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Preparation, Structure, and Anion Sensing Properties of 1,n-Diaza[n]ferrocenophanes
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posted on 2005-08-19, 00:00 authored by Francisco Otón, Alberto Tarraga, Arturo Espinosa, Maria D. Velasco, Delia Bautista, Pedro MolinaThe 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.
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ferrocenespectroscopicfluoride anionsdisplayazaheterocyclecrystal structuremethodredoxdownfield shiftcompound 4typePropertiessynthesisurea protonsbiAniondihydrogenphosphatecouplePreparationframeworkDiazaguanidinecathodic shifttetrazaazaferrocenophaneTetraza10 showferrocenophaneelectrochemicaldiazaferrocenyleneureido moieties