TY - JOUR
T1 - A photochemically activated cyclophane
AU - Shinkai, Seiji
AU - Yoshioka, Akiko
AU - Nakayama, Hatsumi
AU - Manabe, Osamu
PY - 1990/12/1
Y1 - 1990/12/1
N2 - 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.
AB - 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.
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U2 - 10.1039/P29900001905
DO - 10.1039/P29900001905
M3 - Article
AN - SCOPUS:37049078447
SP - 1905
EP - 1909
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
SN - 1470-1820
IS - 11
ER -