Open-shell non-alternant polycyclic hydrocarbons (PHs) are attracting increasing attention due to their promising applications in organic spintronics and quantum computing. Herein we report the synthesis of three cyclohepta[def]fluorene-based diradicaloids (1–3), by fusion of benzo rings on its periphery for the thermodynamic stabilization, as evidenced by multiple characterization techniques. Remarkably, all of them display a very narrow optical energy gap (Egopt=0.52–0.69 eV) and persistent stability under ambient conditions (t1/2=11.7–33.3 h). More importantly, this new type of diradicaloids possess a low-lying triplet state with an extremely small singlet–triplet energy gap, as low as 0.002 kcal mol−1, with a clear dependence on the molecular size. This family of compounds thus offers a new route to create non-alternant open-shell PHs with high-spin ground states, and opens up novel possibilities and insights into understanding the structure–property relationships.
| Identifer | oai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:89670 |
| Date | 22 April 2024 |
| Creators | Wu, Fupeng, Ma, Ji, Lombardi, Federico, Fu, Yubin, Liu, Fupin, Huang, Zhijie, Liu, Renxiang, Komber, Hartmut, Alexandropoulos, Dimitris I., Dmitrieva, Evgenia, Lohr, Thorsten G., Israel, Noel, Popov, Alexey A., Liu, Junzhi, Bogani, Lapo, Feng, Xinliang |
| Publisher | Wiley-VCH |
| Source Sets | Hochschulschriftenserver (HSSS) der SLUB Dresden |
| Language | English |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, doc-type:article, info:eu-repo/semantics/article, doc-type:Text |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 1521-3773, e202202170, 10.1002/anie.202202170, info:eu-repo/grantAgreement/European Commission/H2020 | SGA-RIA/881603//Graphene Flagship Core Project 3/GrapheneCore3, info:eu-repo/grantAgreement/European Commission/H2020 | ERC | ERC-COG/819698//Development of Thiophene Based Conjugated Polymers in Two Dimensions/T2DCP, info:eu-repo/grantAgreement/European Commission/H2020 | RIA/101017821//MULTI-ELECTRON PROCESSES FOR LIGHT DRIVEN ELECTRODES AND ELECTROLYTES IN CONVERSION AND STORAGE OF SOLAR ENERGY/LIGHT-CAP, info:eu-repo/grantAgreement/Deutsche Forschungsgemeinschaft/DFG-SNSF Joint Switzerland-German Research Project/429265950//Untersuchung synthetischer Ansätze für nicht-alternierende ring topologien in Graphen Nanostrukturen/EnhanTopo, info:eu-repo/grantAgreement/European Commission/H2020 | ERC | ERC-COG/773048//Molecular Magnetic Graphene Nanoribbons/MMGNRs |
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