Self-assembly of C(60) pi-extended tetrathiafulvalene (exTTF) dyads on gold surfaces.
The first self-assembly of a C60 pi-extended tetrathiafulvalene (exTTF) dyad on a gold surface is reported. Four fullerene derivatives, two of them containing p-quinonoid pi-extended tetrathiafulvalenes (exTTFs), have been synthesized, and their solution electrochemistry has been investigated by means of cyclic voltammetry. Fullerene-containing SAMs of thioctic acid derivatives 3 and 6 have also been investigated by cyclic voltammetry. The cyclic voltammograms of both compounds exhibit three reversible reduction waves, and for compound 6, one irreversible oxidation process corresponding to the oxidation of the exTTF subunit is observed. Stable self-assembled monolayers (SAMs) of fullerene derivative 3 were formed on gold surfaces, whereas dyad 6 does not present a very clear electrochemical response, most probably as a result of structural rearrangements on the monolayer or charge transfer between the C60 and exTTF moieties.
Sierra
María
M
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, E-28040 Madrid, Spain.
Herranz
M Angeles
MA
Zhang
Sheng
S
Sanchez
Luis
L
Martín
Nazario
N
Echegoyen
Luis
L
D004563:Electrochemistry; D037741:Fullerenes / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013499:Surface Properties
D037741:Fullerenes; D006571:Heterocyclic Compounds; D006046:Gold; C063887:tetrathiafulvalene; C069837:fullerene C60