Intramolecular electronic interactions in conjugated ferrocene-π-extended-tetrathiafulvalene donor-π-donor molecular hybrids

被引:67
作者
Liu, SG
Pérez, I
Martín, N [1 ]
Echegoyen, L
机构
[1] Univ Complutense Madrid, Fac Ciencias Quim, Dept Quim Organ, E-28040 Madrid, Spain
[2] Univ Miami, Dept Chem, Coral Gables, FL 33124 USA
关键词
D O I
10.1021/jo001149w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of new hybrid ferrocene and pi -extended tetrathiafulvalene (TTF) donor(1)-pi -donor(2) molecular assemblies 16a-c has been carried out by a Wittig-Horner reaction of the respective phosphonate esters 15a-c with 2-(2-ferrocenylvinyl)-9,10-anthraquinone (18) prepared by olefination of ferrocenecarboxaldehyde (14) and the anthraquinone phosphonium salt 17. Electrochemical studies show that the D-1-pi -D-2 (D = donor) molecular assemblies 16a-c essentially retain the redox characteristics of both ferrocene and the pi -extended TTF components and the effects of solvent, temperature, scan rate, and working electrode are significant. Most importantly, pronounced intramolecular electronic interactions between the two donor moieties were observed by cyclic voltammetry and Osteryoung square wave voltammetry in both the ground and charged states. Semiempirical calculations support the electrochemical observations.
引用
收藏
页码:9092 / 9102
页数:11
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