Fluorescent calix[4]arene chemosensor for acidic and basic amino acids in pure aqueous media

被引:10
作者
Xu, Yao-Wei [1 ]
Tan, Li-Lin [1 ]
Liu, Jun-Min [1 ]
Xiao, Li-Min [3 ]
Li, Shao-Yong [2 ]
Su, Cheng-Yong [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, State Key Lab Optoelect Mat & Technol, MOE Lab Bioinorgan & Synthet Chem KLGHEI Environm, Guangzhou 510275, Guangdong, Peoples R China
[2] Tianjin Med Univ, Sch Pharm, Basic Med Res Ctr, Tianjin Key Lab Technol Enabling Dev Clin Therape, Tianjin 300070, Peoples R China
[3] Beihang Univ, Sch Comp Sci & Engn, Beijing 100191, Peoples R China
关键词
HIGHLY SELECTIVE FLUORESCENT; RECOGNITION; COMPLEXATION; CALIXARENES; DERIVATIVES;
D O I
10.1039/c4ra04074k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A modified calix[4]arene based receptor 2, conjugated with four bithiophene-cyanoacrylic acid groups, not only recognizes acidic amino acids (Asp and Glu) by quenching fluorescence, but also shows highly selective sensing for basic amino acids (Lys and Arg) by turning on fluorescence in sodium phosphate buffer solution without any organic solvent. The UV-Vis spectroscopy binding analysis and ESI-MS studies indicate that the above complexes have a 1:1 stoichiometry. H-1 NMR and molecular modeling studies suggest a supramolecular complex structure like the relationship between a lid and cup, but not a typical host-guest relationship of the cavity. A plausible mechanism involving intramolecular charge transfer (ICT) is proposed.
引用
收藏
页码:28046 / 28051
页数:6
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