Luca Camilli*, Conor Hogan*, Deborah Romito, Luca Persichetti, Antonio Caporale, Maurizia Palummo, Marco Di Giovannantonio and Davide Bonifazi*,
{"title":"由链烷键驱动的表面分子识别","authors":"Luca Camilli*, Conor Hogan*, Deborah Romito, Luca Persichetti, Antonio Caporale, Maurizia Palummo, Marco Di Giovannantonio and Davide Bonifazi*, ","doi":"10.1021/jacsau.4c00325","DOIUrl":null,"url":null,"abstract":"<p >Chalcogen bonding interactions (ChBIs) have been widely employed to create ordered noncovalent assemblies in solids and liquids. Yet, their ability to engineer molecular self-assembly on surfaces has not been demonstrated. Here, we report the first demonstration of on-surface molecular recognition solely governed by ChBIs. Scanning tunneling microscopy and <i>ab initio</i> calculations reveal that a pyrenyl derivative can undergo noncovalent chiral dimerization on the Au(111) surface through double Ch···N interactions involving Te- or Se-containing chalcogenazolo pyridine motifs. In contrast, reference chalcogenazole counterparts lacking the pyridyl moiety fail to form regular self-assemblies on Au, resulting in disordered assemblies.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":null,"pages":null},"PeriodicalIF":8.5000,"publicationDate":"2024-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00325","citationCount":"0","resultStr":"{\"title\":\"On-Surface Molecular Recognition Driven by Chalcogen Bonding\",\"authors\":\"Luca Camilli*, Conor Hogan*, Deborah Romito, Luca Persichetti, Antonio Caporale, Maurizia Palummo, Marco Di Giovannantonio and Davide Bonifazi*, \",\"doi\":\"10.1021/jacsau.4c00325\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Chalcogen bonding interactions (ChBIs) have been widely employed to create ordered noncovalent assemblies in solids and liquids. Yet, their ability to engineer molecular self-assembly on surfaces has not been demonstrated. Here, we report the first demonstration of on-surface molecular recognition solely governed by ChBIs. Scanning tunneling microscopy and <i>ab initio</i> calculations reveal that a pyrenyl derivative can undergo noncovalent chiral dimerization on the Au(111) surface through double Ch···N interactions involving Te- or Se-containing chalcogenazolo pyridine motifs. In contrast, reference chalcogenazole counterparts lacking the pyridyl moiety fail to form regular self-assemblies on Au, resulting in disordered assemblies.</p>\",\"PeriodicalId\":94060,\"journal\":{\"name\":\"JACS Au\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":8.5000,\"publicationDate\":\"2024-06-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00325\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"JACS Au\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/jacsau.4c00325\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"JACS Au","FirstCategoryId":"1085","ListUrlMain":"https://pubs.acs.org/doi/10.1021/jacsau.4c00325","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
摘要
钙原键相互作用(ChBIs)已被广泛用于在固体和液体中创建有序的非共价组装。然而,它们在表面进行分子自组装的能力尚未得到证实。在这里,我们首次报告了完全由 ChBIs 控制的表面分子识别能力。扫描隧道显微镜和 ab initio 计算显示,一种芘衍生物可以在 Au(111) 表面通过含 Te 或 Se 的醛基唑吡啶基团的双 Ch-N 相互作用进行非共价手性二聚化。与此相反,缺少吡啶基的醛基氮唑参照物无法在金上形成规则的自组装,从而导致无序组装。
On-Surface Molecular Recognition Driven by Chalcogen Bonding
Chalcogen bonding interactions (ChBIs) have been widely employed to create ordered noncovalent assemblies in solids and liquids. Yet, their ability to engineer molecular self-assembly on surfaces has not been demonstrated. Here, we report the first demonstration of on-surface molecular recognition solely governed by ChBIs. Scanning tunneling microscopy and ab initio calculations reveal that a pyrenyl derivative can undergo noncovalent chiral dimerization on the Au(111) surface through double Ch···N interactions involving Te- or Se-containing chalcogenazolo pyridine motifs. In contrast, reference chalcogenazole counterparts lacking the pyridyl moiety fail to form regular self-assemblies on Au, resulting in disordered assemblies.