Anion Recognition by Artificial Polyamide Receptors

Marcin Pawlak 1Adam Sobczuk 1Jarosław Kalisiak 1Janusz Jurczak 2

1. Polish Academy of Sciences, Institute of Physical Chemistry, Kasprzaka 44/52, Warszawa 01-224, Poland
2. Uniwersytet Warszawski, Wydział Chemii, Warszawa, Poland

Abstract

Synthesis and examination of receptors, which are able to bind different kinds of molecules, are one of the main purposes of supramolecular chemistry [1]. Synthesis of anion receptors is an especially demanding task due to larger size, variety of shapes and low charge density of anions comparing to cations. One of the ways to solve these problems is a design of the tweezer-like receptors which are flexible enough to adjust their structure to guests of various sizes and shapes. An interesting application of anion receptors is formation of optical sensors, especially those able to give visible response in the presence of anions [2].

Simple and efficient way of synthesis of both macrocyclic 1 and open-chained 2 tweezer-like molecules will be presented. Modular structure of this type compounds is easy modifiable and allows to incorporate an array of various groups. Compounds bearing nitro groups change color in the presence of anions. Binding properties of obtained receptors were examined by 1H NMR titrations with three typical anions - Cl-, PhCOO-, and H2PO4-. Binding constants, obtained in DMSO by this method, vary from 10 to 103.

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[1] F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.

[2] K. Choi, A. D. Hamilton, Coord. Chem. Rev. 2003, 240, 101-110.

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Presentation: poster at 18th Conference on Physical Organic Chemistry, Posters, by Marcin Pawlak
See On-line Journal of 18th Conference on Physical Organic Chemistry

Submitted: 2006-06-08 16:34
Revised:   2009-06-07 00:44
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