Efficient Isomer-Pure Synthesis of a Benzo[b]thiophene Analogue of Pentacene^,

Abstract

Isomer-pure thieno[3,2-f:4,5-f ']bis[1]benzothiophene (2, n = 2) has been synthesized in an efficient four step approach without column chromatography.

Vibronic Coupling in Organic Semiconductors: The Case of Fused Polycyclic Benzene–Thiophene Structures

“…[13,14] The gas-phase photoelectron spectra of TBBT and BDT were collected by using the instrument and experimental procedures reported in more detail elsewhere. [22] Both isomers of TBBT sublimed at 190-240 8C and both isomers of BDT sublimed at 55-80 8C.…”

“…Anthony et al have recently demonstrated [6] that, as in the case of pentacene, directed functionalization of the central ring of ADT further increases the solubility and tunes the solid-state ordering in favor of p stacking. More recently, some of us [13,14] reported two thienobisbenzothiophene (TBBT) isomers (see Figure 1), in which, in comparison to ADT, the central benzene ring is also replaced with a thiophene ring. The X-ray analysis [14] of the anti-TBBT isomer reveals a favorable molecular overlap along the crystal c axis, which suggests that TBBT and their derivatives might be promising materials for applications in organic electronics.…”

Metalated heterocycles in organic synthesis: Recent applications

“…32 There are also examples of the use of these heteroaryllithiums in addition reactions to aldehydes for the preparation of core-modified porphyrins, 33 hetero-calix [4]pyrroles, 34 benzo[b]thiophene analogues of pentacene 35 or inhibitors of type II 17β-hydroxysteroid dehydrogenase, 36 as well as in additions to phenanthrolines. 37 2-Alkylation reactions of the corresponding 2-thienyllithiums have been used, for instance, in the synthesis of dialkyloligothiophenes for molecular electronic applications.…”

Metalated Heterocycles in Organic Synthesis: Recent Applications

“…30 Examples of the use of 2-lithiothiophenes for bromination reactions in the synthesis of oligothiophenes, 31 or for double addition to 2-thienylcarboxylated compounds in the preparation of multicharged methinium compounds can be found. 32 There are also examples of the use of these heteroaryllithiums in addition reactions to aldehydes for the preparation of core-modified porphyrins, 33 hetero-calix [4]pyrroles, 34 benzo[b]thiophene analogues of pentacene 35 or inhibitors of type II 17β-hydroxysteroid dehydrogenase, 36 as well as in additions to phenanthrolines. 37 2-Alkylation reactions of the corresponding 2-thienyllithiums have been used, for instance, in the synthesis of dialkyloligothiophenes for molecular electronic applications.…”