Muhammad Imran, Lin Yang, Jinjiang Zhang, Yubin Fu, Zhen-Lin Qiu, Noel Israel, Evgenia Dmitrieva, Gianluca Serra, Andrea Lucotti, Matteo Tommasini, Ji Ma, Xinliang Feng
{"title":"A Persistent Concealed Non-Kekulé Nanographene: Synthesis and in-situ Characterization","authors":"Muhammad Imran, Lin Yang, Jinjiang Zhang, Yubin Fu, Zhen-Lin Qiu, Noel Israel, Evgenia Dmitrieva, Gianluca Serra, Andrea Lucotti, Matteo Tommasini, Ji Ma, Xinliang Feng","doi":"10.1039/d4qo02019g","DOIUrl":null,"url":null,"abstract":"Concealed non-Kekulé (CNK) nanographenes have recently gained attention as promising non-Kekulé model systems due to their distinctive antiferromagnetic electronic spins, which offer potential applications in spintronics and quantum information science. However, synthesizing CNK nanographenes in solution remains a significant challenge because of their strong biradical character and high reactivity. In this study, we report the successful synthesis of a novel CNK nanographene with two phenalene units fused in a cis configuration to perylene (c-CNK), which exhibits persistent stability under ambient conditions, with a half-life (t1/2) of 59 minutes. The formation of the c-CNK is confirmed using in-situ UV-Vis-NIR spectroscopy, Raman spectroscopy, and high-resolution mass spectrometry. The open-shell character of c-CNK is supported by the electron paramagnetic resonance (EPR) spectroscopy by observing an isotropic signal with a g-value of 2.0026. Quantum chemical simulations reveal a high biradical character (y0 = 0.97) and a singlet open-shell ground state with a small singlet-triplet energy gap (ΔES-T) of 0.4 kcal/mol. This work presents a solution synthesis of a next-generation concealed non-Kekulé nanographene with intrinsic antiferromagnetic electronic spins, highlighting its potential as promising material for future quantum technologies.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"75 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo02019g","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
A Persistent Concealed Non-Kekulé Nanographene: Synthesis and in-situ Characterization
Concealed non-Kekulé (CNK) nanographenes have recently gained attention as promising non-Kekulé model systems due to their distinctive antiferromagnetic electronic spins, which offer potential applications in spintronics and quantum information science. However, synthesizing CNK nanographenes in solution remains a significant challenge because of their strong biradical character and high reactivity. In this study, we report the successful synthesis of a novel CNK nanographene with two phenalene units fused in a cis configuration to perylene (c-CNK), which exhibits persistent stability under ambient conditions, with a half-life (t1/2) of 59 minutes. The formation of the c-CNK is confirmed using in-situ UV-Vis-NIR spectroscopy, Raman spectroscopy, and high-resolution mass spectrometry. The open-shell character of c-CNK is supported by the electron paramagnetic resonance (EPR) spectroscopy by observing an isotropic signal with a g-value of 2.0026. Quantum chemical simulations reveal a high biradical character (y0 = 0.97) and a singlet open-shell ground state with a small singlet-triplet energy gap (ΔES-T) of 0.4 kcal/mol. This work presents a solution synthesis of a next-generation concealed non-Kekulé nanographene with intrinsic antiferromagnetic electronic spins, highlighting its potential as promising material for future quantum technologies.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.