Synthesis, Properties, and X-ray Structure of 6-Aza-5,7,12,14-tetrathiapentacene as a Novel Polyheterocyclic Electron Donor, and Related Compounds

Synthesis and structure of bis(ethylenedioxy)‐1,4,5,8‐tetraselenanaphthalene

“…Thus, BEDO‐TSeN shows two irreversible oxidation waves ( E pa 1 = 0.62 and E pa 2 = 0.95 V vs Fc/Fc + ) in the cyclic voltammetric analysis (Figure ), and the estimated HOMO level at −5.42 eV based on the irreversible oxidation potential at 0.62 V is roughly comparable to the calculated HOMO level at −5.06 eV. The oxidation potentials are similar to those of TTN and the cyclopenta‐fused derivative of 3 but seem to be higher than those of 1,4‐dithiins,[16] presumably due to the non‐planar, zig‐zag structure of BEDO‐TSeN as shown in Figure B.…”

Novel Approach to Ladder-Type Polymers: Polydithiathianthrene via the Intramolecular Acid-Induced Cyclization of Methylsulfinyl-Substituted Poly(meta-phenylene sulfide)

“…Furthermore the melting point of 22 a is identical to the reported melting point of tetrathiapentacene, synthesized by other chemical methods. [22,23] However, the yield from the herein described ring closure method towards 22 a is by far the highest ever reported. Scheme 5.…”

“…[22,23,27] ESR-measurements of 4 in trifluoromethanesulfonic acid showed a strong signal, indicating that radical species are formed, whose nature, however, is not yet clear. The UV/vis/NIR spectra of 24, 22 and 4 show two characteristic absorptions: one intense and very sharp transition at low wavelengths and one broad absorption at higher wavelengths.…”

Diquino[3,4-b;4′,3′-e][1,4]dithiine

“…Thia-and azapentacycles are considered to be a new type of electron donor (Boros et al, 1998;Ahmad et al, 1996;Marti et al, 1994;Engman et al, 1988), which show photoelectric properties (Yoshida et al, 1994) and constitute the active layer in a field-effect transistor (FET) device (Miao et al, 2003). The diazadithiapentaphenes (I) and (II) (common names: isothioquinanthrene and thioquinanthrene, respectively) and the diazadithiapentacenes (III) and (IV) have proved to be excellent substrates in the search for new quinoline derivatives via 1,4-dithiine ring-opening reactions (e.g.…”