Herein, we demonstrate a novel one-pot synthetic method towards a series of boron-doped polycyclic aromatic hydrocarbons (B-PAHs, 1 a–1 o), including hitherto unknown B-doped zethrene derivatives, from ortho-aryl substituted diarylalkynes with high atom efficiency and broad substrate scopes. A reaction mechanism is proposed based on the experimental investigation together with the theoretical calculations, which involves a unique 1,4-boron migration process. The resultant benchtop-stable B-PAHs are thoroughly investigated by X-ray crystallography, cyclic voltammetry, UV/Vis absorption, and fluorescence spectroscopies. The blue and green organic light-emitting diode (OLED) devices based on 1 f and 1 k are further fabricated, demonstrating the promising application potential of B-PAHs in organic optoelectronics.
| Identifer | oai:union.ndltd.org:DRESDEN/oai:qucosa:de:qucosa:91059 |
| Date | 17 May 2024 |
| Creators | Zhang, Jin-Jiang, Tang, Man-Chung, Fu, Yubin, Low, Kam-Hung, Ma, Ji, Yang, Lin, Weigand, Jan J., Liu, Junzhi, Wing-Wah Yam, Vivian, 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 | 1433-7851, 10.1002/anie.202011237, info:eu-repo/grantAgreement/European Commission/H2020 | SGA-RIA/881603//Graphene Flagship Core Project 3/GrapheneCore3, 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 | ERC | ERC-COG/819698//Development of Thiophene Based Conjugated Polymers in Two Dimensions/T2DCP, info:eu-repo/grantAgreement/Deutsche Forschungsgemeinschaft/EXC 1056/194636624//Center for Advancing Electronics Dresden/cfaed, info:eu-repo/grantAgreement/Deutsche Forschungsgemeinschaft/Sachbeihilfen/391979941//Erkundung von Heteroaromatischen und -antiaromatischen atompräzisen Nanographenen/EnhanceNano, info:eu-repo/grantAgreement/Deutsche Forschungsgemeinschaft/Sachbeihilfen/429265950//Untersuchung synthetischer Ansätze für nicht-alternierende ring topologien in Graphen Nanostrukturen/EnhanTopo |
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