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   

  1. 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 出版日期:2015-05-25 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   

  1. 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 Online:2015-05-25 Published:2015-01-06
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21161005).

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 (Ka>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