Cis/trans Fluorescent Recognition by Naphthalimide Dyes ⊂ CB [7] Assembly

J Fluoresc. 2016 Jul;26(4):1219-24. doi: 10.1007/s10895-016-1807-2. Epub 2016 Apr 29.

Abstract

A novel method to recognize cis/trans isomers was studied here. The naphthalimide dye as guest could bind with host cucurbit [7]uril (CB [7]) and 1:1 naphthalimide dye ⊂ CB [7] assembly was formed. Moreover, this assembly was used as a fluorescent probe to recognized Fumaric acid (FA) and maleic acid (MA) via fluorescence titration. Two carboxyls in MA are in the same side, they could form stable interaction with the assembly and the fluorescence intensity decreased obviously when naphthalimide dye ⊂ CB [7] was titrated by MA (nearly quenched in 1.5 equiv). But two carboxyls in FA are in opposite sides, the interaction between FA and the assembly was weak and not stable, and the fluorescence intensity changed inconspicuously when the assembly was titrated by FA.

Keywords: CB [7]; Cis/trans recognition; Fluorescent titration; Naphthalimide dye.