title: A pH-responsive molecular capsule with an acridine shell: catch and release of large hydrophobic compounds.
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.
authors.affiliation: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan. yoshizawa.m.ac@m.titech.ac.jp.
authors.forename: Mai
authors.initials: M
authors.lastname: Kishimoto
authors.affiliation: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan. yoshizawa.m.ac@m.titech.ac.jp.
authors.forename: Kei
authors.initials: K
authors.lastname: Kondo
authors.affiliation: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan. yoshizawa.m.ac@m.titech.ac.jp.
authors.forename: Munetaka
authors.initials: M
authors.lastname: Akita
authors.affiliation: Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan. yoshizawa.m.ac@m.titech.ac.jp.
authors.forename: Michito
authors.identifier: http://orcid.org/0000-0002-0543-3943
authors.initials: M
authors.lastname: Yoshizawa