Jump to main content
Jump to site search


A photo-stable fluorescent chiral thiourea probe for enantioselective discrimination of chiral guests

Author affiliations

Abstract

Herein, a chiral thiourea Schiff base derived from (1R,2R)-1,2-cyclohexanediamine and tetraphenylethylene (TPE) was applied as a highly effective chiral sensor for the enantioselective discrimination of various acids and amines via ion-pair and hydrogen-bond interaction. Compared to the case of the sensors 5 and 6, the additional thiourea and hydrogen groups of sensor 4 were essential and greatly enhanced the enantioselectivity of chiral guests. In addition, for amino acids, the sensor 4 showed high enantioselectivity, and precipitates visible by the naked eye appeared; however, for chiral amines, the enantioselectivity decreased. This was attributed to weaker hydrogen bond interaction between the amino groups of chiral amines and the sensor. Both the thiourea and acidic hydroxyl groups are essential for chiral TPE thiourea to provide an appropriate chiral environment for highly efficient enantioselective discrimination of chiral substrates. Our findings will be of great value in the design of new chiral sensors.

Graphical abstract: A photo-stable fluorescent chiral thiourea probe for enantioselective discrimination of chiral guests

Back to tab navigation

Supplementary files

Publication details

The article was received on 22 Jan 2018, accepted on 30 Jan 2018 and first published on 14 Feb 2018


Article type: Paper
DOI: 10.1039/C8NJ00374B
Citation: New J. Chem., 2018, Advance Article
  •   Request permissions

    A photo-stable fluorescent chiral thiourea probe for enantioselective discrimination of chiral guests

    X. Zhang, Q. Yu, S. Chen and Z. Dai, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ00374B

Search articles by author

Spotlight

Advertisements