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Covalent Porphyrin Hybrids Linked with Dipyrrin, Bidipyrrin or Thiacorrole

Novel meso-meso directly linked porphyrin hybrids were successfully targeted and synthesized, with porphyrin units linked with dipyrrin, bidipyrrin or thiacorrole, expanding the ranges of dipyrrin derivatives and showing diverse metal coordinations and further influencing the chemical shift of pyrro...

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Detalles Bibliográficos
Autores principales: He, Renbao, Yue, Huan, Kong, Jiahui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151592/
https://www.ncbi.nlm.nih.gov/pubmed/28832543
http://dx.doi.org/10.3390/molecules22091400
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author He, Renbao
Yue, Huan
Kong, Jiahui
author_facet He, Renbao
Yue, Huan
Kong, Jiahui
author_sort He, Renbao
collection PubMed
description Novel meso-meso directly linked porphyrin hybrids were successfully targeted and synthesized, with porphyrin units linked with dipyrrin, bidipyrrin or thiacorrole, expanding the ranges of dipyrrin derivatives and showing diverse metal coordinations and further influencing the chemical shift of pyrrole units. The porphyrinyl dipyrrin nickel complex 3 was successfully obtained in a high yield by the oxidation of porphyrinyl dipyrromethane 2 and subsequent coordination. Further oxidative coupling reactions of 3 afforded por-bidipyrrin-por hybrid 4. Interestingly, an unexpected methoxy por-bidipyrrin-por hybrid 6 was generated by treating 4 with FeCl(3) in CH(2)Cl(2)/MeOH and subsequent coordination. In addition to open chain hybrids, an aromatic scaffold hybrid por-thiacorrole-por 8 was synthesized by treating porphyrinyl dibromo-dipyrrin nickel complex 7 with Na(2)S·9H(2)O. A series of porphyrin hybrids offers a new approach for π-conjugated molecules.
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spelling pubmed-61515922018-11-13 Covalent Porphyrin Hybrids Linked with Dipyrrin, Bidipyrrin or Thiacorrole He, Renbao Yue, Huan Kong, Jiahui Molecules Article Novel meso-meso directly linked porphyrin hybrids were successfully targeted and synthesized, with porphyrin units linked with dipyrrin, bidipyrrin or thiacorrole, expanding the ranges of dipyrrin derivatives and showing diverse metal coordinations and further influencing the chemical shift of pyrrole units. The porphyrinyl dipyrrin nickel complex 3 was successfully obtained in a high yield by the oxidation of porphyrinyl dipyrromethane 2 and subsequent coordination. Further oxidative coupling reactions of 3 afforded por-bidipyrrin-por hybrid 4. Interestingly, an unexpected methoxy por-bidipyrrin-por hybrid 6 was generated by treating 4 with FeCl(3) in CH(2)Cl(2)/MeOH and subsequent coordination. In addition to open chain hybrids, an aromatic scaffold hybrid por-thiacorrole-por 8 was synthesized by treating porphyrinyl dibromo-dipyrrin nickel complex 7 with Na(2)S·9H(2)O. A series of porphyrin hybrids offers a new approach for π-conjugated molecules. MDPI 2017-08-23 /pmc/articles/PMC6151592/ /pubmed/28832543 http://dx.doi.org/10.3390/molecules22091400 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
He, Renbao
Yue, Huan
Kong, Jiahui
Covalent Porphyrin Hybrids Linked with Dipyrrin, Bidipyrrin or Thiacorrole
title Covalent Porphyrin Hybrids Linked with Dipyrrin, Bidipyrrin or Thiacorrole
title_full Covalent Porphyrin Hybrids Linked with Dipyrrin, Bidipyrrin or Thiacorrole
title_fullStr Covalent Porphyrin Hybrids Linked with Dipyrrin, Bidipyrrin or Thiacorrole
title_full_unstemmed Covalent Porphyrin Hybrids Linked with Dipyrrin, Bidipyrrin or Thiacorrole
title_short Covalent Porphyrin Hybrids Linked with Dipyrrin, Bidipyrrin or Thiacorrole
title_sort covalent porphyrin hybrids linked with dipyrrin, bidipyrrin or thiacorrole
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151592/
https://www.ncbi.nlm.nih.gov/pubmed/28832543
http://dx.doi.org/10.3390/molecules22091400
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