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RESEARCH ARTICLE
Contents Vol 74(4)

Selective Identification of Phenylalanine Using Cucurbit[7,8]uril-Based Fluorescent Probes

Xiao-Xia Li A , Wei-Tao Xu A , Xin-Yu Deng A , Li-Fei Tian A , Ying Huang B C and Zhu Tao https://orcid.org/0000-0002-8313-1430 A C
+ Author Affiliations
- Author Affiliations

A Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China.

B The Engineering and Research Center for Southwest Bio-Pharmaceutical Resources of National Education Ministry of China, Guizhou University, Guiyang 550025, China.

C Corresponding authors. Email: 467992759@qq.com; gzutao@263.net

Australian Journal of Chemistry 74(4) 221-229 https://doi.org/10.1071/CH20029
Submitted: 5 February 2020  Accepted: 24 August 2020   Published: 1 October 2020

Abstract

The interactions of two host–guest inclusion complexes comprised of cucurbit[7]uril (Q[7]) and cucurbit[8]uril (Q[8]) with a derivative of toluidine blue O (TB) have been investigated using 1H NMR and fluorescence spectroscopy. The experimental results revealed that the Q[7] host interacts with a TB molecule to form a 1 : 1 inclusion complex and the Q[8] host interacts with two TB guest molecules to form a 1 : 2 inclusion complex. The inclusion of the TB guest molecule within the Q[7] host gave rise to significant fluorescence enhancement, whereas the inclusion of the TB guest molecule within the Q[8] host resulted in significant fluorescence quenching. Further recognition experiments involving a series of l-α-amino acids revealed that the TB@Q[7] inclusion fluorescence probe exhibits high selectivity for the recognition of phenylalanine via significant fluorescence quenching in an aqueous solution, whereas the TB@Q[8] inclusion fluorescence probe also exhibited high selectivity for phenylalanine recognition via fluorescence enhancement in an aqueous solution.


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