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Beilstein J. Org. Chem. 2015, 11, 930–948, doi:10.3762/bjoc.11.104
Graphical Abstract
Figure 1: TTF dimers with linearly or cross-conjugated bridging units, acyclic or cyclic bridging units.
Scheme 1: Synthesis of TTF dimers with alkyne bridges. TMEDA = N,N,N’,N’-tetramethylethylenediamine. MS = mol...
Scheme 2: Synthesis of TTF dimers with TEE and diethynylpyridine bridges.
Scheme 3: Synthesis of TTF dimer with radiaannulene core.
Figure 2: Molecular structure of 8 (top) and packing diagram (bottom). Crystals were grown from CH2Cl2/MeOH. ...
Figure 3: Bond angles for the cyclic core of 8 (X-ray crystal structure data).
Figure 4: Cyclic voltammograms obtained for the oxidation of compounds 1a ([10]), 2a ([10]), and 3b–8 (this work, ca....
Figure 5: Selected bis-TTFs from literature [20-23].
Figure 6: Cyclic voltammograms obtained for the reduction of compounds 1a, 2a, 6, and 8 in CH2Cl2 (0.1 M Bu4N...
Figure 7: One possible resonance form of the radical anion of 8 with a 14 πz aromatic core.
Scheme 4: Spin–spin interactions resulting from oxidation of TTFdimers.
Figure 8: In situ EPR−UV–vis–NIR cyclic voltammetry of 2b (1 mM) (a) potential dependence of difference vis–N...
Figure 9: In situ EPR−UV–vis–NIR cyclic voltammetry of 4 (0.4 mM): (a) potential dependence of difference vis...
Figure 10: Vis–NIR spectral changes observed during anodic oxidation of each TTF unit to cation radical within...
Figure 11: UV–vis–NIR absorptions of 1b (2.4 mM), 4 (3.5 mM), 5 (2.9 mM), and 8 (1.9 mM) in CH2Cl2 + 0.1 M Bu4...
Figure 12: In situ EPR−UV–vis–NIR cyclic voltammetry of 2b (1 mM) in the cathodic region: (a) potential depend...