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

被引：34
|
作者：
Jiang, Jiaxun [1 ]
Feng, Zhiqiang [1 ]
Liu, Baozhen [1 ]
Hu, Chuanjiang [1 ,2 ]
Wang, Yong [1 ]
机构：
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Nanjing Univ, State Key Lab & Coordinat Chem Inst, Nanjing 210093, Jiangsu, Peoples R China
来源：
DALTON TRANSACTIONS | 2013年 / 42卷 / 21期
关键词：
CIRCULAR-DICHROISM; SUPRAMOLECULAR CHIROGENESIS; ABSOLUTE-CONFIGURATION; PORPHYRIN TWEEZER; ZINC PORPHYRINS; INDUCTION; ALCOHOLS; RATIONALIZATION; COORDINATION; DERIVATIVES;
D O I：
10.1039/c3dt50380a
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
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, H-1 NMR and DFT/TDDFT calculations.
引用
收藏
页码：7651 / 7659
页数：9
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