PAHs Containing both Heptagon and Pentagon: Corannulene Extension by [5+2] Annulation
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- 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 theUtilizing 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.…
Autor(en): | Matthias Schnitzlein, Carina Mützel, Kazutaka Shoyama, Jeffrey M. Farrell, Frank WürthnerORCiDGND |
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URN: | urn:nbn:de:bvb:20-opus-262627 |
Dokumentart: | Artikel / Aufsatz in einer Zeitschrift |
Institute der Universität: | Fakultät für Chemie und Pharmazie / Institut für Organische Chemie |
Sprache der Veröffentlichung: | Englisch |
Titel des übergeordneten Werkes / der Zeitschrift (Englisch): | European Journal of Organic Chemistry |
Erscheinungsjahr: | 2022 |
Band / Jahrgang: | 2022 |
Heft / Ausgabe: | 5 |
Aufsatznummer: | e202101273 |
Originalveröffentlichung / Quelle: | European Journal of Organic Chemistry 2022, 2022(5):e202101273. DOI: 10.1002/ejoc.202101273 |
DOI: | https://doi.org/10.1002/ejoc.202101273 |
Allgemeine fachliche Zuordnung (DDC-Klassifikation): | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Freie Schlagwort(e): | Corannulene; annulation; aromaticity; azulene; polycyclic aromatic hydrocarbons |
Datum der Freischaltung: | 07.12.2022 |
Lizenz (Deutsch): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |