COUPLED HETEROARYL COMPOUNDS VIA REARRANGEMENT OF HALOGENATED HETEROAROMATICS FOLLOWED BY OXIDATIVE COUPLING (ACYL MOIETIES)

摘要

The inventions disclosed and described herein relate to new and efficient generic methods for making a wide variety of compounds having HAr - Z - Har tricyclic cores, wherein HAr is an optionally substituted five or six membered heteroaryl ring, and Hal is a halogen, and Z is a bridging radical, such as S, Se, NR⁵, C(O), C(O)C(O), Si(R⁵)₂, SO, SO₂, PR⁵, BR⁵, C(R⁵)₂ or P(O)R⁵ and both HAr are covalently bound to one another. The synthetic methods employ a "Base-Catalyzed Halogen Dance" reaction to prepare a metallated compound comprising a five or six membered heteroaryl ring comprising a halogen atom, and then oxidatively coupling the reactive intermediate compound. The compounds of Formula (II) and/or oligomer or polymers comprising repeat units having Formula (II) can be useful for making semi-conducting materials, and/or electronic devices comprising those materials. Acyl compounds can be prepared. Heteroarylene substituents can be used. The tricyclic core can be coupled to itself. The Z group also can be strong electron-withdrawing groups such as C=C(CN)₂ or [C=C(CN)₂]₂. Organic electronic devices can be made including field-effect transistors.