato] zinc(II) or [5,15-bis(pyridin-2-ylthio)-10,20-bis(p-tolyl)porphyrinato] zinc(II) leads to the formation of one or two C–N bond(s) by intramolecular nucleophilic attack of the peripheral thiopyridinyl fragment(s) on the neighboring β-pyrrolic position(s) (C–N fusion reaction). In addition, the chemical oxidation of [5-(pyridin-2-ylthio)-10,20-bis(p-tolyl)porphyrinato] zinc(II), i.e., bearing one free meso position, mainly affords the meso,meso-dimer. Further stepwise electrochemical oxidation selectively produces the mono and bis C–N fused meso,meso-dimer. The resulting pyridinium derivatives exhibit important changes in their physicochemical properties (NMR, UV–vis, CV) as compared to their initial unfused precursors. Also, the X-ray crystallographic structures of three unfused monomers, one unfused meso,meso-dimer, and two C–N fused monomers are presented. |
| doi_str_mv | 10.1021/acs.inorgchem.2c00435 |
| format | Article |
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D. ; Bousfiha, Asmae ; Echaubard, Julie ; Souissi, Ghada ; Cattey, Hélène ; Lucas, Dominique ; Fleurat-Lessard, Paul ; Devillers, Charles H.</creator><creatorcontrib>Berthelot, Mathieu ; Akhssas, Fatima ; Dimé, Abdou K. D. ; Bousfiha, Asmae ; Echaubard, Julie ; Souissi, Ghada ; Cattey, Hélène ; Lucas, Dominique ; Fleurat-Lessard, Paul ; Devillers, Charles H.</creatorcontrib><description>The synthesis and characterization of zinc(II) meso-pyridin-2-ylthio-porphyrins are presented in this manuscript. The (electro)chemical oxidation of [5-(pyridin-2-ylthio)-10,20-bis(p-tolyl)-15-phenylporphyrinato] zinc(II) or [5,15-bis(pyridin-2-ylthio)-10,20-bis(p-tolyl)porphyrinato] zinc(II) leads to the formation of one or two C–N bond(s) by intramolecular nucleophilic attack of the peripheral thiopyridinyl fragment(s) on the neighboring β-pyrrolic position(s) (C–N fusion reaction). In addition, the chemical oxidation of [5-(pyridin-2-ylthio)-10,20-bis(p-tolyl)porphyrinato] zinc(II), i.e., bearing one free meso position, mainly affords the meso,meso-dimer. Further stepwise electrochemical oxidation selectively produces the mono and bis C–N fused meso,meso-dimer. The resulting pyridinium derivatives exhibit important changes in their physicochemical properties (NMR, UV–vis, CV) as compared to their initial unfused precursors. 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The (electro)chemical oxidation of [5-(pyridin-2-ylthio)-10,20-bis(p-tolyl)-15-phenylporphyrinato] zinc(II) or [5,15-bis(pyridin-2-ylthio)-10,20-bis(p-tolyl)porphyrinato] zinc(II) leads to the formation of one or two C–N bond(s) by intramolecular nucleophilic attack of the peripheral thiopyridinyl fragment(s) on the neighboring β-pyrrolic position(s) (C–N fusion reaction). In addition, the chemical oxidation of [5-(pyridin-2-ylthio)-10,20-bis(p-tolyl)porphyrinato] zinc(II), i.e., bearing one free meso position, mainly affords the meso,meso-dimer. Further stepwise electrochemical oxidation selectively produces the mono and bis C–N fused meso,meso-dimer. The resulting pyridinium derivatives exhibit important changes in their physicochemical properties (NMR, UV–vis, CV) as compared to their initial unfused precursors. Also, the X-ray crystallographic structures of three unfused monomers, one unfused meso,meso-dimer, and two C–N fused monomers are presented.