Recognition and transport of amphiphilic molecules by a new class of inorganic ditopic receptors. The synthesis of M-^t Bu₄-salphen-3n-cr-n complexes and their use (M = Mn,Fe, n = 6) in the transport of tryptophan and serotonin across

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• 作者：Coucouvanis ; Dimitri ; Rosa ; Dell ; Pike ; Jay
• 刊名：Comptes Rendus Chimie
• 出版年：2003
• 出版时间：March, 2003
• 年：2003
• 卷：6
• 期：3
• 页码：317-327
• 全文大小：436 K

文摘

A new class of ditopic receptor molecules have been synthesized and structurally characterized. The unique structural features of these molecules are: (a) a very lipophilic unit that consists of two 3,5-di-t-butylsalicylideneimine moieties that form a square O₂N₂ coordination site and (b) a relatively hydrophilic benzo-18-crown-6 unit capable of binding to alkali metal ions and hydrogen bonding with ammonium functional groups. These molecules are totally insoluble in water but very soluble in non-polar solvents. By virtue of their hydrophilic end, they are able to invade the water-organic solvent interface and retrieve hydrophilic molecules from water solution that subsequently are extracted into the organic solvent. Procedures are described for the syntheses of the {H₂-^tBu₄-salphen-18-cr-6 and also 15-crown-5 and 12-crown-4 derivatives. With dibenzo-crown ethers 2:1 ^tBu₄-salphen:crown ether molecules have been obtained with 18-crown-6, 24-crown-8 and 30-crown-10 ‘bridges’. A variety of metal ions (Mn³⁺, Fe²⁺, Fe³⁺, Co²⁺, Ni²⁺ and Cu²⁺) have been incorporated within the N₂O₂ cavity of the salphen subunits in the 18-crown-6 and 24-crown-8 hybrids. An account of structural features and transport characteristics for some of these molecules are reported. The results of a detailed study of the transport of tryptophan and serotonin across CHCl₃ bulk liquid membranes are discussed for these processes that follow Michaelis–Menten kinetics. To cite this article: D. Coucouvanis et al., C. R. Chimie 6 (2003).