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Ferrocenes Bearing Highly Extended π Systems with Nitrile, Nitro, and Dimethylamino End Groups
Author(s) -
Krauße Nico,
Butenschön Holger
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402831
Subject(s) - chemistry , nitrile , nitro , cyclic voltammetry , group (periodic table) , stereochemistry , derivative (finance) , phenylene , polymer chemistry , combinatorial chemistry , electrochemistry , crystallography , organic chemistry , electrode , alkyl , financial economics , economics , polymer
Oligophenylene‐ethynylenes are a popular class of molecular wires for molecular electronics. Replacement of some, not all, of the 1,4‐phenylene units by 1,1′‐ferrocenylene moieties generates less rigid entities with a limited conformational flexibility. Within this concept, the syntheses of some 1,1′‐disubstituted ferrocenes that bear arylethynyl or 4‐(arylethynyl)phenyl substituents is presented. In contrast to related compounds with sulfur end groups that were prepared previously, the versions presented here have nitrile end groups, which, according to reported precedence, may serve as points of attachment to gold surfaces. A crystal structure analysis of an unusual diferrocenylethyne derivative is included. In addition, one representative with a push‐pull disubstitution that has a nitro and a dimethylamino end group is presented. Many of the prepared compounds have been characterized by cyclic voltammetry.