TY - JOUR
T1 - PHOTORESPONSIVE CROWN ETHERS - 9. CYLINDRICAL AND PHANE CROWN ETHERS WITH AZOBENZENE SEGMENTS AS A LIGHT-SWITCH FUNCTIONAL GROUP.
AU - Shinkai, Seiji
AU - Minami, Takahide
AU - Ueda, Kaori
AU - Manabe, Osamu
AU - Tashiro, Masashi
AU - Honda, Yoshihiro
PY - 1983
Y1 - 1983
N2 - Cylindrical and phane crown ethers with azobenzene segments as a light-switch functional group were synthesized. Cylindrical ionophores in which two diazacrown ethers are linked by two photoresponsive azobenzene pillars change their binding ability for polymethylenediammonium salts in response to photoirradiation. Thus, the distance between the two crown rings can be photocontrolled. A phane-type ionophore in which 1,23-bis(p-aminophenoxy)-3,6,9,12,15,18,21-heptaoxatricosane is linked by a trans-4,4 prime -azobenzenedicarbonyl segment exhibits no affinity with all alkali metal cations but significantly binds Rb** plus and Cs** plus under UV-light irradiation. This is the example of the 'all-or-nothing' control of the ion-binding ability and implies that a crown-like loop emerges only when the azobenzene segment is photoisomerized to the cis-configuration. These ionophores are categorized to novel photoresponsive crown ethers.
AB - Cylindrical and phane crown ethers with azobenzene segments as a light-switch functional group were synthesized. Cylindrical ionophores in which two diazacrown ethers are linked by two photoresponsive azobenzene pillars change their binding ability for polymethylenediammonium salts in response to photoirradiation. Thus, the distance between the two crown rings can be photocontrolled. A phane-type ionophore in which 1,23-bis(p-aminophenoxy)-3,6,9,12,15,18,21-heptaoxatricosane is linked by a trans-4,4 prime -azobenzenedicarbonyl segment exhibits no affinity with all alkali metal cations but significantly binds Rb** plus and Cs** plus under UV-light irradiation. This is the example of the 'all-or-nothing' control of the ion-binding ability and implies that a crown-like loop emerges only when the azobenzene segment is photoisomerized to the cis-configuration. These ionophores are categorized to novel photoresponsive crown ethers.
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U2 - 10.1246/bcsj.56.1700
DO - 10.1246/bcsj.56.1700
M3 - Article
AN - SCOPUS:0020763583
SN - 0009-2673
VL - 56
SP - 1700
EP - 1704
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 6
ER -