Modulating Paratropicity Strength in Diareno-Fused Antiaromatics
| Autor: | Conerd K. Frederickson, Lev N. Zakharov, Michael M. Haley |
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| Rok vydání: | 2016 |
| Předmět: |
Models
Molecular Pentalene 010405 organic chemistry Chemistry Molecular Conformation Electrons General Chemistry Electronic structure Fluorene 010402 general chemistry Photochemistry Hydrocarbons Aromatic 01 natural sciences Biochemistry Bond order Catalysis 0104 chemical sciences Organic semiconductor chemistry.chemical_compound Colloid and Surface Chemistry Computational chemistry Molecule Cyclobutadiene Antiaromaticity |
| Zdroj: | Journal of the American Chemical Society. 138:16827-16838 |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | 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 Ered1 for the pentalene and indacene core molecules correlates well with their calculated NICSπZZ 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 organic semiconductors. |
| Databáze: | OpenAIRE |
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