</description><subject>Chemical Sciences</subject><subject>Crystallography, X-Ray</subject><subject>Magnetic Resonance Spectroscopy - methods</subject><subject>Oxidative Stress</subject><subject>Polymers</subject><subject>Porphyrins - chemistry</subject><subject>Zinc - chemistry</subject><issn>0020-1669</issn><issn>1520-510X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1O3DAUha2qCAbKI4CyhEWG698kSxRBGWlUkNpKVTeuJ_YwRomd2glldrwDb9gnqacznW1Xts79zrnSPQidYZhiIPhKNXFqnQ-Pzcp0U9IAMMrfoQnmBHKO4dt7NAFIfyxEdYSOY3wCgIoycYiOKOdphvEE_fg8mP6XjSa7f7FaDfbZZPXv17c6q_3Yt9Y9ZsrpKx_-qp-y2zFa7zK_zL67i9nsMutM9PnDOlhtXU7ydTusrM97H_pVEl38gA6Wqo3mdPeeoK-3N1_qu3x-_3FWX89zRQUZciZKwhYV4UUJhWGKlFhpQSuli4KVFVkC4wVjVSn4oiBKUU2ZISTNDVRaK3qCLre5K9XKPthOhbX0ysq767ncaEBLyihmzzixF1u2D_7naOIgOxsb07bKGT9GSQSvCAUqioTyLdoEH2Mwy302BrkpQqYi5L4IuSsi-c53K8ZFZ_Te9e_yCcBbYON_8mNw6Tr_Cf0DmTqX6A</recordid><startdate>20220516</startdate><enddate>20220516</enddate><creator>Berthelot, Mathieu</creator><creator>Akhssas, Fatima</creator><creator>Dimé, Abdou K. 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D.</au><au>Bousfiha, Asmae</au><au>Echaubard, Julie</au><au>Souissi, Ghada</au><au>Cattey, Hélène</au><au>Lucas, Dominique</au><au>Fleurat-Lessard, Paul</au><au>Devillers, Charles H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stepwise Oxidative C–C Coupling and/or C–N Fusion of Zn(II) meso-Pyridin-2-ylthio-porphyrins</atitle><jtitle>Inorganic chemistry</jtitle><addtitle>Inorg. Chem</addtitle><date>2022-05-16</date><risdate>2022</risdate><volume>61</volume><issue>19</issue><spage>7387</spage><epage>7405</epage><pages>7387-7405</pages><issn>0020-1669</issn><eissn>1520-510X</eissn><abstract>The synthesis and characterization of zinc(II) meso-pyridin-2-ylthio-porphyrins are presented in this manuscript. The (electro)chemical oxidation of [5-(pyridin-2-ylthio)-10,20-bis(p-tolyl)-15-phenylporphyrinato] zinc(II) or [5,15-bis(pyridin-2-ylthio)-10,20-bis(p-tolyl)porphyrinato] zinc(II) leads to the formation of one or two C–N bond(s) by intramolecular nucleophilic attack of the peripheral thiopyridinyl fragment(s) on the neighboring β-pyrrolic position(s) (C–N fusion reaction). In addition, the chemical oxidation of [5-(pyridin-2-ylthio)-10,20-bis(p-tolyl)porphyrinato] zinc(II), i.e., bearing one free meso position, mainly affords the meso,meso-dimer. Further stepwise electrochemical oxidation selectively produces the mono and bis C–N fused meso,meso-dimer. The resulting pyridinium derivatives exhibit important changes in their physicochemical properties (NMR, UV–vis, CV) as compared to their initial unfused precursors. Also, the X-ray crystallographic structures of three unfused monomers, one unfused meso,meso-dimer, and two C–N fused monomers are presented.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>35500211</pmid><doi>10.1021/acs.inorgchem.2c00435</doi><tpages>19</tpages><orcidid>https://orcid.org/0000-0003-3114-2522</orcidid><orcidid>https://orcid.org/0000-0001-9078-7035</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Chemical Sciences Crystallography, X-Ray Magnetic Resonance Spectroscopy - methods Oxidative Stress Polymers Porphyrins - chemistry Zinc - chemistry |
| title | Stepwise Oxidative C–C Coupling and/or C–N Fusion of Zn(II) meso-Pyridin-2-ylthio-porphyrins |
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