Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/4901
Title: alpha,omega-diferrocenyl cumulene molecular wires. Synthesis, spectroscopy, structure, and electrochemistry
Authors: Skibar, W.
Kopacka, H.
Wurst, K.
Salzmann, C.
Ongania, K. H.
Fabrizi De Biani, Fabrizia 
Zanello, Piero
Bildstein, B.
Issue Date: 2004
Project: None 
Journal: ORGANOMETALLICS
Abstract: 
Cumulene sp-carbon molecular wires C2 [Fc(Ph)CC(Ph)Fc] up to C7 [Fc(Ph)CCCCCCC(Ph)Fc] endcapped by two electroactive ferrocenyl groups are presented in this report. Synthetically, ferrocenyl cumulenes can be built-up by a modular strategy using C1 synthon ferrocenyl(phenyl)ketone as starting material with various acetylenic/propargylic/homopropargylic C2−C5 reagents, taking into account and exploiting the efficient stabilization of an electron-deficient carbenium center by an adjacent ferrocenyl moiety. With increasing cumulene chain length the reactivity of cumulenes increases considerably, indicating steric protection as the main requirement for bulk stability. Even cumulenes C2, C4, and C6 are conjugated “molecular wires” effecting electronic communication between the terminal ferrocenyl substituents, whereas odd cumulenes C3, C5, and C7 are nonconjugated and electronically decoupled due to their orthogonal terminal π-systems. Electrochemically, separate redox waves can be detected up to a C6 cumulene spacer, but the electronic communication between the endcapping redox-active ferrocenyl substituents decreases with increasing cumulene length.
Description: 
40229
URI: http://hdl.handle.net/20.500.12779/4901
ISSN: 0276-7333
DOI: 10.1021/om034233l
Appears in Collections:Publications

Show full item record

Page view(s)

14
Last Week
0
Last month
8
checked on May 6, 2021

Google ScholarTM

Check

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.