Development of Ubiquitous Metal-Catalyzed Novel Reactions and TheirApplication to the Synthesis of π-Conjugated Molecules

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We have developed several new synthetic methods that use ubiquitous, inexpensive, and non-toxic metals such as iron, cobalt, copper as the catalyst, and we exploited these methods for the synthesis of π-conjugated materials of interest for materials science. For example, we developed an iron-catalyzed C-H activation reaction for the synthesis of polysubstituted phenanthrenes, naphthalenes, and congeners, compounds of interest as p-type organic semiconductors. A related reactivity of cobalt was exploited for the alkylation of C-H bonds with alkyl chlorides or alkenes, of interest for the late-stage solubilization of π-conjugated materials or for morphology control in liquid crystals. We also exploited inexpensive, commercially available aromatic sulfonyl chlorides as chlorosulfonylation and arylation reagents in the presence of a copper catalyst to synthesize polysubstituted olefins and indene derivatives, some of them showing strong fluorescence in solution and solid state.