Acta Phys. -Chim. Sin. ›› 2016, Vol. 32 ›› Issue (3): 683-690.doi: 10.3866/PKU.WHXB201512302

• ARTICLE • Previous Articles     Next Articles

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

Sha GAO,Wen-Bo LAN,Ying-Wu LIN,Li-Fu LIAO,Chang-Ming NIE*()   

  • Received:2015-11-10 Published:2016-03-04
  • Contact: Chang-Ming NIE E-mail:niecm196132@163.com
  • Supported by:
    the National Natural Science Foundation of China(11275090);Natural Science Foundation of Hunan Province, China(12JJ9006, 2015JJ1012);Scientific Research Fund of Hunan Provincial Education Department, China(12A116)

Abstract:

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.

Key words: Density functional theory, Uranyl-salophen, α, β-Unsaturated carbonyl compound, Molecular recognition

MSC2000: 

  • O641