The effect of central and planar chirality on the electrochemical and chiral sensing properties of ferrocenyl urea H-bonding receptors
作者： Andrea Mulas , Yasmine Willener , James Carr-Smith , Kevin M. Joly , Louise Male
DOI: 10.1039/C5DT00554J
关键词: Stereochemistry 、 Enantiomer 、 Ferrocene 、 Crystallography 、 Hydrogen bond 、 Chemistry 、 Urea 、 Electrochemistry 、 Planar chirality 、 Chirality (chemistry) 、 Carboxylate
摘要: A new series of chiral ureas containing one or two redox-active ferrocene units was synthesised and studied in order to investigate the effect planar chirality central on electrochemical sensing. Binding carboxylate anions organic solvents through H-bond formation caused a negative shift potentials ferrocene/ferrocenium (Fc/Fc+) couples receptors, demonstrating their use as sensors solution. While presence gave no marked improvement sensing capabilities these systems, introduction chirality, addition switched enantiomeric binding preference system also an interesting change appearance some voltammograms, with unusual two-wave behaviour observed upon protected prolinate guest.
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sci-hub.se 参考文章(43)
Hidekazu Miyaji, Simon R. Collinson, Ivan Prokeš, James H. R. Tucker, A ditopic ferrocene receptor for anions and cations that functions as a chromogenic molecular switch Chem. Commun.. pp. 64- 65 ,(2003) , 10.1039/B210227G
Steven R. Miller, Deborah A. Gustowski, Zhi Hong. Chen, George W. Gokel, Luis. Echegoyen, Angel E. Kaifer, Rationalization of the unusual electrochemical behavior observed in lariat ethers and other reducible macrocyclic systems Analytical Chemistry. ,vol. 60, pp. 2021- 2024 ,(1988) , 10.1021/AC00170A007
M. Emília, N.P.R.A. Silva, Armando J.L. Pombeiro, João J.R.Fraústo da Silva, Rudolf Herrmann, Norbert Deus, Tânia J. Castilho, M.Fátima C.G. Silva, Redox potential and substituent effects at ferrocene derivatives. Estimates of Hammett σp and taft polar σ substituent constants Journal of Organometallic Chemistry. ,vol. 421, pp. 75- 90 ,(1991) , 10.1016/0022-328X(91)86433-Q
Yasmine Willener, Kévin M. Joly, Christopher J. Moody, James H. R. Tucker, An exploration of ferrocenyl ureas as enantioselective electrochemical sensors for chiral carboxylate anions. Journal of Organic Chemistry. ,vol. 73, pp. 1225- 1233 ,(2008) , 10.1021/JO701809B
Thomas J. Colacot, A Concise Update on the Applications of Chiral Ferrocenyl Phosphines in Homogeneous Catalysis Leading to Organic Synthesis Chemical Reviews. ,vol. 103, pp. 3101- 3118 ,(2003) , 10.1021/CR000427O
Paul D. Beer, David K. Smith, Tunable bis(ferrocenyl) receptors for the solution-phase electrochemical sensing of transition-metal cations Journal of The Chemical Society-dalton Transactions. pp. 417- 424 ,(1998) , 10.1039/A707278C
Aiichiro Ori, Seiji Shinkai, Electrochemical detection of saccharides by the redox cycle of a chiral ferrocenylboronic acid derivative: a novel method for sugar sensing Journal of The Chemical Society, Chemical Communications. pp. 1771- 1772 ,(1995) , 10.1039/C39950001771
Sun Huikai, Wang Qingmin, Huang Runqiu, Li Heng, Li Yonghong, Synthesis and biological activity of novel cyanoacrylates containing ferrocenyl moiety Journal of Organometallic Chemistry. ,vol. 655, pp. 182- 185 ,(2002) , 10.1016/S0022-328X(02)01553-X
Steve P. Rannard, Nicola J. Davis, Ian Herbert, Synthesis of water soluble hyperbranched polyurethanes using selective activation of AB2 monomers Macromolecules. ,vol. 37, pp. 9418- 9430 ,(2004) , 10.1021/MA0489218
Allen J Bard, Larry R Faulkner, Henry S White, Electrochemical Methods: Fundamentals and Applications ,(1980)