Regiocontrolled Formation of a Novel Dioxadithiapentacene

Abstract

The synthesis, 1,2 crystal structure 2,3 and conductive properties 2 of tetrathiapentacene (1) have been investigated. Synthesis of alkyl-and alkoxy-substituted deriva-10045

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.…”

Nucleophilic and Radical Heptafluoroisopropoxylation with Redox‐Active Reagents

“…The OCF(CF 3 ) 2 ‐substituted arenes ( 4 ai and 15 ) preferably adopt a conformation in which the OCF(CF 3 ) 2 moiety lies in the plane orthogonal to the aromatic ring ( θ =79–85°), analogously to OCF 3 ‐substituted arenes [25] . This unique conformation is in striking contrast to the behavior of nonfluorinated ArOCH(CH 3 ) 2 , [26a] in which the OCH(CH 3 ) 2 group is in plane of the aromatic ring with a dihedral angle ( θ ) of 7.5°. In the cases of OCF(CF 3 ) 2 ‐substituted heterocycles ( 4 t , 4 u , 4 al , and 4 an ), the dihedral angle ( θ ) of C=C‐O‐CF(CF 3 ) 2 bond is between 57–78°.…”

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.…”