Synthesis of Fluorescent Molecular Sensory System for Endocrine Disruptors Based on Dansylthiacalix[6]arenes

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Title:Synthesis of Fluorescent Molecular Sensory System for Endocrine Disruptors Based on Dansylthiacalix[6]arenes
Creators:
Toda, Masaya
Kondo, Yoshihiko
Niimi, Tomohiro
Higuchi, Yutaka
Endo, Ken
Hamada, Fumio
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 6, pp. 1381-1394
Uncontrolled Keywords:Thiacalixarenes, Calixarenes, Chlorinated phenols, Receptors, Endocrine disruptors, Fluorescent sensors, 2,4-Dichlorophenoxyacetic acid, Dioxins

Abstract

Flexible fluorescent hosts, mono-, di- and tridansyl-modified <i>tert</i>-butylthiacalix[6]arenes (<strong>TC[6]A-1</strong>, <strong>TC[6]A-2</strong> and <strong>TC[6]A-3</strong>, respectively) and didansyl-<i>tert</i>-butylcalix[6]arene (<strong>C[6]A-2</strong>) have been synthesized in order to investigate their fluorescent chemosensor functionality, which detects endocrine disruptors. The hosts, <strong>TC[6]A-1</strong>, <strong>TC[6]A-2</strong>, <strong>TC[6]A-3</strong> and <strong>C[6]A-2</strong> exhibit pure monomer fluorescence spectra, of which the spectra shows a decrease fluorescence intensity in the presence of guests. The extent of fluorescence variation of <strong>TC[6]A-1</strong>, <strong>TC[6]A-2</strong>, <strong>TC[6]A-3</strong> and <strong>C[6]A-2</strong> upon a guest addition was recognized as the manifestation of sensing ability of the hosts. A sensing parameter (∆<i>I/I</i><sup>0</sup>) was used to describe the sensing ability of four hosts. Host <strong>TC[6]A-2</strong> was able to detect 2,4-dichlorophenoxyacetic acid with high sensitivity. The guest-induced variations in the fluorescence intensities and MM2-minimized structures of the hosts suggest that the appended moieties of the hosts act as a hydrophobic cap and a probe showing the host to form a 1:1 host- guest complex. <p>

Title:Synthesis of Fluorescent Molecular Sensory System for Endocrine Disruptors Based on Dansylthiacalix[6]arenes
Creators:
Toda, Masaya
Kondo, Yoshihiko
Niimi, Tomohiro
Higuchi, Yutaka
Endo, Ken
Hamada, Fumio
Uncontrolled Keywords:Thiacalixarenes, Calixarenes, Chlorinated phenols, Receptors, Endocrine disruptors, Fluorescent sensors, 2,4-Dichlorophenoxyacetic acid, Dioxins
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:6
Page Range:pp. 1381-1394
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041381UNSPECIFIED
ID Code:2280
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Toda, Masaya; Kondo, Yoshihiko; Niimi, Tomohiro; Higuchi, Yutaka; Endo, Ken; Hamada, Fumio (2004) Synthesis of Fluorescent Molecular Sensory System for Endocrine Disruptors Based on Dansylthiacalix[6]arenes. Collection of Czechoslovak Chemical Communications, 69 (6). pp. 1381-1394. ISSN 0010-0765

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