Ion-responsive fluorescent compounds VI. Coumarin 153 linked to rigid crowns for improvement of selectivity

被引:38
作者
Leray, I
Habib-Jiwan, JL
Branger, C
Soumillion, JP
Valeur, B
机构
[1] ENS Cachan, CNRS UMR 8531, Lab Photophys & Photochim Supramol & Macromol, Dept Chim, F-94235 Cachan, France
[2] Univ Catholique Louvain, Lab Photochim & Chim Organ Phys, B-1348 Louvain, Belgium
[3] Conservatoire Natl Arts & Metiers, Lab Chim Gen, F-75003 Paris, France
关键词
fluorescence; supramolecular photochemistry; sensors; alkali; alkaline earth metal ion;
D O I
10.1016/S1010-6030(00)00285-9
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The photophysical and complexing properties of fluoroionophores consisting of the coumarin C153 linked to dibenzo-16-crown-5 (C153-DBC) and tribenzo-19-crown-6 (C153-TBC) are described in acetonitrile and ethanol. The carbonyl group of the coumarin moiety is in direct interaction with a bound cation. The selectivity of these compounds for a given alkali or alkaline earth metal ion was found to be better than that of previously reported crowned coumarins owing to the rigidity of dibenzo- and tribenzocrowns. In acetonitrile, a very high selectivity for Ca2+ versus Mg2+ has been found. In ethanol, C153-DBC is selective for Na+ and C153-TBC is selective for K+, as expected from the relative size of the crown cavity. (C) 2000 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:163 / 169
页数:7
相关论文
共 19 条
[1]  
[Anonymous], 1994, TOPICS FLUORESCENCE
[2]   Conformational studies of dibenzo-16-crown-5 lariat ethers [J].
Bartsch, RA ;
Kim, JS ;
Olsher, U ;
Purkiss, DM .
SUPRAMOLECULAR CHEMISTRY, 1996, 6 (3-4) :327-331
[3]   ION-RESPONSIVE FLUORESCENT COMPOUNDS .4. EFFECT OF CATION BINDING ON THE PHOTOPHYSICAL PROPERTIES OF A COUMARIN LINKED TO MONOAZA-CROWN AND DIAZA-CROWN ETHERS [J].
BOURSON, J ;
POUGET, J ;
VALEUR, B .
JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (17) :4552-4557
[4]  
Bourson J, 1994, J Fluoresc, V4, P275, DOI 10.1007/BF01881438
[5]   ION-RESPONSIVE FLUORESCENT COMPOUNDS .3. CATION COMPLEXATION WITH COUMARIN-153 LINKED TO MONOAZA-15-CROWN-5 [J].
BOURSON, J ;
BORREL, MN ;
VALEUR, B .
ANALYTICA CHIMICA ACTA, 1992, 257 (02) :189-193
[6]  
Czarnik A. W., 1992, ACS S SERIES, V538
[7]   Signaling recognition events with fluorescent sensors and switches [J].
de Silva, AP ;
Gunaratne, HQN ;
Gunnlaugsson, T ;
Huxley, AJM ;
McCoy, CP ;
Rademacher, JT ;
Rice, TE .
CHEMICAL REVIEWS, 1997, 97 (05) :1515-1566
[8]  
Desvergne J.P., 1997, NATO ASI SERIES
[9]  
HabibJiwan J.-L., 1998, J PHOTOCH PHOTOBIO A, V116, P127
[10]   SODIUM-ION SENSING BY CELLULOSE TRIACETATE PLASTICIZER MEMBRANE CONTAINING DIBENZO-16-CROWN-5 CHROMOIONOPHORE [J].
HAYASHITA, T ;
KUMAZAWA, M ;
LEE, JC ;
BARTSCH, RA .
CHEMISTRY LETTERS, 1995, (08) :711-712