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1,n-二氮杂[n]二茂铁并苯的制备、结构及阴离子传感特性

Preparation, structure, and anion sensing properties of 1,n-diaza[n]ferrocenophanes.

作者信息

Otón Francisco, Tarraga Alberto, Espinosa Arturo, Velasco Maria D, Bautista Delia, Molina Pedro

机构信息

Departamento de Quimica Organica, Facultad de Quimica, Universidad de Murcia, Campus de Espinardo, E-30100 Murcia, Spain.

出版信息

J Org Chem. 2005 Aug 19;70(17):6603-8. doi: 10.1021/jo050458p.

DOI:10.1021/jo050458p
PMID:16095276
Abstract

The synthesis of structurally new types of azaferrocenophanes is reported in this note: 4, which comprises a 1,2-fused azaheterocycle to a 1,3-diaza[3]ferrocenophane framework; 1,3-diaza[3]ferrocenophanes 5 and 7, which can be considered as a 1,1'-ferrocenylene N,N'-guanidine or urea, respectively; and 1,3,6,8-tetraza[8]ferrocenophanes 9 and 10, bearing two ureido moieties in the ansa-bridge. These compounds were prepared directly from 1,1'-bis(isocyanato)ferrocene 1 and thoroughly characterized by spectroscopic means. Tetraza[8]ferrocenophanes 9 and 10 show spectral and electrochemical anion-sensing action: they display a selective downfield shift of the urea protons and a cathodic shift of the ferrocene/ferrocinium redox couple with dihydrogenphosphate and fluoride anions. The crystal structure of compound 4 has been determined by single-crystal X-ray methods.

摘要

本笔记报道了新型结构氮杂二茂铁环蕃的合成

4,它由一个与1,3-二氮杂[3]二茂铁环蕃骨架稠合的1,2-氮杂环组成;1,3-二氮杂[3]二茂铁环蕃5和7,它们可分别视为1,1'-二茂铁撑N,N'-胍或脲;以及1,3,6,8-四氮杂[8]二茂铁环蕃9和10,在桥链中带有两个脲基部分。这些化合物直接由1,1'-双(异氰酸酯基)二茂铁1制备,并通过光谱手段进行了全面表征。四氮杂[8]二茂铁环蕃9和10表现出光谱和电化学阴离子传感作用:它们在磷酸二氢根和氟离子存在下,脲基质子出现选择性的向低场位移,二茂铁/二茂铁鎓氧化还原对出现阴极位移。化合物4的晶体结构已通过单晶X射线方法测定。

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