Chang Wang, Chenyu Hu, Weize Wang, Jun Yang, Junzhi Liu
{"title":"五庚烯结构的合成:环戊并[ef]庚二烯到菲的重排","authors":"Chang Wang, Chenyu Hu, Weize Wang, Jun Yang, Junzhi Liu","doi":"10.31635/ccschem.024.202404765","DOIUrl":null,"url":null,"abstract":"<p>Novel carbon allotropes have long been pursued in synthetic chemistry and materials science, and graphene has been the most well-investigated carbon nanostructure in the past decade. However, an analogous carbon pentaheptite with equal numbers of pentagons and heptagons has not yet been synthesized because designing and synthesizing nonhexagon motifs along two dimensions is challenging. During the synthesis of a pentaheptite substructure (or named nanopentaheptite, <b xmlns:bkstg=\"http://www.atypon.com/backstage-ns\" xmlns:fn=\"http://www.w3.org/2005/xpath-functions\" xmlns:pxje=\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\" xmlns:urlutil=\"java:com.atypon.literatum.customization.UrlUtil\" xmlns:xlink=\"http://www.w3.org/1999/xlink\">\n<bold>NPH</bold></b>), which contain four pentagon-heptagon pairs and one heptalene unit, unexpected cyclopenta[<i>ef</i>]heptalene-into-phenanthrene rearrangements were observed for the first time, yielding two novel compounds (<b xmlns:bkstg=\"http://www.atypon.com/backstage-ns\" xmlns:fn=\"http://www.w3.org/2005/xpath-functions\" xmlns:pxje=\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\" xmlns:urlutil=\"java:com.atypon.literatum.customization.UrlUtil\" xmlns:xlink=\"http://www.w3.org/1999/xlink\">\n<bold>NPH-R1</bold></b> and <b xmlns:bkstg=\"http://www.atypon.com/backstage-ns\" xmlns:fn=\"http://www.w3.org/2005/xpath-functions\" xmlns:pxje=\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\" xmlns:urlutil=\"java:com.atypon.literatum.customization.UrlUtil\" xmlns:xlink=\"http://www.w3.org/1999/xlink\">\n<bold>NPH-R2</bold></b>). Experimental and theoretical results demonstrated that the <b xmlns:bkstg=\"http://www.atypon.com/backstage-ns\" xmlns:fn=\"http://www.w3.org/2005/xpath-functions\" xmlns:pxje=\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\" xmlns:urlutil=\"java:com.atypon.literatum.customization.UrlUtil\" xmlns:xlink=\"http://www.w3.org/1999/xlink\">\n<bold>NPH</bold></b> series exhibits narrower energy gaps than that of their hexagonal analog with similar size (e.g., hexa-peri-hexabenzocoronene, <b xmlns:bkstg=\"http://www.atypon.com/backstage-ns\" xmlns:fn=\"http://www.w3.org/2005/xpath-functions\" xmlns:pxje=\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\" xmlns:urlutil=\"java:com.atypon.literatum.customization.UrlUtil\" xmlns:xlink=\"http://www.w3.org/1999/xlink\">\n<bold>HBC</bold></b>). Our work reported herein, based on the azulene chemistry, provides new insights into the preparation of novel carbon allotrope pentaheptite nanostructures.</p>","PeriodicalId":9810,"journal":{"name":"CCS Chemistry","volume":"79 1","pages":""},"PeriodicalIF":9.4000,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Toward the Synthesis of Pentaheptite Substructure: The Cyclopenta[ef]heptalene to Phenanthrene Rearrangement\",\"authors\":\"Chang Wang, Chenyu Hu, Weize Wang, Jun Yang, Junzhi Liu\",\"doi\":\"10.31635/ccschem.024.202404765\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>Novel carbon allotropes have long been pursued in synthetic chemistry and materials science, and graphene has been the most well-investigated carbon nanostructure in the past decade. However, an analogous carbon pentaheptite with equal numbers of pentagons and heptagons has not yet been synthesized because designing and synthesizing nonhexagon motifs along two dimensions is challenging. During the synthesis of a pentaheptite substructure (or named nanopentaheptite, <b xmlns:bkstg=\\\"http://www.atypon.com/backstage-ns\\\" xmlns:fn=\\\"http://www.w3.org/2005/xpath-functions\\\" xmlns:pxje=\\\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\\\" xmlns:urlutil=\\\"java:com.atypon.literatum.customization.UrlUtil\\\" xmlns:xlink=\\\"http://www.w3.org/1999/xlink\\\">\\n<bold>NPH</bold></b>), which contain four pentagon-heptagon pairs and one heptalene