The precision synthesis of helical bilayer nanographenes (NGs) with new topology is of substantial interest because of their exotic physicochemical properties. However, helical bilayer NGs bearing non-hexagonal rings remain synthetically challenging. Here we present the efficient synthesis of the first helical bilayer nonbenzenoid nanographene (HBNG1) from a tailor-made azulene-embedded precursor, which contains a novel [10]helicene backbone with two embedded heptagons. Single-crystal X-ray analysis reveals its highly twisted bilayer geometry with a record small interlayer distance of 3.2 Å among the reported helical bilayer NGs. Notably, the close interlayer distance between the two layers offers intramolecular through-space conjugation as revealed by in situ spectroelectrochemistry studies together with DFT simulations. Furthermore, the chiroptical properties of the P/M enantiomers of HBNG1 are also evaluated by circular dichroism and circularly polarized luminescence.
| Identifer | oai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:89511 |
| Date | 22 April 2024 |
| Creators | Yang, Lin, Ju, Yang-Yang, Medel, Miguel A., Fu, Yubin, Komber, Hartmut, Dmitrieva, Evgenia, Zhang, Jin-Jiang, Obermann, Sebastian, Campaña, Araceli G., Ma, Ji, 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, e202216193, 10.1002/anie.202216193, urn:nbn:de:bsz:14-qucosa2-889664, qucosa:88966, 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 | MSCA-ITN-ETN/813036//Bottom-Up generation of atomicalLy precise syntheTIc 2D MATerials for high performance in energy and Electronic applications – A multi-site innovative training action/ULTIMATE, 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/EnhanTopo/429265950//Untersuchung synthetischer Ansätze für nicht-alternierende ring topologien in Graphen Nanostrukturen |
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