Porphyrin amino acids-amide coupling, redox and photophysicalproperties of bis(porphyrin) amides

Publication type:
Journal article
Metadata:
Autoren
  • Jascha Melomedov
  • Anica Wunsche von Leupoldt
  • Michael Meister
  • Frederic Laquai
  • Katja Heinze
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000320246200040&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1039/c3dt50711d
eISSN
1477-9234
Externe Identifier
  • Clarivate Analytics Document Solution ID: 162DZ
  • PubMed Identifier: 23685531
ISSN
1477-9226
Ausgabe der Veröffentlichung
26
Zeitschrift
DALTON TRANSACTIONS
Paginierung
9727 - 9739
Datum der Veröffentlichung
2013
Status
Published
Titel
Porphyrin amino acids-amide coupling, redox and photophysicalproperties of bis(porphyrin) amides
Sub types
  • Article
Ausgabe der Zeitschrift
42

Data source: Web of Science (Lite)

Other metadata sources:
Autoren
  • Jascha Melomedov
  • Anica Wünsche von Leupoldt
  • Michael Meister
  • Frédéric Laquai
  • Katja Heinze
DOI
10.1039/c3dt50711d
eISSN
1477-9234
ISSN
1477-9226
Ausgabe der Veröffentlichung
26
Zeitschrift
Dalton Transactions
Sprache
en
Paginierung
9727 - 9727
Datum der Veröffentlichung
2013
Status
Published
Herausgeber
Royal Society of Chemistry (RSC)
Herausgeber URL
http://dx.doi.org/10.1039/c3dt50711d
Datum der Datenerfassung
2024
Titel
Porphyrin amino acids–amide coupling, redox and photophysical properties of bis(porphyrin) amides
Ausgabe der Zeitschrift
42

Data source: Crossref

Abstract
New trans-AB2C meso-substituted porphyrin amino acid esters with meso-substituents of tunable electron withdrawing power (B = mesityl, 4-C6H4F, 4-C6H4CF3, C6F5) were prepared as free amines 3a-3d, as N-acetylated derivatives Ac-3a-Ac-3d and corresponding zinc(II) complexes Zn-Ac-3a-Zn-Ac-3d. Several amide-linked bis(porphyrins) with a tunable electron density at each porphyrin site were obtained from the amino porphyrin precursors by condensation reactions (4a-4d) and mono- and bis(zinc(II)) complexes Zn(2)-4d and Zn(1)Zn(2)-4d were prepared. The electronic interaction between individual porphyrin units in bis(porphyrins) 4 is probed by electrochemical experiments (CV, EPR), electronic absorption spectroscopy, steady-state and time-resolved fluorescence spectroscopy in combination with DFT/PCM calculations on diamagnetic neutral bis(porphyrins) 4 and on respective charged mixed-valent radicals 4(+/-). The interaction via the -C6H4-NHCO-C6H4- bridge, the site of oxidation and reduction and the lowest excited singlet state S1, is tuned by the substituents on the individual porphyrins and the metalation state.
Addresses
  • Johannes Gutenberg-University of Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.
Autoren
  • Jascha Melomedov
  • Anica Wünsche von Leupoldt
  • Michael Meister
  • Frédéric Laquai
  • Katja Heinze
DOI
10.1039/c3dt50711d
eISSN
1477-9234
Externe Identifier
  • PubMed Identifier: 23685531
Open access
false
ISSN
1477-9226
Ausgabe der Veröffentlichung
26
Zeitschrift
Dalton transactions (Cambridge, England : 2003)
Schlüsselwörter
  • Zinc
  • Amides
  • Organometallic Compounds
  • Porphyrins
  • Amino Acids
  • Electron Spin Resonance Spectroscopy
  • Molecular Structure
  • Oxidation-Reduction
  • Quantum Theory
  • Photochemical Processes
Sprache
eng
Medium
Print-Electronic
Online publication date
2013
Paginierung
9727 - 9739
Datum der Veröffentlichung
2013
Status
Published
Datum der Datenerfassung
2013
Titel
Porphyrin amino acids-amide coupling, redox and photophysical properties of bis(porphyrin) amides.
Sub types
  • Research Support, Non-U.S. Gov't
  • Journal Article
Ausgabe der Zeitschrift
42

Data source: Europe PubMed Central

Abstract
New trans-AB2C meso-substituted porphyrin amino acid esters with meso-substituents of tunable electron withdrawing power (B = mesityl, 4-C6H4F, 4-C6H4CF3, C6F5) were prepared as free amines 3a-3d, as N-acetylated derivatives Ac-3a-Ac-3d and corresponding zinc(II) complexes Zn-Ac-3a-Zn-Ac-3d. Several amide-linked bis(porphyrins) with a tunable electron density at each porphyrin site were obtained from the amino porphyrin precursors by condensation reactions (4a-4d) and mono- and bis(zinc(II)) complexes Zn(2)-4d and Zn(1)Zn(2)-4d were prepared. The electronic interaction between individual porphyrin units in bis(porphyrins) 4 is probed by electrochemical experiments (CV, EPR), electronic absorption spectroscopy, steady-state and time-resolved fluorescence spectroscopy in combination with DFT/PCM calculations on diamagnetic neutral bis(porphyrins) 4 and on respective charged mixed-valent radicals 4(+/-). The interaction via the -C6H4-NHCO-C6H4- bridge, the site of oxidation and reduction and the lowest excited singlet state S1, is tuned by the substituents on the individual porphyrins and the metalation state.
Autoren
  • Jascha Melomedov
  • Anica Wünsche von Leupoldt
  • Michael Meister
  • Frédéric Laquai
  • Katja Heinze
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/23685531
DOI
10.1039/c3dt50711d
eISSN
1477-9234
Ausgabe der Veröffentlichung
26
Zeitschrift
Dalton Trans
Schlüsselwörter
  • Amides
  • Amino Acids
  • Electron Spin Resonance Spectroscopy
  • Molecular Structure
  • Organometallic Compounds
  • Oxidation-Reduction
  • Photochemical Processes
  • Porphyrins
  • Quantum Theory
  • Zinc
Sprache
eng
Country
England
Paginierung
9727 - 9739
Datum der Veröffentlichung
2013
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2013
Titel
Porphyrin amino acids-amide coupling, redox and photophysical properties of bis(porphyrin) amides.
Sub types
  • Journal Article
  • Research Support, Non-U.S. Gov't
Ausgabe der Zeitschrift
42

Data source: PubMed

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