title: Modulating Paratropicity Strength in Diareno-Fused Antiaromatics.
abstract: Understanding and controlling the electronic structure of molecules is crucial when designing and optimizing new organic semiconductor materials. We report the regioselective synthesis of eight π-expanded diarenoindacene analogues based on the indeno[1,2-b]fluorene framework along with the computational investigation of an array of diareno-fused antiaromatic compounds possessing s-indacene, pentalene, or cyclobutadiene cores. Analysis of the experimental and computationally derived optoelectronic properties uncovered a linear correlation between the bond order of the fused arene bond and the paratropicity strength of the antiaromatic unit. The Ered1for the pentalene and indacene core molecules correlates well with their calculated NICSπZZvalues. The findings of this study can be used to predict the properties of, and thus rationally design, new diareno-fused antiaromatic molecules for use as organic semiconductors.
authors.affiliation: Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon , Eugene, Oregon 97403-1253, United States.
authors.forename: Conerd K
authors.initials: CK
authors.lastname: Frederickson
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 & Biochemistry and the Materials Science Institute, University of Oregon , Eugene, Oregon 97403-1253, United States.
authors.forename: Michael M
authors.identifier: 0000-0002-7027-4141
authors.initials: MM
authors.lastname: Haley
mesh_terms: D004583:Electrons; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D006841:Hydrocarbons, Aromatic