A pH-responsive molecular capsule with an acridine shell: catch and release of large hydrophobic compounds

作者:Kishimoto Mai; Kondo Kei; Akita Munetaka; Yoshizawa Michito*
来源:Chemical communications, 2017, 53(8): 1425-1428.
DOI:10.1039/c6cc09094j

摘要

Unlike common polyaromatic hydrocarbons, acridine is a characteristic compound bearing both pi-stackable large surfaces and a protonable nitrogen atom. Here we report the first synthesis of a supramolecular capsule with multiple acridine panels. In water, the assembly and disassembly of the capsule reversibly occur under neutral and acidic conditions, respectively (>= 10 cycles). Notably, the pH-responsive capsule encapsulates a variety of large hydrophobic compounds (up to 1.6 nm in diameter) such as coumarins, metallophthalocyanines and subphthalocyanine in neutral water and subsequently releases them by simple addition of acid.

  • 出版日期2017