Homoconjugation and intramolecular charge transfer in extended aromatic triptycenes with different π-planes
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...
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| Hauptverfasser: | , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
November 4, 2020
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| In: |
The journal of organic chemistry
Year: 2020, Jahrgang: 85, Heft: 23, Pages: 15256-15272 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.0c02100 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.0c02100
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| Verfasserangaben: | Kevin Baumgärtner, Marvin Hoffmann, Frank Rominger, Sven M. Elbert, Andreas Dreuw, and Michael Mastalerz |
| Zusammenfassung: | 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. |
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| Beschreibung: | Gesehen am 13.02.2022 |
| Beschreibung: | Online Resource |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.0c02100 |