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Studies on Tetrathiafulvalene-Based Ion Sensors

Author: LiuLianWei
Tutor: LiXiaoChuan；ZhaoBangTun
School: Henan Normal
Course: Organic Chemistry
Keywords: tetrathiafulvalene ion recognition sensor
CLC: TP212.2
Type: Master's thesis
Year: 2011
Downloads: 53
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Abstract


Tetrathiafulvalene （TTF） and its derivatives have been extensively applied to the research of ion sensors, since they have special redox and strong electron-donating properties. Exploiting TTF-based redox-switchable ligands for ion recognition has been one of the focuses of recent research. To date the TTF-based sensors is mainly constructed by associating a binding unit to the electroactive TTF framework, such as crown-ether, thiacrown ethers, azacrown ether, amide bond, pyridyl and so on. It could recognize ions by measuring electrooptic signal induced by interaction between ions and binding unit. In order to develop new ion sensors, we synthesized three series of tetrathiafulvalene derivatives through introducing different binding units to TTF skeleton, and studied their characteristics of ion recognition. The research results are as follows:1. A series of tetrathiafulvalene-ferrocene derivatives were designed and synthesized, and their chemical structures were characterized by 1H-NMR, 13C-NMR, FAB or MALDI-TOF Mass spectra, IR and elementary analysis. Because TTF and ferrocene are well-established electroactive unit, The identification properties of target compounds toward cations and anions were evaluated by cyclic voltammetry （CV）. The results showed that although the target compounds could not act as dual electrochemical recognition sensors, compound 10b has high affinity towards Zn2+, Cd2+ and Cl-, and could be taken as a excellent electrochemical sensor.2. A new tetrathiafulvalene-quinoline dyad was synthesized using the method of“Click”reaction and characterized by 1H-NMR, 13C-NMR, FAB or MALDI-TOF Mass spectra, IR and elementary analysis. The recognition properties of target compounds for cations were investigated using different methods including and cyclic voltammetry, 1H NMR titration and fluorescence titration. The electrochemical detection indicates that the target compound 17 is able to electrochemically respond in the presence of Zn2+. Fluorescence titration experiment demonstrates that the fluorescence emission intensity of receptor 17 was dramatically increased when Zn2+ or Cd2+ was added, exhibiting high selectivities and recognition capability for Zn2+ and Cd2+. And 1H NMR titration confirmed the strong complexing ability between compound 17 and Zn2+ or Cd2+. In short, compound 17 could serve as a highly sensitive and selective multisignaling optical-electrochemical Zn2+ cation sensor, meanwhile it could be used as a fluorescent probe for Cd2+.3. Two novel tetrathiafulvalene-naphthol derivatives were synthesized and characterized by 1H-NMR, 13C-NMR, FAB or MALDI-TOF Mass spectra, IR and elementary analysis. The properties study of ion recognition is carried out by CV and fluorescence titration. Electrochemical recognition experiments show that compound 18 could identify Ba2+ and it has apparent response to Zn2+ and Cd2+. Fluorescence titration experiment indicates that the fluorescence emission intensity of receptor 18 was increased when detected ions except Ba2+ was added. When Zn2+ or Cd2+ was added, the fluorescence enhancement is more notable. In brief, the target compound 18 could serve for a dual optical-electrochemical chemosensor for alkaline earth metal ion Ba2+, and it could be treated as an optical-electrochemical sensor for transition metal ions Zn2+ and Cd2+.

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CLC: > Industrial Technology > Automation technology,computer technology > Automation technology and equipment > Automation components,parts > Transmitter ( converter),the sensor > Chemical sensors
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