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A pH-responsive molecular capsule with an acridine shell: catch and release of large hydrophobic compounds†
Mai Kishimoto,Kei Kondo,Munetaka Akita,Michito Yoshizawa
Chemical Communications Pub Date : 01/03/2017 00:00:00 , DOI:10.1039/C6CC09094J
Abstract

Unlike common polyaromatic hydrocarbons, acridine is a characteristic compound bearing both π-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.

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