Cucurbit[8]Uril‐Stabilized Charge Transfer: An Efficient Supramolecular Approach Toward a Heterogeneous Organic Photocatalyst for Aerobic Oxidation Reactions
Year: 2024
Type: article
Abstract: Host‐stabilized charge transfer (HSCT) has been widely utilized in macrocycle‐derived supramolecular assemblies and architectures. However, there has been less research attention focused on the direct fabrication of pure organic photocatalysts using HSCT. Herein, four viologen derivatives ( m ‐PV 2+ , m ‐BPV 2+ , d ‐PV 2+ , and d ‐BPV 2+ ) with different electron donor‐acceptor (D−A) structures were synthesized. Their host‐guest complexes with cucurbit[8]uril (Q[8]) in an aqueous solution could be switched using the substituted electron donor moieties, in which the host‐guest complexes of m ‐BPV 2+ @Q[8] and d ‐BPV 2+ @Q[8] exhibited HSCT interactions. Control experiments revealed that the d ‐BPV 2+ @Q[8] complex had the strongest ability to sensitize singlet oxygen ( 1 O 2 ). This was ascribed to the increased π‐conjugation of d ‐BPV 2+ @Q[8] , which led to more effective HSCT upon encapsulation by the Q[8] host. Consequently, the d ‐BPV 2+ @Q[8] complex could be easily employed as a heterogeneous photocatalyst for the photooxidation reaction of thioether com‐pounds with high selectivity. In particular, d ‐BPV 2+ @Q[8] was successfully applied to the synthesis of sulfoxide drugs, such as the con‐version of inexpensive Iberverin ($7.0 per gram) to the expensive bioactive inhibitor Iberin ($19500.0 per gram) in high yield (94 %).
Source: Chemistry - A European Journal
Authors: Yi Luo, Haigen Nie, Cuijuan Zou, Yan Fan, Xin‐Long Ni
Institution: Hunan Normal University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
Award: G842102210
OpenAlex ID: W4405231498