Manuel Buendía , Anton J. Stasyuk , Salvatore Filippone , Miquel Solà , Nazario Martín
{"title":"All-carbon supramolecular complexation of a bilayer molecular nanographene with [60] and [70]fullerenes†","authors":"Manuel Buendía , Anton J. Stasyuk , Salvatore Filippone , Miquel Solà , Nazario Martín","doi":"10.1039/d4qo02071e","DOIUrl":null,"url":null,"abstract":"<div><div>Supramolecular chemistry of carbon-based materials provides a variety of chemical structures with potential applications in materials science and biomedicine. Here, we explore the supramolecular complexation of fullerenes C<sub>60</sub> and C<sub>70</sub>, highlighting the ability of molecular nanographene tweezers to capture these structures. The binding constant for the complex was significantly higher than for , showing a clear selectivity for the more π-extended C<sub>70</sub>. DFT calculations confirmed these experimental results by showing that the interaction energy of C<sub>70</sub> with is more than 5 kcal mol<sup>−1</sup> higher than that of C<sub>60</sub>. Theoretical calculations predict that the dispersion interaction provides about 58–59% of the total interaction energy, followed by electrostatic attraction with 26% and orbital interactions, which contribute 15–16%. The racemic nanographene tweezers effectively recognize fullerene molecules and hold promise for future applications in chiral molecule recognition.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 5","pages":"Pages 1438-1443"},"PeriodicalIF":0.0000,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/qo/d4qo02071e?page=search","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412924008866","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Supramolecular chemistry of carbon-based materials provides a variety of chemical structures with potential applications in materials science and biomedicine. Here, we explore the supramolecular complexation of fullerenes C60 and C70, highlighting the ability of molecular nanographene tweezers to capture these structures. The binding constant for the complex was significantly higher than for , showing a clear selectivity for the more π-extended C70. DFT calculations confirmed these experimental results by showing that the interaction energy of C70 with is more than 5 kcal mol−1 higher than that of C60. Theoretical calculations predict that the dispersion interaction provides about 58–59% of the total interaction energy, followed by electrostatic attraction with 26% and orbital interactions, which contribute 15–16%. The racemic nanographene tweezers effectively recognize fullerene molecules and hold promise for future applications in chiral molecule recognition.