unit, unexpected cyclopenta[<i>ef</i>]heptalene-into-phenanthrene rearrangements were observed for the first time, yielding two novel compounds (<b xmlns:bkstg=\\\"http://www.atypon.com/backstage-ns\\\" xmlns:fn=\\\"http://www.w3.org/2005/xpath-functions\\\" xmlns:pxje=\\\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\\\" xmlns:urlutil=\\\"java:com.atypon.literatum.customization.UrlUtil\\\" xmlns:xlink=\\\"http://www.w3.org/1999/xlink\\\">\\n<bold>NPH-R1</bold></b> and <b xmlns:bkstg=\\\"http://www.atypon.com/backstage-ns\\\" xmlns:fn=\\\"http://www.w3.org/2005/xpath-functions\\\" xmlns:pxje=\\\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\\\" xmlns:urlutil=\\\"java:com.atypon.literatum.customization.UrlUtil\\\" xmlns:xlink=\\\"http://www.w3.org/1999/xlink\\\">\\n<bold>NPH-R2</bold></b>). Experimental and theoretical results demonstrated that the <b xmlns:bkstg=\\\"http://www.atypon.com/backstage-ns\\\" xmlns:fn=\\\"http://www.w3.org/2005/xpath-functions\\\" xmlns:pxje=\\\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\\\" xmlns:urlutil=\\\"java:com.atypon.literatum.customization.UrlUtil\\\" xmlns:xlink=\\\"http://www.w3.org/1999/xlink\\\">\\n<bold>NPH</bold></b> series exhibits narrower energy gaps than that of their hexagonal analog with similar size (e.g., hexa-peri-hexabenzocoronene, <b xmlns:bkstg=\\\"http://www.atypon.com/backstage-ns\\\" xmlns:fn=\\\"http://www.w3.org/2005/xpath-functions\\\" xmlns:pxje=\\\"java:com.atypon.frontend.services.impl.PassportXslJavaExtentions\\\" xmlns:urlutil=\\\"java:com.atypon.literatum.customization.UrlUtil\\\" xmlns:xlink=\\\"http://www.w3.org/1999/xlink\\\">\\n<bold>HBC</bold></b>). Our work reported herein, based on the azulene chemistry, provides new insights into the preparation of novel carbon allotrope pentaheptite nanostructures.</p>\",\"PeriodicalId\":9810,\"journal\":{\"name\":\"CCS Chemistry\",\"volume\":\"79 1\",\"pages\":\"\"},\"PeriodicalIF\":9.4000,\"publicationDate\":\"2024-10-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"CCS Chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.31635/ccschem.024.202404765\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"CCS Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.31635/ccschem.024.202404765","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Toward the Synthesis of Pentaheptite Substructure: The Cyclopenta[ef]heptalene to Phenanthrene Rearrangement
Novel carbon allotropes have long been pursued in synthetic chemistry and materials science, and graphene has been the most well-investigated carbon nanostructure in the past decade. However, an analogous carbon pentaheptite with equal numbers of pentagons and heptagons has not yet been synthesized because designing and synthesizing nonhexagon motifs along two dimensions is challenging. During the synthesis of a pentaheptite substructure (or named nanopentaheptite, NPH), which contain four pentagon-heptagon pairs and one heptalene unit, unexpected cyclopenta[ef]heptalene-into-phenanthrene rearrangements were observed for the first time, yielding two novel compounds (NPH-R1 and NPH-R2). Experimental and theoretical results demonstrated that the NPH series exhibits narrower energy gaps than that of their hexagonal analog with similar size (e.g., hexa-peri-hexabenzocoronene, HBC). Our work reported herein, based on the azulene chemistry, provides new insights into the preparation of novel carbon allotrope pentaheptite nanostructures.
期刊介绍:
CCS Chemistry, the flagship publication of the Chinese Chemical Society, stands as a leading international chemistry journal based in China. With a commitment to global outreach in both contributions and readership, the journal operates on a fully Open Access model, eliminating subscription fees for contributing authors. Issued monthly, all articles are published online promptly upon reaching final publishable form. Additionally, authors have the option to expedite the posting process through Immediate Online Accepted Article posting, making a PDF of their accepted article available online upon journal acceptance.