Citation: GAO Sha, LAN Wen-Bo, LIN Ying-Wu, LIAO Li-Fu, NIE Chang-Ming. Molecular Recognition of α,β-Unsaturated Carbonyl Compounds and Chiral Guests by Uranyl-Salophen Receptors[J]. Acta Physico-Chimica Sinica, ;2016, 32(3): 683-690. doi: 10.3866/PKU.WHXB201512302 shu

Molecular Recognition of α,β-Unsaturated Carbonyl Compounds and Chiral Guests by Uranyl-Salophen Receptors

1.
School of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, Hunan Province, P. R. China

Corresponding author: NIE Chang-Ming,
Received Date: 10 November 2015
Available Online: 29 December 2015
Fund Project: 国家自然科学基金(11275090) (11275090)湖南省自然科学基金(12JJ9006,2015JJ1012) (12JJ9006,2015JJ1012)湖南省教育厅科学研究基金(12A116)资助项目 (12A116)

Based on density functional theory (DFT) calculations, the molecular recognition of α,β-unsaturated carbonyl compounds and chiral molecules by uranyl-salophen receptors was investigated theoretically. The results showed that the U atom of the receptors was coordinated by the O3 atom of the guests, and the binding energies between receptors and guests increased with the enlargement of the aromatic substituent of the uranylsalophen receptors. In addition, the U―O3 coordination bonds of R₂-and R₃-series complexes are more stable than those of R₁-series complexes, and the conjugation between the C＝C and C＝O bonds of the α,β-unsaturated carbonyl compounds in the coordination complexes was weakened. Moreover, according to circular dichroism (CD) spectra and binding-energy calculations, the molecular-recognition selectivity of an asymmetrical pyrenyl uranyl-salophen (receptor 3) for (R)-1-(2-naphthyl)ethylamine was much higher than that for (S)-1-(2-naphthyl)ethylamine. These results shed new light on the recognition ability of asymmetric uranyl-salophens.
- Density functional theory,
- Uranyl-salophen,
- α,β-Unsaturated carbonyl compound,
- Molecular recognition
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