Synthesis of Organic Optoelectronic Materials Using Direct C-H Functionalization

Small molecules and polymers with conjugated structures can be used as organic optoelectronic materials. These molecules have conventionally been synthesized by cross-coupling reactions; however, in recent years, direct functionalization of C-H bonds has been used to synthesize organic optoelectronic materials. Representative reactions include direct arylation reactions (C-H/C-X couplings, with X being halogen or pseudo-halogen) and cross-dehydrogenative coupling (C-H/C-H cross-coupling) reactions. Although these reactions are convenient for short-step synthesis, they require regioselectivity in the C-H bonds and suppression of undesired homo-coupling side reactions. This review introduces examples of the synthesis of organic optoelectronic materials using two types of direct C-H functionalization reactions. In addition, we summarize our recent activities in the development of direct C-H functionalization reactions using fluorobenzenes as substrates. This review covers the reaction mechanism and material properties of the resulting products. Conjugated molecules are expected to become the main materials used in organic optoelectronic devices. In the synthesis of organic optoelectronic materials, direct C-H bond functionalization is an efficient method that facilitates a short-step synthesis. This review introduces the synthesis of various materials via direct arylation and cross-dehydrogenative coupling reactions. In addition, the reaction mechanisms and material properties of the products are summarized.image