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

Jascha Melomedov, Anica Wünsche Von Leupoldt, Michael Meister, Frederic Laquai, Katja Heinze*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

New trans-AB2C meso-substituted porphyrin amino acid esters with meso-substituents of tunable electron withdrawing power (B = mesityl, 4-C 6H4F, 4-C6H4CF3, C 6F5) 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 Zn2-4d and Zn1Zn2-4d 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 -C 6H4-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.

Original languageEnglish (US)
Pages (from-to)9727-9739
Number of pages13
JournalDalton Transactions
Volume42
Issue number26
DOIs
StatePublished - Jul 14 2013

ASJC Scopus subject areas

  • Inorganic Chemistry

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