Synthesis and Metal Binding Properties of Anthraquinone Bridged with Coumarin

作者:

DOI: 10.5012/BKCS.2007.28.9.1585

关键词: Cation bindingAnthraquinonesChromophoreAnthraquinoneChemistrySemiquinoneCation transportPhotochemistryCrown etherEther

摘要: Molecular switching in macrocyclic polyether systems has been the subject of intense study during past 30 years. Especially, photochemical well-studied by Shinkai, Ueno, Takagi, Tabushi, and others. In addition, changes pH, light oxidation-reduction chemistry have all explored as mechanisms. The lariat ethers, podands having nitroaromatic sidearms similar species derived from anthraquinones concerned with electrochemical switching. Especially anthraquinone system is an interesting one for reducible switchable ethers because its anion stable months water so long oxygen excluded. Although (noncyclic polyethylene glycols) generally exhibit poor cation binding, when combined semiquinone nucleus, very strong complexation observed radical anion. can be used electrochemically switched transport bulk organic membranes both monoanion dianion formed detected. Both oneelectron two-electron reduction lead to enhanced binding anthraquinone-derived ethers. Anthraquinones differ significantly their ability undergo discrete or two electron also substituted surprising geometrical effects process. Gokel co-workers reported armed based on ring systems, which showed enhancement cyclic voltammetry. 1,8-Anthraquinone crown ether a total six donors macrocycling exceptionally binder not only reduced, but neutral form well. Anthraquinone plays important role various colorimetric sensor systems. coumarins are chromophores photophysical properties, convert into fluorescent probes alkali metal ions. Herein we synthesized new receptor 4 coumarin units, studied properties guests. Results Discussion

参考文章(19)
Seiji Shinkai, Toshiyuki Ogawa, Yumiko Kusano, Osamu Manabe, Kiyoshi Kikukawa, Tokio Goto, Tsutomu Matsuda, Photoresponsive crown ethers. 4. Influence of alkali metal cations on photoisomerization and thermal isomerization of azobis(benzocrown ethers) Journal of the American Chemical Society. ,vol. 104, pp. 1960- 1967 ,(1982) , 10.1021/JA00371A027
PÉTER BAKÓ, ATTILA MAKÓ, GYÖRGY KEGLEVICH, DÓRA K. MENYHÁRT, TAMÁS SEFCSIK, JENŐ FEKETE, Alkali Metal- and Ammonium Picrate Extraction and Complex Forming Capabilities of d-Glucose and d-Mannose-based Lariat Ethers Journal of Inclusion Phenomena and Macrocyclic Chemistry. ,vol. 55, pp. 295- 302 ,(2006) , 10.1007/S10847-006-9051-Z
Lokman Torun, Thomas W. Robison, Jan Krzykawski, David W. Purkiss, Richard A. Bartsch, Side arm participation in lariat ether carboxylate-alkali metal cation complexes in solution Tetrahedron. ,vol. 61, pp. 8345- 8350 ,(2005) , 10.1016/J.TET.2005.06.093
Deborah A. Gustowski, Milagros. Delgado, Vincent J. Gatto, Luis. Echegoyen, George W. Gokel, Electrochemical switching in anthraquinone-substituted carbon-pivot lariat ethers and podands: chain length effects in geometric and electronic cooperativity. Journal of the American Chemical Society. ,vol. 108, pp. 7553- 7560 ,(1986) , 10.1021/JA00284A019
Seiji Shinkai, Takahiro Nakaji, Yoshihiro Nishida, Toshiyuki Ogawa, Osamu Manabe, Photoresponsive Crown Ethers. 1. Cis-Trans Isomerism of Azobenzene as a Tool to Enforce Conformational-Changes of Crown Ethers and Polymers Journal of the American Chemical Society. ,vol. 102, pp. 5860- 5865 ,(1980) , 10.1021/JA00538A026
Youhei Inoue, Paul Kuad, Yasushi Okumura, Yoshinori Takashima, Hiroyasu Yamaguchi, Akira Harada, Thermal and photochemical switching of conformation of poly(ethylene glycol)-substituted cyclodextrin with an azobenzene group at the chain end. Journal of the American Chemical Society. ,vol. 129, pp. 6396- 6397 ,(2007) , 10.1021/JA071717Q
Itsuro Tomatsu, Akihito Hashidzume, Akira Harada, Contrast Viscosity Changes upon Photoirradiation for Mixtures of Poly(acrylic acid)-Based α-Cyclodextrin and Azobenzene Polymers Journal of the American Chemical Society. ,vol. 128, pp. 2226- 2227 ,(2006) , 10.1021/JA058345A
Richard A Bissell, Emilio Córdova, Angel E. Kaifer, J. Fraser Stoddart, A chemically and electrochemically switchable molecular shuttle Nature. ,vol. 369, pp. 133- 137 ,(1994) , 10.1038/369133A0
Milagros. Delgado, Deborah A. Gustowski, Hyunsook K. Yoo, Vincent J. Gatto, George W. Gokel, Luis. Echegoyen, Contrasting one- and two-cation binding behavior in syn- and anti-anthraquinone bibracchial podand (BiP) mono- and dianions assessed by cyclic voltammetry and electron paramagnetic resonance spectroscopy Journal of the American Chemical Society. ,vol. 110, pp. 119- 124 ,(1988) , 10.1021/JA00209A019
Md. Aminur Rahmen, Nak-Hyun Kwon, Mi-Sook Won, Myung-Ho Hyun, Yoon-Bo Shim, Selective binding of NH4 + by redox-active crown ethers: application to a NH4 + sensor. Analytical Chemistry. ,vol. 76, pp. 3660- 3665 ,(2004) , 10.1021/AC0353841