title: Pentaleno[1,2-a:4,5']diacenaphthylenes: Uniquely Stabilized Pentalene Derivatives.
abstract: We demonstrate the preparation of diacenaphthopentalene derivatives via a palladium-catalyzed dimerization of 1-iodo-2-arylethynyl-acenaphthylenes. The resulting 7,14-diarylpentaleno[1,2-a:4,5a']diacenaphthylenes, which contain four linearly fused five-membered rings, are benchtop stable and behave as hole-transporting or ambipolar semiconductors in organic field effect transistors. The X-ray crystal structure shows the important role of the fused naphthalene unit that enforces a formal pentalene subunit at the central five-membered rings and [5]-radialene-like structures at the proximal five-membered rings. Nucleus-independent chemical shift (NICS) calculations show the internal pentalene rings are intermediate in antiaromaticity character between known pentalene and dibenzopentalenes derivatives. The diacenaphthopentalene derivatives give high optical gap materials owing to a forbidden HOMO to LUMO transition, yet have narrow electrochemical gaps and are reduced at small negative potentials giving LUMO energy levels of -3.57 to -3.74 eV.
authors: Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University , Carbondale, Illinois 62901, United States.
authors: Bingxin
authors: B
authors: Yuan
authors: Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University , Carbondale, Illinois 62901, United States.
authors: Junpeng
authors: J
authors: Zhuang
authors: Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University , Carbondale, Illinois 62901, United States.
authors: Kristopher M
authors: KM
authors: Kirmess
authors: Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University , Carbondale, Illinois 62901, United States.
authors: Chelsea N
authors: CN
authors: Bridgmohan
authors: Department of Chemistry, The University of Vermont , Burlington, Vermont 05405, United States.
authors: Adam C
authors: AC
authors: Whalley
authors: Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University , Carbondale, Illinois 62901, United States.
authors: Lichang
authors: L
authors: Wang
authors: Department of Chemistry and Biochemistry and the Materials Technology Center, Southern Illinois University , Carbondale, Illinois 62901, United States.
authors: Kyle N
authors: KN
authors: Plunkett