Details
| Original language | English |
|---|---|
| Pages (from-to) | 6686-6695 |
| Number of pages | 10 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2014 |
| Issue number | 30 |
| Publication status | Published - 1 Sept 2014 |
Abstract
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. New ferrocenes bearing highly extended π systems with nitrile, nitro, and dimethylamino end groups are prepared that include a push-pull-substituted system. The redox properties of the new compounds have been characterized by cyclic voltammetry.
Keywords
- Alkynes, Conjugation, Cross coupling, Pi interactions, Redox chemistry, Sandwich compounds
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, Vol. 2014, No. 30, 01.09.2014, p. 6686-6695.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Ferrocenes bearing highly extended π systems with nitrile, nitro, and dimethylamino end groups
AU - Krauße, Nico
AU - Butenschön, Holger
PY - 2014/9/1
Y1 - 2014/9/1
N2 - 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. New ferrocenes bearing highly extended π systems with nitrile, nitro, and dimethylamino end groups are prepared that include a push-pull-substituted system. The redox properties of the new compounds have been characterized by cyclic voltammetry.
AB - 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. New ferrocenes bearing highly extended π systems with nitrile, nitro, and dimethylamino end groups are prepared that include a push-pull-substituted system. The redox properties of the new compounds have been characterized by cyclic voltammetry.
KW - Alkynes
KW - Conjugation
KW - Cross coupling
KW - Pi interactions
KW - Redox chemistry
KW - Sandwich compounds
UR - http://www.scopus.com/inward/record.url?scp=85028224972&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201402831
DO - 10.1002/ejoc.201402831
M3 - Article
AN - SCOPUS:85028224972
VL - 2014
SP - 6686
EP - 6695
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 30
ER -