Issue 4, 2001

Synthesis and sensing behavior of cyanoanthracene modified 1,3-alternate calix[4]benzocrown-6: a new class of Cs+ selective optical sensors

Abstract

1,3-Calix[4]bis(10-cyano-9-anthrylmethyl-o-benzocrown-6), AnCN2, and 1,3-calix[4]-25,27-bis(allyloxy)-26,28-(10-cyano-9-anthrylmethyl-o-benzocrown-6), AnCN1, were synthesized as the first generation of Cs+ selective optical sensors based on calixarenes. The maximum enhancement in the emission of AnCN2 and AnCN1 upon Cs+ complexation was 11.7 and 8.2 in a 1 ∶ 1 CH2Cl2MeOH mixture. Their response to various alkali metal ions follows the order Cs+ > Rb+ ≫ K+ ≫ Na+ > Li+ indicating good selectivity towards caesium. The fluorescence and absorption profile for Cs+ complexation suggest a 1 ∶ 1 stoichiometry for the host AnCN1–Cs complex and a stability constant of 107 M−1. AnCN2, on the other hand, shows two plateau regions corresponding to a 1 ∶ 2 stoichiometry for complexation of Cs+. The first complexation constant is much higher (107 M−1) than the second one (104 M−1). The NMR studies further substantiate the complexation of two metal ions by AnCN2. This is the first report of stepwise complexation of metal ions to a 1,3-alternate calix[4]bis(crown-6) derivative.

Graphical abstract: Synthesis and sensing behavior of cyanoanthracene modified 1,3-alternate calix[4]benzocrown-6: a new class of Cs+ selective optical sensors

Article information

Article type
Paper
Submitted
15 Sep 2000
Accepted
09 Feb 2001
First published
19 Mar 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 585-591

Synthesis and sensing behavior of cyanoanthracene modified 1,3-alternate calix[4]benzocrown-6: a new class of Cs+ selective optical sensors

H. Ji, R. Dabestani, G. M. Brown and R. L. Hettich, J. Chem. Soc., Perkin Trans. 2, 2001, 585 DOI: 10.1039/B007507H

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