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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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Bibliographic Details
Main Authors: Baumgärtner, Kevin (Author) , Hoffmann, Marvin (Author) , Rominger, Frank (Author) , Elbert, Sven (Author) , Dreuw, Andreas (Author) , Mastalerz, Michael (Author)
Format: Article (Journal)
Language:English
Published: November 4, 2020
In: The journal of organic chemistry
Year: 2020, Volume: 85, Issue: 23, Pages: 15256-15272
ISSN:1520-6904
DOI:10.1021/acs.joc.0c02100
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.0c02100
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Author Notes:Kevin Baumgärtner, Marvin Hoffmann, Frank Rominger, Sven M. Elbert, Andreas Dreuw, and Michael Mastalerz
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Summary: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.
Item Description:Gesehen am 13.02.2022
Physical Description:Online Resource
ISSN:1520-6904
DOI:10.1021/acs.joc.0c02100

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