Dimers of Anthrathiophene and Anthradithiophene Derivatives: Synthesis and Characterization

Abstract

Synthesis, isolation, and characterization of derivatives of an anthrathiophene dimer (TOTBAT) and of anthradithiophene oligomers (ADTO), possessing octylthiophene units on their backbone, are described. These semiconductors are prepared through oxidative copper(II) chloride coupling. The spectroscopic properties and stability of these newly synthesized semiconductors were evaluated and supported by quantum-chemical calculations.

Anthradithiophene Derivatives Substituted at the 2,8‐Positions by Formyl and Triphenylamine Units: Synthesis, Optical, and Electrochemical Properties

“…FADT and TPAADT were prepared as presented in Scheme . FADT (purple solid) was obtained in 72 % yield by metalation of ADT 1 6b using n BuLi, followed by reaction of the corresponding dilithiated species with DMF. Note that FADT is produced as a mixture of isomers, as its preparation was made starting from a mixture of syn / anti isomers of ADT 1 .…”

“…5,11‐Bis(5‐octylthiophen‐2‐yl)anthradithiophene (1, syn / anti isomers): Identical procedure described in literature 6b…”

“…Additionally, it has been demonstrated that the presence of such substituents enhances the stability of these derivatives towards photo‐oxidation, especially in solution 5a,5c,6a,8. With this synthetic strategy, chemical reactions involving these compounds were also rendered feasible and were engaged in oligomerization and/or polymerization reactions 6b,9. The synthetic work reported in the literature to increase the stability of this class of semiconductors mainly focuses on the functionalization of the center of their aromatic cores (5,11‐positions of pentacene and ADT cores for instance).…”

Anticipating Acene-Based Chromophore Spectra with Molecular Orbital Arguments

“…). The design principle correctly applies to acene dimers, oligomers and polymers such as A, 37 B, 33 F, 38 G 39 and H, 40 complex geometries such as C,34 I, 41,42 J 43 and K, 44 and to heteroatom-substituted dimers D,35 E,36 and L. 45 R denotes a solubilising or stabilising group. liquid crystals, 41 polymer synthesis, 42 sensors, 45 photovoltaic applications,37,39,43 and one to explore structure-spectrum relationships 32.…”

A Concise and Efficient Route to Electron‐Accepting 2,2′‐[2,2′‐Arenediylbis(11‐oxoanthra[1,2‐b]thiophene‐6‐ylidene)]dipropanedinitriles

“…[4a], , However, for the assembly of bulkier conjugated structures based on two or more AT or ADT fragments, it is necessary to use new approaches that have been little studied. For example, Balandier and co‐workers proposed the CuCl 2 ‐mediated oxidative coupling of lithiated AT derivatives into the corresponding dimers . Unfortunately, this route was not suitable for connecting two AT units with aromatic linkers.…”