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Structural and Photophysical Characterization of All Five Constitutional Isomers of the Octaethyl-ß,ß'-dioxo-bacterio- and -isobacteriochlorin Series.
Brückner, Christian; Chaudhri, Nivedita; Nevonen, Dustin E; Bhattacharya, Sayantan; Graf, Arthur; Kaesmann, Elizabeth; Li, Ruoshi; Guberman-Pfeffer, Matthew J; Mani, Tomoyasu; Nimthong-Roldán, Arunpatcha; Zeller, Matthias; Chauvet, Adrien A P; Nemykin, Victor.
Afiliación
  • Brückner C; Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, United States.
  • Chaudhri N; Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, United States.
  • Nevonen DE; Department of Chemistry, University of Manitoba Winnipeg, Manitoba, R3T 2 N2, Canada.
  • Bhattacharya S; Department of Chemistry, University of Sheffield Dainton Building, Sheffield, S3 7HF, United Kingdom.
  • Graf A; Department of Chemistry, University of Sheffield Dainton Building, Sheffield, S3 7HF, United Kingdom.
  • Kaesmann E; Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, United States.
  • Li R; Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, United States.
  • Guberman-Pfeffer MJ; Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, United States.
  • Mani T; Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, United States.
  • Nimthong-Roldán A; Department of Chemistry, Youngstown State University One University Plaza, Youngstown, OH 44555-3663, United States.
  • Zeller M; Department of Chemistry, Youngstown State University One University Plaza, Youngstown, OH 44555-3663, United States.
  • Chauvet AAP; Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, United States.
  • Nemykin V; Department of Chemistry, University of Sheffield Dainton Building, Sheffield, S3 7HF, United Kingdom.
Chemistry ; 27(65): 16189-16203, 2021 Nov 22.
Article en En | MEDLINE | ID: mdl-34535932
It is well-known that treatment of ß-octaethylporphyrin with H2 O2 /conc. H2 SO4 converts it to a ß-oxochlorin as well as all five constitutional isomers of the corresponding ß,ß'-dioxo-derivatives: two bacteriochlorin-type isomers (ß-oxo groups at opposite pyrrolic building blocks) and three isobacteriochlorin-type isomers (ß-oxo-groups at adjacent pyrrolic building blocks). By virtue of the presence of the strongly electronically coupled ß-oxo auxochromes, none of the chromophores are archetypical chlorins, bacteriochlorins, or isobacteriochlorins. Here the authors present, inter alia, the single crystal X-ray structures of all free-base diketone isomers and a comparative description of their UV-vis absorption spectra in neutral and acidic solutions, and fluorescence emission and singlet oxygen photosensitization properties, Magnetic Circular Dichroism (MCD) spectra, and singlet excited state lifetimes. DFT computations uncover underlying tautomeric equilibria and electronic interactions controlling their electronic properties, adding to the understanding of porphyrinoids carrying ß-oxo functionalities. This comparative study lays the basis for their further study and utilization.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Porfirinas Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Porfirinas Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Alemania