On-Surface Stereochemical Characterization of a Highly Curved Chiral Nanographene by Noncontact Atomic Force Microscopy and Scanning Tunneling MicroscopyShow others and affiliations
2023 (English)In: CCS CHEMISTRY, ISSN 2096-5745, Vol. 5, no 12, p. 2888-2896Article in journal (Refereed) Published
Abstract [en]
A highly distorted chiral nanographene structure composed of triple corannulene-fused [5]helicenes is prepared with the help of the Heck reaction and oxidative photocyclization with an overall isolated yield of 28%. The complex three-dimensional (3D) structure of the bowl-helix hybrid nanostructure is studied by a combination of non contact atomic force microscopy (AFM) and scanning tunneling microscopy (STM) on the Cu(111) surface, density functional theory calculations, AFM/STM simulations, and high-performance liquid chromatography-electronic circular dichroism analysis. This examination reveals a molecular structure in which the three bowl-shaped corannulene bladesd position themselves in a C3-symmetric fashion around a highly twisted triphenylene core. The molecule appears to be shaped like a propeller in which the concave side of the bowls face away from the connected [5]helicene motif. The chirality of the nanostructure is confirmed by the direct visualization of both MMM and PPP enantiomers at the single-molecule level by scanning probe microscopies. These results underline that submolecular resolution imaging by AFM/STM is a powerful real-space tool for the stereochemical characterization of 3D curved chiral nanographene structures.
Place, publisher, year, edition, pages
CHINESE CHEMICAL SOC , 2023. Vol. 5, no 12, p. 2888-2896
Keywords [en]
chirality at surfaces; noncontact atomicforce microscopy; scanning tunnelling microscopy; submolecular resolution imaging; single-bond resolution; curved nanographenes; multiple helicenes; chiralnanostructures; bowl-helix hybrids; scanning probe microscopy
National Category
Inorganic Chemistry
Identifiers
URN: urn:nbn:se:liu:diva-197464DOI: 10.31635/ccschem.023.202303065ISI: 001053229000001OAI: oai:DiVA.org:liu-197464DiVA, id: diva2:1794556
Note
Funding Agencies|Ministry of Education [MOE-T2EP10221-0002]; AcRF Tier 2 [SCHI 619/13]; Ministry of Education Singapore [MOE-T2EP10221-0002, MOE T1 RG11/21]; Deutsche Forschungsgemeinschaft [SCHI 619/13, EB535/1-1]; RK (Research Training Group) 2204 "Substitute Materials for Sustainable Energy Technologies"; LOEWE Program of Excellence of the Federal State of Hesse (LOEWE Focus Group PriOSS "Principles of On-Surface Synthesis"); National Natural Science Foundation of China [21790053, 51821002, 22072103]; National Major State Basic Research Development Program of China [2017YFA0205000, 2017YFA0205002]; Collaborative Innovation Center of Suzhou Nano Science amp; Technology; 111 Project
2023-09-062023-09-062024-10-03Bibliographically approved