Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character. Issue 8 (27th May 2016)

• Record Type: Journal Article
• Authors: Marshall, Jonathan L.; Uchida, Kazuyuki; Frederickson, Conerd K.; Schütt, Christian; Zeidell, Andrew M.; Goetz, Katelyn P.; Finn, Tristan W.; Jarolimek, Karol; Zakharov, Lev N.; Risko, Chad; Herges, Rainer; Jurchescu, Oana D.; Haley, Michael M.
• Is Part Of: Chemical science. Volume 7:Issue 8(2016:Aug.)
• Page Start: 5547
• Page End: 5558
• Publication Date: 2016-05-27
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6sc00950f
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Exchanging fused benzenes for benzothiophenes results in pronounced antiaromaticity in the indacene core. Abstract : 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.