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Homoconjugation and Intramolecular Charge Transfer in Extended Aromatic Triptycenes with Different π-Planes

Homoconjugation and Intramolecular Charge Transfer in Extended Aromatic Triptycenes with Different π-Planes

Authors :
Marvin Hoffmann
Sven M. Elbert
Andreas Dreuw
Frank Rominger
Kevin Baumgärtner
Michael Mastalerz
Source :
The Journal of Organic Chemistry. 85:15256-15272
Publication Year :
2020
Publisher :
American Chemical Society (ACS), 2020.

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.

Details

ISSN :
15206904 and 00223263
Volume :
85
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....0f61be00318ab922544c67cba1142137
Full Text :
https://doi.org/10.1021/acs.joc.0c02100