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Oligonuclear Amide‐bridged Ferrocenes from N ‐Fmoc Protected 1‐Amino‐1′‐fluorocarbonyl Ferrocene
Author(s) -
Heinze Katja,
Siebler Daniel
Publication year - 2007
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200700157
Subject(s) - ferrocene , intramolecular force , chemistry , hydrogen bond , amide , intermolecular force , carboxylic acid , polymer chemistry , medicinal chemistry , electrochemistry , stereochemistry , molecule , organic chemistry , electrode
Oligoamides with ferrocenes in the backbone were prepared by stepwise coupling techniques using ferrocenoyl fluorides. The key building block is N ‐Fmoc protected 1‐amino‐1′‐fluorocarbonyl ferrocene FmocNH–fn–COF ( 5 ). Stepwise coupling of 5 with amino ferrocene Fc–NH 2 and (after deprotection) ferrocene carboxylic acid fluoride Fc–COF or 1‐(acetylamino)‐ferrocene‐1′‐carboxylic acid fluoride CH 3 C(O)NH–fc–COF yielded the dinuclear ferrocene Fc–NHC(O)–fn–NHFmoc ( 6 ) and the trinuclear ferrocenes Fc–NHC(O)–fn–NHC(O)–Fc ( 8 ) and Fc–NHC(O)–fn–NHC(O)–fn–NHC(O)CH 3 ( 11 ), respectively. In solution 6 prefers a conformation with an intramolecular hydrogen bond while in the solid state intermolecular hydrogen bonds prevail. The electronic interaction of the ferrocene units in bi‐ and trinuclear ferrocenes with amide linkers has been assessed by electrochemical studies.