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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 E_red¹ for the pentalene and indacene core molecules correlates well with their calculated NICS_πZZ values. 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 …