Differentiation of cis- and trans-isomers of the novel napthalene-aza receptor by naked-eye colorimetric anion sensing

作者：Thangadurai T Daniel; Chung Gyusung; Kwon Ohyun; Jin Dongri; Lee Yong Ill^*

来源：Tetrahedron Letters, 2011, 52(48): 6465-6469.

DOI：10.1016/j.tetlet.2011.09.103

• Isomers
• Urea
• Anions
• Colorimetric sensors
• Fluorescence
• Photoinduced electron transfer

Novel chromofluorogenic receptors 1 (cis-isomer) and 2 (trans-isomer) were developed using an aza-nitro-phenyl group as a chromophore, urea moiety as a binding unit, and naphthalene as a fluorophore. The position of nitro-phenyl moiety in the chromophores influences the naked-eye colorimetric anion sensing which differentiates the geometrical isomers. Receptor 2 showed sensitivity toward F- than HP2O73- and its fluorescence emission (lambda(max) = 370 nm) was significantly 'switched-off' at art excitation wavelength of 260 nm in CH3CN:DMSO (90: 10, v/v) solution at 25 degrees C. The fluorescence titration experimental results revealed that the receptor 2 binds strongly with F- than HP2O73- ions in 1:1 stoichiometry. The quantum mechanical calculations through time dependant density functional theory (TD-DFT) using basis set B3LYP/6-31G(d) supported our experimental findings agreeably.

• 出版日期2011-11-30
• 单位延边大学