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Helical Bilayer Nonbenzenoid Nanographene Bearing a [10]Helicene with Two Embedded Heptagons

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.

Identiferoai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:89511
Date22 April 2024
CreatorsYang, 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
PublisherWiley-VCH
Source SetsHochschulschriftenserver (HSSS) der SLUB Dresden
LanguageEnglish
Detected LanguageEnglish
Typeinfo:eu-repo/semantics/publishedVersion, doc-type:article, info:eu-repo/semantics/article, doc-type:Text
Rightsinfo:eu-repo/semantics/openAccess
Relation1521-3773, 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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