An isosteric triaza analogue of a polycyclic aromatic hydrocarbon monkey saddle
Since a few years, the interest in negatively-curved fused polycyclic aromatic hydrocarbons (PAHs) has significantly increased. Recently, the first chiral negatively-curved PAH with the topology of a monkey saddle was introduced. Herein the synthesis of its triaza congener is reported. The influence...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
2020
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| In: |
Chemistry - a European journal
Year: 2020, Volume: 26, Issue: 64, Pages: 14560-14564 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202002826 |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202002826 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202002826 
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| Author Notes: | Tobias Kirschbaum, Frank Rominger, and Michael Mastalerz |
| Summary: | Since a few years, the interest in negatively-curved fused polycyclic aromatic hydrocarbons (PAHs) has significantly increased. Recently, the first chiral negatively-curved PAH with the topology of a monkey saddle was introduced. Herein the synthesis of its triaza congener is reported. The influence of this CH↔N exchange on photophysical and electrochemical properties is studied as well as the isomerization process of the enantiomers. The aza analogue has a significantly higher inversion barrier, which makes it easier to handle at room temperature. All experimental results are underpinned by theoretical DFT calculations. |
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| Item Description: | First published: 15 June 2020 Gesehen am 03.11.2021 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202002826 |