Efficient Fenton Degradation of Perylene Diimide Dye Promoted by a Catalytic Amount of Cucurbit[8]uril

Abstract

Herein, we propose a new method for promoting the degradation of a perylene diimide (PDI) dye, through a Fenton reaction with cucurbit[8]­uril (CB[8]) as a supramolecular catalyst. The CB[8] can encapsulate the hydrophobic moiety of the PDI dye and inhibit its aggregation in aqueous solutions, thus increasing the collision frequency between the PDI and oxidants to accelerate the reaction. As a result, the encapsulated PDI molecule is preferentially degraded, followed by freeing the cavity of CB[8] and enabling it to encapsulate another PDI molecule to realize a catalytic cycle. Hence, a catalytic amount of CB[8] is sufficient to accelerate the the Fenton degradation. It is anticipated that this work will extend the realm of supramolecular catalysis systems and enrich the field of degradation of polycyclic aromatic dyes.

Cucurbit[n]urils for Supramolecular Catalysis

“…Besides inhibiting the reactions of guest groups,t he steric hindrance of CB[n]c an also break the self-aggregation of guests to enhance their reactivity.X ua nd co-workers have reported aC B [8] catalyzedo xidative degradation of ad erivative of perylened iimide (HDPDI) by breaking its aggregates [53] ( Figure 13). Perylene diimide is one of commond yes with large aromatic conjugation.…”

“…The CB[8] catalyzed oxidative degradation of HDPDIbyb reaking the aggregates of HDPDI. Reproduced from ref [53]…”

Fabrication of a Nanoporous Silica Hydrogel by Cross-Linking of SiO2–H3BO3–Hexadecyltrimethoxysilane for Excellent Adsorption of Azo Dyes from Wastewater

“…16 It is necessary to eliminate azo dyes from wastewater to reduce the worldwide water problems faced by society. In recent days, different procedures have been initiated to eliminate the azo dyes, such as photocatalytic degradation, 17−19 Fenton degradation, 20,21 precipitation, 22 membrane separation, 23 and adsorption. 24,25 Compared with the aforementioned processes, adsorption has been considered a promising technology in industrial wastewater treatment because of its advantages, such as the simple fabrication method, low consumption of energy, high efficiency, and relatively low operating cost.…”

“…It is necessary to eliminate azo dyes from wastewater to reduce the worldwide water problems faced by society. In recent days, different procedures have been initiated to eliminate the azo dyes, such as photocatalytic degradation, − Fenton degradation, , precipitation, membrane separation, and adsorption. , Compared with the aforementioned processes, adsorption has been considered a promising technology in industrial wastewater treatment because of its advantages, such as the simple fabrication method, low consumption of energy, high efficiency, and relatively low operating cost. − Numerous adsorbents, namely, activated carbons, , nanometal oxides, , zeolites, , nanoporous silica hydrogels , and graphene oxides, , have been developed to remove contaminants from wastewater. However, the high manufacturing cost and complexities in recycling significantly limited their applications.…”

Concepts and principles of self-n-doping in perylene diimide chromophores for applications in biochemistry, energy harvesting, energy storage, and catalysis

“…[89][90][91][92][93][94][95][96][97][98][99][100][101] Selfassembly of N-PDIs has also been studied extensively, with aggregation into supramolecular structures being controlled with temperature differences, pH adjustment, metallic directing groups, and structural modifications. [102][103][104][105][106][107][108][109][110][111] Many of these phenomena have been reviewed elsewhere. 112 Additionally, many N-PDIs are amphiphilic mesogens capable of forming lyotropic liquid crystal mesophases and have been investigated for use in optical applications.…”