https://scholars.lib.ntu.edu.tw/handle/123456789/612089
標題: | PAHs Containing both Heptagon and Pentagon: Corannulene Extension by [5+2] Annulation | 作者: | Schnitzlein, Matthias Mutzel, Carina Shoyama, Kazutaka Farrell, Jeffrey M. Wurthner, Frank JEFFREY M. FARRELL |
公開日期: | 2022 | 卷: | 2022 | 期: | 5 | 來源出版物: | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 摘要: | Utilizing Pd-catalyzed [5+2] annulation a series of heptagon-extended corannulenes could be synthesized from a borinic acid precursor furnished by C?H borylation strategy. Single-crystal X-ray analysis revealed the presence of two conformational enantiomers crystallizing in a racemic mixture. Through their embedded five- and seven-membered rings these polycyclic aromatic hydrocarbons (PAHs) exhibit both negative and positive curvature and UV/Vis/NIR absorption spectroscopy as well as cyclic voltammetry experiments provided insights into the influence of larger flanking aromatic systems and electron-donating substituents encompassing the heptagonal ring. Through [5+2] annulation of acenaphthylene an azulene-containing PAH with intriguing optoelectronical properties including a very small bandgap and absorption over the whole visible spectrum could be obtained. Theoretical calculations were employed to elucidate the long-wavelength absorption and aromaticity. ? 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH |
URI: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85121426674&doi=10.1002%2fejoc.202101273&partnerID=40&md5=b933ff864b8d76765c843bf24b9b938e https://scholars.lib.ntu.edu.tw/handle/123456789/612089 |
DOI: | 10.1002/ejoc.202101273 |
顯示於: | 化學系 |
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