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Issue 21, 2013
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Chiral recognition of amino acid esters by a novel oxalic amide-linked bisporphyrin

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Abstract

A novel oxalic amide-linked bisporphyrinate 1 has been designed and synthesized, which shows chiral recognition ability for amino acid ethyl esters. The structure of complex 1·(D-Phe-OEt)(L-Phe-OEt) has been solved by X-ray crystallography. It reveals the following information: bisporphyrin unit adopts anti-configuration; compound 1 forms 1 : 2 complex with amino acid ethyl esters; one important hydrogen bond is formed between the coordinated nitrogen of amino acid ester and carbonyl oxygen in the amide group. The chiral recognition mechanism has been further investigated by UV-Vis spectra, 1H NMR and DFT/TDDFT calculations.

Graphical abstract: Chiral recognition of amino acid esters by a novel oxalic amide-linked bisporphyrin

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Publication details

The article was received on 07 Feb 2013, accepted on 06 Mar 2013 and first published on 06 Mar 2013


Article type: Paper
DOI: 10.1039/C3DT50380A
Citation: Dalton Trans., 2013,42, 7651-7659
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    Chiral recognition of amino acid esters by a novel oxalic amide-linked bisporphyrin

    J. Jiang, Z. Feng, B. Liu, C. Hu and Y. Wang, Dalton Trans., 2013, 42, 7651
    DOI: 10.1039/C3DT50380A

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