Karam Asad , Ruben Canton-Vitoria , Andreas Kourtellaris , Nikos Chronakis , Nikos Tagmatarchis
{"title":"新的顺式-2ʹ氮杂烯双加合物的拴定向区域选择性合成","authors":"Karam Asad , Ruben Canton-Vitoria , Andreas Kourtellaris , Nikos Chronakis , Nikos Tagmatarchis","doi":"10.1016/j.carbon.2024.119377","DOIUrl":null,"url":null,"abstract":"<div><p>Embarking into unexplored realms beyond the <em>C</em><sub><em>1</em></sub> <em>equatorial</em><sub><em>-face</em></sub> and <em>C</em><sub><em>1</em></sub> <em>trans</em>-4<em>′</em> regioisomers, this study delves into the synthesis of <em>cis</em>-2ʹ C<sub>59</sub>N bisadducts. The synthesis involves a two-step process. Firstly, a Mannich-type reaction between bisazafullerene (C<sub>59</sub>N)<sub>2</sub> and a tether yields a monoadduct. Further Bingel-Hirsch cyclopropanation results in the formation of the desired <em>cis</em>-2ʹ C<sub>59</sub>N bisadducts. Comprehensive spectroscopic techniques, including polarimetry and X-ray crystallography, confirm the absolute configuration (<sup><em>f,s</em></sup><em>clockwise</em> or <sup><em>f,s</em></sup><em>anticlockwise</em>) of the enantiomerically pure <em>cis</em>-2ʹ C<sub>59</sub>N bisadducts. Circular dichroism measurements revealed the extremely high chiroptical activity of these inherently chiral bisadducts. Evaluation of their optoelectronic properties through Vis-NIR absorption, PL emission, and cyclic voltammetry techniques reveals distinctive bandgap and NIR emission, ranging from 1.31 to 1.81 eV and 700–1108 nm, respectively, showcasing promising potential for applications in energy conversion.</p></div>","PeriodicalId":262,"journal":{"name":"Carbon","volume":null,"pages":null},"PeriodicalIF":10.5000,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Tether-directed regioselective synthesis of new cis-2ʹ azafullerene bisadducts\",\"authors\":\"Karam Asad , Ruben Canton-Vitoria , Andreas Kourtellaris , Nikos Chronakis , Nikos Tagmatarchis\",\"doi\":\"10.1016/j.carbon.2024.119377\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Embarking into unexplored realms beyond the <em>C</em><sub><em>1</em></sub> <em>equatorial</em><sub><em>-face</em></sub> and <em>C</em><sub><em>1</em></sub> <em>trans</em>-4<em>′</em> regioisomers, this study delves into the synthesis of <em>cis</em>-2ʹ C<sub>59</sub>N bisadducts. The synthesis involves a two-step process. Firstly, a Mannich-type reaction between bisazafullerene (C<sub>59</sub>N)<sub>2</sub> and a tether yields a monoadduct. Further Bingel-Hirsch cyclopropanation results in the formation of the desired <em>cis</em>-2ʹ C<sub>59</sub>N bisadducts. Comprehensive spectroscopic techniques, including polarimetry and X-ray crystallography, confirm the absolute configuration (<sup><em>f,s</em></sup><em>clockwise</em> or <sup><em>f,s</em></sup><em>anticlockwise</em>) of the enantiomerically pure <em>cis</em>-2ʹ C<sub>59</sub>N bisadducts. Circular dichroism measurements revealed the extremely high chiroptical activity of these inherently chiral bisadducts. Evaluation of their optoelectronic properties through Vis-NIR absorption, PL emission, and cyclic voltammetry techniques reveals distinctive bandgap and NIR emission, ranging from 1.31 to 1.81 eV and 700–1108 nm, respectively, showcasing promising potential for applications in energy conversion.</p></div>\",\"PeriodicalId\":262,\"journal\":{\"name\":\"Carbon\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":10.5000,\"publicationDate\":\"2024-06-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Carbon\",\"FirstCategoryId\":\"88\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0008622324005967\",\"RegionNum\":2,\"RegionCategory\":\"材料科学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Carbon","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0008622324005967","RegionNum":2,"RegionCategory":"材料科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
Tether-directed regioselective synthesis of new cis-2ʹ azafullerene bisadducts
Embarking into unexplored realms beyond the C1equatorial-face and C1trans-4′ regioisomers, this study delves into the synthesis of cis-2ʹ C59N bisadducts. The synthesis involves a two-step process. Firstly, a Mannich-type reaction between bisazafullerene (C59N)2 and a tether yields a monoadduct. Further Bingel-Hirsch cyclopropanation results in the formation of the desired cis-2ʹ C59N bisadducts. Comprehensive spectroscopic techniques, including polarimetry and X-ray crystallography, confirm the absolute configuration (f,sclockwise or f,santiclockwise) of the enantiomerically pure cis-2ʹ C59N bisadducts. Circular dichroism measurements revealed the extremely high chiroptical activity of these inherently chiral bisadducts. Evaluation of their optoelectronic properties through Vis-NIR absorption, PL emission, and cyclic voltammetry techniques reveals distinctive bandgap and NIR emission, ranging from 1.31 to 1.81 eV and 700–1108 nm, respectively, showcasing promising potential for applications in energy conversion.
期刊介绍：
The journal Carbon is an international multidisciplinary forum for communicating scientific advances in the field of carbon materials. It reports new findings related to the formation, structure, properties, behaviors, and technological applications of carbons. Carbons are a broad class of ordered or disordered solid phases composed primarily of elemental carbon, including but not limited to carbon black, carbon fibers and filaments, carbon nanotubes, diamond and diamond-like carbon, fullerenes, glassy carbon, graphite, graphene, graphene-oxide, porous carbons, pyrolytic carbon, and other sp2 and non-sp2 hybridized carbon systems. Carbon is the companion title to the open access journal Carbon Trends. Relevant application areas for carbon materials include biology and medicine, catalysis, electronic, optoelectronic, spintronic, high-frequency, and photonic devices, energy storage and conversion systems, environmental applications and water treatment, smart materials and systems, and structural and thermal applications.
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