Click Access to a Cyclodextrin-Based Spatially Confined AIE Material for Hydrogenase Recognition

Abstract

The spatial confinement of conjugated phenyl rotators is a compulsory requirement for the fluorescence enhancement of aggregation induced emission (AIE) molecules. This work reports a novel spatially confined AIE material by restricting several tetraphenylethylene (TPE) molecules around the primary face of β-cyclodextrin (CD) via a Cu(I) catalytic 1,3-dipolar cycloaddition reaction (click chemistry). The spatial confinement effect was found to significantly enhance the fluorescence emission when compared with a single TPE modified CD. In addition, the emission maxima took place with the dimethyl sulfoxide volume ratio of 30% in a water mixture, which is remarkably different from traditional AIE molecules. Benefiting from the CD’s complexation effect, this material exhibits a selective fluorescence quenching property in certain hydrogenases and can be used as a fluorescence probe for hydrogenase sensing. This demonstrates the potential of the spatially confined AIECD for practical applications.

Sugar-Based Aggregation-Induced Emission Luminogens: Design, Structures, and Applications

“…For example, TPE modified cyclodextrin was prepared and applied in the specific detection of hydrogenase by Wang's group. 174 As shown in Figure 55, seven TPE molecules were modified around the primary face of β-CD to form 63 via Cu(I) catalyzed click reaction. 63 emitted strong blue fluorescence in the mixture of DMSO/ water with 30% of water.…”

“…Besides the host–guest interactions between TPE derivative and cyclodextrin, enzyme fluorescent probe also could be designed based on the specific host–guest interaction between cyclodextrin and enzyme itself. For example, TPE modified cyclodextrin was prepared and applied in the specific detection of hydrogenase by Wang’s group . As shown in Figure , seven TPE molecules were modified around the primary face of β-CD to form 63 via Cu­(I) catalyzed click reaction.…”