Novel fused D-A dyad and A-D-A triad incorporating tetrathiafulvalene and p-benzoquinone

Dumur F., Gautier N., Gallego-Planas N., ŞAHİN Y., Levillain E., Mercier N., ...Daha Fazla

JOURNAL OF ORGANIC CHEMISTRY, cilt.69, sa.6, ss.2164-2177, 2004 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 69 Sayı: 6
  • Basım Tarihi: 2004
  • Doi Numarası: 10.1021/jo035689f
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.2164-2177
  • Anadolu Üniversitesi Adresli: Hayır

Özet

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.