Effect of host–guest complex formation on the fluorescence of 6-methoxy-1-methyl-quinolinium cation with 4-sulfonatocalix[4]arene: utilization as a fluorescent probe for the study of difenzoquat binding

Harangozó, József G. and Miskolczy, Zsombor and Biczók, László and Wintgens, Véronique and Lorthioir, Cédric (2014) Effect of host–guest complex formation on the fluorescence of 6-methoxy-1-methyl-quinolinium cation with 4-sulfonatocalix[4]arene: utilization as a fluorescent probe for the study of difenzoquat binding. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 81 (3-4). pp. 377-384. ISSN 1388-3127

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Abstract

The complexation of the highly fluorescent 6-methoxy-1-methyl-quinolinium (C1MQ) and the widely used herbicide, difenzoquat (DFQ), with 4-sulfonatocalix[4]arene (SCX4) macrocycle was studied by isothermal titration calorimetry, fluorescence and NMR spectroscopy in aqueous solutions at 298 K. Both guests produced 1:1 complexes with SCX4, but the binding affinity of C1MQ was more than one order of magnitude larger than that of DFQ in neutral medium. The higher stability of C1MQSCX4 complex originated from the significant enthalpy gain upon its formation. The encapsulation of C1MQ in SCX4 in the ground state resulted in an efficient fluorescence quenching due to electron transfer from the host to the excited guest. The marked difference in the fluorescence quantum yields for free and bound C1MQ was used to detect the competitive complexation of DFQ in SCX4.

Item Type:	Article
Subjects:	Q Science / természettudomány > QD Chemistry / kémia > QD02 Physical chemistry / fizikai kémia
Depositing User:	Dr. László Biczók
Date Deposited:	21 Sep 2015 13:24
Last Modified:	01 Dec 2015 00:15
URI:	http://real.mtak.hu/id/eprint/27141

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• Effect of host–guest complex formation on the fluorescence of 6-methoxy-1-methyl-quinolinium cation with 4-sulfonatocalix[4]arene: utilization as a fluorescent probe for the study of difenzoquat binding. (deposited 21 Sep 2015 13:24) [Currently Displayed]

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