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Synthesis of Novel Heterocyclic Receptors and the Recognition Properties

Author: LiuMingXia
Tutor: ZhangYouMing；WeiTaiBao
School: Northwest Normal University
Course: Inorganic Chemistry
Keywords: thiadiazole phenolic hydroxy cation recognition mercury ion receptor copper ion receptor
CLC: O626
Type: Master's thesis
Year: 2011
Downloads: 76
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Abstract


This paper includes four chapters:1. This one is about the research of cation recognition in recent years, whichcontain the following topica: （i） the principle of molecular recognition, thesignificance of cations recognition; （ii） the structural characteristics of cationsimpact on receptor design; （iii） receptors bearing thiol groups; （ⅳ） receptorsbearing phenolic hydroxy groups; （ⅴ） receptors bearing imino;2. Two simple mercapto thiadiazole‐based sensors were synthesized by aconvenient method. Their UV‐vis spectra were taken in DMSO‐H2O binary andHEPES buffered solutions. The sensing abilities both 1 and 2 toward various metalcations, such as Zn2+, Pb2+, Cd2+, Ni2+, Co2+, Fe3+, Hg2+, Ag+, Ca2+ and Cu2+, wereprimly investigated by UV‐vis spectroscopy. Upon addition of 2 equiv of Hg2+, sensor1 showed obvious changes in UV‐vis spectrum. Therefore, sensor 1 had a betterselectivity to Hg2+. Pleasantly, sensor 1 still could work well in aqueous solutioncontaining less than 30% organic solvent. By UV‐vis titration experiments, sensors 1and 2 reacted with Hg2+ to form stable complexes and the association constants Ka were4.4×104 M‐1 and 1.0×103 M-1. In （9.5:0.5, v/v） DMSO/H2O HEPES （10 mM） bufferedsolutions at pH 7.20 for sensors 1 and 2. As a result, similar spectroscopic variationof the absorption band was found as above aqueous solutions. It should also benoted that the pH of the solution did not change during these experiments, clearlyexcluding any pH effects.3. Two novel colorimetric cation sensor bearing phenol, thiol and HC=N groupswas designed and synthesized. In a DMSO/H2O （9:1, v/v） solution, the sensorexhibited highly selective recognition of Cu2+ among a range of metal ions tested. Inthe presence of Cu2+, solutions of the sensor underwent a dramatic color changefrom colorless to yellow, while the presence of other metal cations such as Zn2+,Pb2+, Cd2+, Ni2+, Co2+, Fe3+, Hg2+, Ag+ and Ca2+ had no effect on the color. Thedetection limit of the sensor toward Cu2+ is 8.0×10‐7 M and an association constantKa of 4.3×105 M‐1 was measured. The sensing of Cu2+ by this sensor was found to be reversible, with the Cu2+‐induced color being lost upon addition of EDTA.4. Two simple N‐phenyl‐ N′‐（2‐acetoxybenzoyl） urea derivates were sythesized.In a DMSO/H2O （9:1, v/v） solution, the sensors exhibited highly selectiverecognition of Cu2+ among a range of metal ions tested. While the presence of othermetal cations such as Zn2+, Pb2+, Cd2+, Ni2+, Co2+, Fe3+, Ag+ , Ca2+ and Cu2+ had nosuch a change. By UV‐vis titration experiments, sensors reacted with Hg2+ to formstable complexes. The detection limit of the sensor toward Hg2+ is up to 10‐6.Moreover, these compounds on plant growth have some regulatory role.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Heterocyclic compounds
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