Novel fused donor-acceptor dyad (TTF-Q or D-A) and acceptor-donor-acceptor triad (Q-TTF-Q or A-D-A) incorporating the donor tetrathiafulvalene (TTF) and the acceptor p-benzoquinone (Q) have been synthesized. The solution UV-vis spectra of these molecules display a low-energy absorption band that is attributed to an intramolecular charge transfer between both antagonistic units. The presence of reversible oxidation and reduction waves for the donor and acceptor moieties was shown by cyclic voltammetry, in agreement with the ratio TTF/quinone(s) units. The successive generation from these compounds of the cation radical and anion radical obtained upon (electro)- chemical oxidation and reduction, respectively, was monitored by optical and ESR spectroscopies. The anion radical Q-TTF-Q-¥ triad was demonstrated to be a class II mixed-valence system with the existence of a temperature-dependent intramolecular electron transfer. The crystallographic tendency of these fused systems to overlap in mixed stacks of alternating A-D-A units is also discussed.
Novel Fused D-A Dyad and A-D-A Triad Incorporating Tetrathiafulvalene and p-Benzoquinone / Dumur, F.; Gautier, N.; GALLEGO PLANAS, N.; Sahin, Y.; Levillain, E.; Mercier, N.; Hudhomme, P.; Masino, Matteo; Girlando, Alberto; Lloveras, V.; VIDAL GANCEDO, J.; Veciana, J.; Rovira, C.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 69:(2004), pp. 2164-2177. [10.1021/jo035689f]
Novel Fused D-A Dyad and A-D-A Triad Incorporating Tetrathiafulvalene and p-Benzoquinone
MASINO, Matteo;GIRLANDO, Alberto;
2004-01-01
Abstract
Novel fused donor-acceptor dyad (TTF-Q or D-A) and acceptor-donor-acceptor triad (Q-TTF-Q or A-D-A) incorporating the donor tetrathiafulvalene (TTF) and the acceptor p-benzoquinone (Q) have been synthesized. The solution UV-vis spectra of these molecules display a low-energy absorption band that is attributed to an intramolecular charge transfer between both antagonistic units. The presence of reversible oxidation and reduction waves for the donor and acceptor moieties was shown by cyclic voltammetry, in agreement with the ratio TTF/quinone(s) units. The successive generation from these compounds of the cation radical and anion radical obtained upon (electro)- chemical oxidation and reduction, respectively, was monitored by optical and ESR spectroscopies. The anion radical Q-TTF-Q-¥ triad was demonstrated to be a class II mixed-valence system with the existence of a temperature-dependent intramolecular electron transfer. The crystallographic tendency of these fused systems to overlap in mixed stacks of alternating A-D-A units is also discussed.File | Dimensione | Formato | |
---|---|---|---|
04-JOC-ada.pdf
non disponibili
Tipologia:
Documento in Post-print
Licenza:
Creative commons
Dimensione
460.55 kB
Formato
Adobe PDF
|
460.55 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.