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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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本文引用的文献

1
Synthesis of a strapped calix[4]pyrrole: structure and anion binding properties.
Angew Chem Int Ed Engl. 2002 May 17;41(10):1757-9. doi: 10.1002/1521-3773(20020517)41:10<1757::aid-anie1757>3.0.co;2-0.
4
Quantitative evaluation of anion-pi interactions in solution.
Angew Chem Int Ed Engl. 2008;47(22):4114-8. doi: 10.1002/anie.200800636.
5
Strapped and other topographically nonplanar calixpyrrole analogues. Improved anion receptors.
Chem Commun (Camb). 2008 Jan 7(1):24-34. doi: 10.1039/b713183f.
6
Anion receptors based on organic frameworks: highlights from 2005 and 2006.
Chem Soc Rev. 2008 Jan;37(1):151-90. doi: 10.1039/b715825d. Epub 2007 Nov 14.
7
Anion-pi interactions.
Chem Soc Rev. 2008 Jan;37(1):68-83. doi: 10.1039/b614208g. Epub 2007 Sep 12.
9
Calix[4]pyrrole as a chloride anion receptor: solvent and countercation effects.
J Am Chem Soc. 2006 Sep 20;128(37):12281-8. doi: 10.1021/ja064012h.
10

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