Chem. J. Chinese Universities ›› 2025, Vol. 46 ›› Issue (5): 20250033.doi: 10.7503/cjcu20250033

• Organic Chemistry • Previous Articles     Next Articles

Photolysis of Photoremovable Protecting Group Molecule Mediated by the Host-guest Interaction of Cucurbit[n]uril

LIU Chong, LIU Simin()   

  1. School of Chemistry and Chemical Engineering,Wuhan University of Science and Technology,Wuhan 430081,China
  • Received:2025-02-04 Online:2025-05-10 Published:2025-02-26
  • Contact: LIU Simin E-mail:liusimin@wust.edu.cn
  • Supported by:
    the National Natural Science Foundation of China(21871216)

Abstract:

An aromatic acridine derivative with photoremovable protecting group(PPG) properties was designed and synthesized. The host-guest recognition process between this guest molecule and cucurbit[n]uril(CB[n], n=7, 8, 10) was investigated, along with the effects of host-guest interaction on the photolysis of the guest in aqueous-phase using nuclear magnetic resonance(NMR), ultraviolet visible(UV-Vis) and fluorescence spectroscopies. The results showed that CB[7] formed a 1׃1 host-guest inclusion complex, while CB[8] formed both 1׃1 and 1׃2 complexes with the guest. Similarly, CB[10] exhibited a 1׃2 binding mode. Furthermore, CB[7] was found to inhibit the photolysis, whereas CB[8] significantly enhanced the photolysis rate of the guest. This study highlights how subtle variations in CB[n] cavity size influence the photolysis reaction, offering insights into the design of CB[n]-based nanoreactor- mediated supramolecular systems for aqueous-phase photolysis of PPG molecules.

Key words: Photoremovable protecting group, Photolysis reaction, Host-guest interaction, Cucurbit[n]uril, Nanoreactor

CLC Number: 

TrendMD: