Photoresponsive crown ethers. 12. Photocontrol of metal ion complexation with thiacrown ethers.
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概要
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Thiacrown ethers with a photofunctional azolinkage were synthesized to control their binding ability by an on-off light switch: They are the N<SUB>2</SUB>S<SUB>4</SUB> crowns capped with 2,2′-azopyridine (<B>1</B>) or azobenzene (<B>2</B>). The cis-trans isomerism occurred reversibly by photoirradiation. The binding ability, evaluated by solvent extraction, showed that (i) the order of the affinity for Hg<SUP>2+</SUP> is <I>N</I>,<I>N</I>′-dibenzoylated N<SUB>2</SUB>S<SUB>4</SUB> crown (<B>4</B>)≈photoirradiated <B>1</B>><I>trans</I>-<B>1</B>>photoirradiated <B>2</B>><I>trans</I>-<B>2</B>, (ii) neither <I>trans</I>-<B>2</B> nor <B>4</B> shows significant affinity toward heavy metal ions such as Cu<SUP>2+</SUP>, Co<SUP>2+</SUP>, Ni<SUP>2+</SUP>, and Pb<SUP>2+</SUP>, (iii) <I>trans</I>-<B>1</B> has a slight affinity (Ex% 5.9%) for Cu<SUP>2+</SUP>,whereas photoisomerized <B>1</B> shows the remarkably enhanced affinity (Ex% 93.9%) with Cu<SUP>2+</SUP>, and (iv) such light-induced improvement is not seen for <B>2</B>. The relatively poor binding ability of <B>2</B> and <B>4</B> is rationalized in terms of the unfavorable inside-out conformation of the N<SUB>2</SUB>S<SUB>4</SUB> crown ring. The remarkable affinity change in <I>cis</I>-<B>1</B> is probably due to the cooperative contribution of the thiacrown and the azopyridine cap constructing a new ligand site. <B>1</B> was used as a carrier for Cu<SUP>2+</SUP> transport through a liquid membrane. It was found that the rate is efficiently accelerated by UV-light irradiation.
- 公益社団法人 日本化学会の論文
著者
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Shinkai Seiji
Department Of Applied Chemistry Faculty Of Engineering Kyushu University
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Honda Yoshihiro
Department Of Cardiovascular Surgery Yamanashi Central Hospital
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MANABE Osamu
Department of Applied Chemistry, Faculty of Engineering, Nagasaki University
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Ueda Kaori
Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University
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