用带有显色二吡咯基喹喔啉的杯[4]吡咯对阴离子进行选择性传感。
Selective sensing of anions with calix[4]pyrroles strapped with chromogenic dipyrrolylquinoxalines.
作者信息
Yoo Jaeduk, Kim Min-Soo, Hong Seong-Jin, Sessler Jonathan L, Lee Chang-Hee
机构信息
Department of Chemistry and Institute of Basic Science, Kangwon National University, Chun-Chon 200-701 Korea.
出版信息
J Org Chem. 2009 Feb 6;74(3):1065-9. doi: 10.1021/jo802059c.
Abstract
New calix[4]pyrroles bearing dipyrrolylquinoxaline as strapping elements have been synthesized and characterized by spectroscopic means. The binding behavior of these receptors at 25 degrees C was investigated first by proton NMR spectroscopy in CD(3)CN/DMSO-d(6) (9:1 v/v), as well as by UV-vis spectroscopy and isothermal titration calorimetry (ITC) in CH(3)CN/DMSO (97:3 v/v). The receptors displayed a selective colorimetric response when exposed to the fluoride, dihydrogen phosphate, and acetate anions (studied in the form of the corresponding tetrabutylammonium salts) and an enhanced affinity as compared to a comparable calix[4]pyrrole system lacking the dipyrrolylquinoxaline-containing strap.
摘要
已合成了带有二吡咯基喹喔啉作为束缚单元的新型杯[4]吡咯，并通过光谱手段对其进行了表征。首先在CD(3)CN/DMSO-d(6)（9:1 v/v）中通过质子核磁共振光谱，以及在CH(3)CN/DMSO（97:3 v/v）中通过紫外可见光谱和等温滴定量热法（ITC）研究了这些受体在25℃时的结合行为。当暴露于氟离子、磷酸二氢根离子和醋酸根离子（以相应的四丁基铵盐形式研究）时，这些受体表现出选择性比色响应，并且与缺乏含二吡咯基喹喔啉链的类似杯[4]吡咯体系相比，亲和力增强。
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2
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Chemistry. 2008;14(26):7822-7. doi: 10.1002/chem.200800899.
3
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