Octacyano-substituted tridecacyclene: a non-benzenoid cyanocarbon with low-lying LUMO and multistage redox properties
Octacyanated tridecacyclene was synthesized from novel brominated tridecacyclene. In the crystal, the saddle-shaped scaffold exhibits a zigzag packing motif governed by an interplay between the inherent geometry of the central cyclooctatetraene moiety and the hydrogen bonding mediated by the dipolar...
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| Main Authors: | , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
10 Mar 2025
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| In: |
Chemical communications
Year: 2025, Volume: 61, Issue: 31, Pages: 5754-5757 |
| ISSN: | 1364-548X |
| DOI: | 10.1039/D5CC00672D |
| Online Access: | Verlag, kostenfrei, Volltext: https://doi.org/10.1039/D5CC00672D Verlag, kostenfrei, Volltext: https://pubs.rsc.org/en/content/articlelanding/2025/cc/d5cc00672d 
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| Author Notes: | Erik Misselwitz, Jonas Spengler, Frank Rominger and Milan Kivala |
| Summary: | Octacyanated tridecacyclene was synthesized from novel brominated tridecacyclene. In the crystal, the saddle-shaped scaffold exhibits a zigzag packing motif governed by an interplay between the inherent geometry of the central cyclooctatetraene moiety and the hydrogen bonding mediated by the dipolar cyano functionalities. The compound undergoes five reversible reductions in a particularly narrow potential window of 1.15 V in CH2Cl2. The first reduction occurs at −0.78 V (vs. Fc/Fc+), which corresponds to a remarkably low-lying LUMO of −4.32 eV. |
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| Item Description: | Zuerst veröffentlicht: 10. März 2025 Gesehen am 26.09.2025 |
| Physical Description: | Online Resource |
| ISSN: | 1364-548X |
| DOI: | 10.1039/D5CC00672D |