title: Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character.
abstract: Indeno[1,2-b]fluorenes (IFs), while containing 4n π-electrons, are best described as two aromatic benzene rings fused to a weakly paratropics-indacene core. In this study, we find that replacement of the outer benzene rings of an IF with benzothiophenes allows the antiaromaticity of the centrals-indacene to strongly reassert itself. Herein we report a combined synthetic, computational, structural, and materials study ofanti-andsyn-indacenodibenzothiophenes (IDBTs). We have developed an efficient and scalable synthesis for preparation of a series of aryl- and ethynyl-substituted IDBTs. NICS-XY scans and ACID calculations reveal an increasingly antiaromatic core from [1,2-b]IF toanti-IDBT, withsyn-IDBT being nearly as antiaromatic as the parents-indacene. As an initial evaluation, the intermolecular electronic couplings and electronic band structure of a diethynylanti-IDBT derivative reveal the potential for hole and / or electron transport. OFETs constructed using this molecule show the highest hole mobilities yet achieved for a fully conjugated IF derivative.
authors.affiliation: Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, United States.
authors.forename: Jonathan L
authors.initials: JL
authors.lastname: Marshall
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan.
authors.forename: Kazuyuki
authors.initials: K
authors.lastname: Uchida
authors.affiliation: Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, United States.
authors.forename: Conerd K
authors.initials: CK
authors.lastname: Frederickson
authors.affiliation: Otto-Diels-Institute of Organic Chemistry, University of Kiel, Otto-Hahn-Platz 4, Kiel 24098, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Schütt
authors.affiliation: Department of Physics, Wake Forest University, Winston-Salem, North Carolina 27109, United States.
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Zeidell
authors.affiliation: Department of Physics, Wake Forest University, Winston-Salem, North Carolina 27109, United States.
authors.forename: Katelyn P
authors.initials: KP
authors.lastname: Goetz
authors.affiliation: Department of Chemistry and Center of Applied Energy Research, University of Kentucky, Lexington, Kentucky 40506, United States.
authors.forename: Tristan W
authors.initials: TW
authors.lastname: Finn
authors.affiliation: Department of Chemistry and Center of Applied Energy Research, University of Kentucky, Lexington, Kentucky 40506, United States.
authors.forename: Karol
authors.initials: K
authors.lastname: Jarolimek
authors.affiliation: CAMCOR, University of Oregon, Eugene, Oregon 97403-1433, United States.
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.affiliation: Department of Chemistry and Center of Applied Energy Research, University of Kentucky, Lexington, Kentucky 40506, United States.
authors.forename: Chad
authors.initials: C
authors.lastname: Risko
authors.affiliation: Otto-Diels-Institute of Organic Chemistry, University of Kiel, Otto-Hahn-Platz 4, Kiel 24098, Germany.
authors.forename: Rainer
authors.initials: R
authors.lastname: Herges
authors.affiliation: Department of Physics, Wake Forest University, Winston-Salem, North Carolina 27109, United States.
authors.forename: Oana D
authors.initials: OD
authors.lastname: Jurchescu
authors.affiliation: Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, United States.
authors.forename: Michael M
authors.initials: MM
authors.lastname: Haley