A photochemically activated cyclophane

Seiji Shinkai, Akiko Yoshioka, Hatsumi Nakayama, Osamu Manabe

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)


A water-soluble, photoresponsive macrocycle (1), composed of two N + cations and two azobenzene units, has been synthesized. This cyclophane changes its cavity shape in response to a photoinduced trans-cis isomerization of the azobenzene moieties. The photoresponsive association behaviour has been examined for mono- and di-carboxylate guest molecules through spectral studies, thermal cis→trans isomerization, and electrical conductance measurements. It has been shown that cis-(1) strongly binds guest molecules having a general structure -OOC(CH2) nCOO-, the driving force for the guest binding being the electrostatic force between two N+ cations and two carboxylate anions and the hydrophobic force between the cis-azobenzene units and a -(CH 2)n-chain. The results establish that the guest selectivity in host-guest chemistry can be controlled by the enforced change in the cavity shape.

Original languageEnglish
Pages (from-to)1905-1909
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number11
Publication statusPublished - 1990
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General Chemistry


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