Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character
| Autor: | Karol Jarolimek, Christian Schütt, Lev N. Zakharov, Oana D. Jurchescu, Andrew M. Zeidell, Rainer Herges, Michael M. Haley, Jonathan L. Marshall, Tristan W. Finn, Conerd K. Frederickson, Chad Risko, Katelyn P. Goetz, Kazuyuki Uchida |
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| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Aryl Intermolecular force General Chemistry Conjugated system 010402 general chemistry 01 natural sciences Article 0104 chemical sciences 3. Good health chemistry.chemical_compound chemistry Computational chemistry Molecule Benzene Electronic band structure Derivative (chemistry) Antiaromaticity |
| Zdroj: | Chemical Science. 7:5547-5558 |
| ISSN: | 2041-6539 2041-6520 |
| Popis: | Indeno[1,2-b]fluorenes (IFs), while containing 4n π-electrons, are best described as two aromatic benzene rings fused to a weakly paratropic s-indacene core. In this study, we find that replacement of the outer benzene rings of an IF with benzothiophenes allows the antiaromaticity of the central s-indacene to strongly reassert itself. Herein we report a combined synthetic, computational, structural, and materials study of anti- and syn-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 to anti-IDBT, with syn-IDBT being nearly as antiaromatic as the parent s-indacene. As an initial evaluation, the intermolecular electronic couplings and electronic band structure of a diethynyl anti-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. |
| Databáze: | OpenAIRE |
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