Homoconjugation and intramolecular charge transfer in extended aromatic triptycenes with different π-planes

• Verfasst von: Baumgärtner, Kevin [VerfasserIn]
• Verfasst von: Hoffmann, Marvin [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Elbert, Sven [VerfasserIn]
• Verfasst von: Dreuw, Andreas [VerfasserIn]
• Verfasst von: Mastalerz, Michael [VerfasserIn]
• Titel: Homoconjugation and intramolecular charge transfer in extended aromatic triptycenes with different π-planes
• Verf.angabe: Kevin Baumgärtner, Marvin Hoffmann, Frank Rominger, Sven M. Elbert, Andreas Dreuw, and Michael Mastalerz
• E-Jahr: 2020
• Jahr: November 4, 2020
• Umfang: 17 S.
• Fussnoten: Gesehen am 13.02.2022
• Titel Quelle: Enthalten in: The journal of organic chemistry
• Ort Quelle: [S.l.] : American Chemical Society, 1936
• Jahr Quelle: 2020
• Band/Heft Quelle: 85(2020), 23, Seite 15256-15272
• ISSN Quelle: 1520-6904
• DOI: doi:10.1021/acs.joc.0c02100
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1789487307

Abstract

Homoconjugation and intramolecular “through-space” charge transfers are molecular phenomena that have been studied since the 1960s. A detailed understanding and control of these effects would provide a tool to tune the optoelectronic properties of organic molecules in respect of the necessities for applications such as for organic electronics. Triptycene is a perfect candidate to investigate homoconjugation effects due to its three-dimensional alignment of three aromatic phenylene units, separated by two methine bridges. Here, a series of 16 π-extended triptycenes with up to three different permuted electron-accepting units and an electron-rich veratrole unit are studied in detail by UV/vis spectroscopy and cyclovoltammetry in combination with DFT calculations to get a deeper understanding of homoconjugation and charge-transfer processes of triptycenes. Furthermore, the gained knowledge can be exploited to construct triptycene-based electron acceptors with fine-tuned adjustment of electronic properties, such as electron affinities, by thorough choice of the aromatic blades that interact through homoconjugation.