Synthesis, Recognition and Sensing Properties for Anions Based on a Carbazole Derivative Containing Phenylaminothiourea Units

doi:10.6023/cjoc201410030

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (5): 1069-1074.DOI: 10.6023/cjoc201410030 Previous Articles Next Articles

ARTICLE

含苯胺基硫脲单元的咔唑衍生物的合成及其对阴离子的识别传感研究

蹇军友, 闫柏任, 潘顶伍, 谭赞, 吕新阳, 杜欢, 鲍小平

贵州大学精细化工研究开发中心绿色农药与农业生物工程国家重点实验室培育基地教育部绿色农药与农业生物工程重点实验室贵阳 550025

收稿日期:2014-10-22 修回日期:2014-12-10 发布日期:2015-01-06
通讯作者: 鲍小平 E-mail:baoxp_1980@aliyun.com
基金资助:
国家自然科学基金(No.21161005)资助项目.

Synthesis, Recognition and Sensing Properties for Anions Based on a Carbazole Derivative Containing Phenylaminothiourea Units

Jian Junyou, Yan Boren, Pan Dingwu, Tan Zan, Lü Xinyang, Du Huan, Bao Xiaoping

Center for Research and Development of Fine Chemicals, State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025

Received:2014-10-22 Revised:2014-12-10 Published:2015-01-06
Supported by:
Project supported by the National Natural Science Foundation of China (No.21161005).

1. Synthesis, Recognition and Sensing Properties for Anions Based on a Carbazole Derivative Containing Phenylaminothiourea Units.PDF(803KB)

Abstract

A carbazole-based anion receptor (L) containing phenylaminothiourea recognition units was designed and synthesized using carbazole as starting compound, and its structure was characterized by ¹H NMR, ¹³C NMR, MS, IR and elemental analysis. UV-Vis and fluorescence titration experiments indicated that L selectively recognized F^-, AcO^- and H₂PO₄^- in DMSO, showing strong interactions (K_a>10⁴ L/mol) with these three anions. During the anion recognition process, a naked-eye de-tectable color change and a distinct fluorescence quenching of L were simultaneously observed, indicative of its potential as colorimetric and fluorescent sensors for anions. Interestingly, only F^- and AcO^- could be recognized by L in DMSO containing 10% (V/V) H2O; a specific recognition of L towards AcO^- was realized in DMSO containing 20% (V/V) H2O.

Key words: phenylaminothiourea, carbazole, hydrogen bond, anion recognition, sensing

Cite this article

Jian Junyou, Yan Boren, Pan Dingwu, Tan Zan, Lü Xinyang, Du Huan, Bao Xiaoping. Synthesis, Recognition and Sensing Properties for Anions Based on a Carbazole Derivative Containing Phenylaminothiourea Units[J]. Chin. J. Org. Chem., 2015, 35(5): 1069-1074.

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含苯胺基硫脲单元的咔唑衍生物的合成及其对阴离子的识别传感研究

Synthesis, Recognition and Sensing Properties for Anions Based on a Carbazole Derivative Containing Phenylaminothiourea Units

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