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首页> 外文期刊>Chemistry: A European journal >Ferrocene-containing carbohydrate dendrimers [Review]
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Ferrocene-containing carbohydrate dendrimers [Review]

机译：含二茂铁的碳水化合物树枝状聚合物[综述]

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摘要

Aliphatic amines, incorporating one or three (branched) acylated beta-glucopyranosyl residues, were coupled with the acid chloride of ferrocenecarboxylic acid and with the diacid chloride of 1,1'-ferrocenedicarboxylic acid to afford four dendrimer-type, carbohydrate-coated ferrocene derivatives in good yields (54-92%). Deprotection of the peracylated beta-D-glucopyranosyl residues was achieved quantitatively by using Zemplen conditions, affording four water-soluble ferrocene derivatives. When only one of the two cyclopentadienyl rings of the ferrocene unit is substituted, strong complexes are formed with beta-cyclodextrin in H2O, as demonstrated by liquid secondary ion mass spectrometry (LSIMS), H-1 NMR spectroscopy, electrochemical measurements, and circular dichroism spectroscopy. Molecular dynamics calculations showed that the unsubstituted cyclopentadienyl ring is inserted through the cavity of the toroidal host in these complexes. The electrochemical behavior of the protected and deprotected ferrocene-containing dendrimers was investigated in acetonitrile and water, respectively. The diffusion coefficient decreases with increasing molecular weight of the compound. The potential for oxidation of the ferrocene core, the rate constant of heterogeneous electron transfer, and the rate constant for the energy-transfer reaction with the luminescent excited state of the [Ru(bpy)(3)](2+) complex (bpy = 2,2'-bipyridine) are strongly affected by the number (one or two) of substituents and by the number (one or three) of carbohydrate branches present in the substituents. These effects are assigned to shielding of the ferrocene core by the dendritic branches. Electrochemical evidence for the existence of different conformers for one of the dendrimers in aqueous solution was obtained. [References: 135]
机译：脂族胺结合一个或三个（支链）酰化的β-吡喃葡萄糖基残基，与二茂铁羧酸的酰氯和1,1'-二茂铁二羧酸的二酰氯偶合，得到四种树枝状聚合物型，碳水化合物包覆的二茂铁衍生物收率良好（54-92％）。通过使用Zemplen条件，定量实现过酰化的β-D-吡喃葡萄糖基残基的脱保护，得到四种水溶性二茂铁衍生物。当二茂铁单元的两个环戊二烯基环中只有一个被取代时，β-环糊精会在H2O中形成强络合物，如液体二次离子质谱（LSIMS），H-1 NMR光谱，电化学测量和圆二色性所示光谱学。分子动力学计算表明，未取代的环戊二烯基环通过这些配合物中的环状主体的腔插入。分别在乙腈和水中研究了受保护和脱保护的二茂铁树枝状聚合物的电化学行为。扩散系数随着化合物分子量的增加而降低。 [Ru（bpy）（3）]（2+）配合物（bpy）的发光激发态下二茂铁核的氧化电势，异质电子转移的速率常数以及能量转移反应的速率常数＝ 2，2′-联吡啶）受取代基的数目（一个或两个）和存在于取代基中的碳水化合物支链的数目（一个或三个）的强烈影响。这些作用归因于树状分支对二茂铁芯的屏蔽。获得了在水溶液中存在一种树枝状聚合物的不同构象异构体的电化学证据。 [参考：135]

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