Click-modified hexahomotrioxacalix[3]arenes as fluorometric and colorimetric dual-modal chemosensors for 2,4,6-trinitrophenol

Chong Wu; Jiang-Lin Zhao; Xue-Kai Jiang; Xin-Long Ni; Xi Zeng; Carl Redshaw; Takehiko Yamato

doi:10.1016/j.aca.2016.06.045

Click-modified hexahomotrioxacalix[3]arenes as fluorometric and colorimetric dual-modal chemosensors for 2,4,6-trinitrophenol

Anal Chim Acta. 2016 Sep 14:936:216-21. doi: 10.1016/j.aca.2016.06.045. Epub 2016 Jun 30.

Authors

Chong Wu¹, Jiang-Lin Zhao¹, Xue-Kai Jiang¹, Xin-Long Ni², Xi Zeng², Carl Redshaw³, Takehiko Yamato⁴

Affiliations

¹ Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga 840-8502, Japan.
² Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China.
³ Department of Chemistry, The University of Hull, Cottingham Road, Hull, Yorkshire, HU6 7RX, UK.
⁴ Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga 840-8502, Japan. Electronic address: yamatot@cc.saga-u.ac.jp.

PMID: 27566358
DOI: 10.1016/j.aca.2016.06.045

Abstract

A new type of chemosensor-based approach to the detection of 2,4,6-trinitrophenol (TNP) is described in this paper. Two hexahomotrioxacalix[3]arene-based chemosensors 1 and 2 were synthesized through click chemistry, which exhibited high binding affinity and selectivity toward TNP as evidenced by UV-vis and fluorescence spectroscopy studies. (1)H NMR titration analysis verified that CH⋯O hydrogen bonding is demonstrated as the mode of interaction, which possibly facilitates effective charge-transfer.

Keywords: 2,4,6-Trinitrophenol; Click chemistry; Colorimetric chemosensor; Fluorometric chemosensor; Hexahomotrioxacalix[3]arene.