On-Surface Stereochemical Characterization of a Highly Curved Chiral Nanographene by Noncontact Atomic Force Microscopy and Scanning Tunneling Microscopy  

作　　者：Qigang Zhong Viktor Barat Daniel Csokas Kaifeng Niu Marcin Gorecki Animesh Ghosh Jonas Bjork Daniel Ebeling Lifeng Chi Andre Schirmeisen Mihaiela C.Stuparu 

机构地区：[1]Institute of Applied Physics,Center for Materials Research(LaMa),Justus-Liebig University Giessen,35392 Giessen [2]School of Chemistry,Chemical Engineering and Biotechnology,Nanyang Technological University,637371 Singapore [3]Institute of Organic Chemistry,Research Center for Natural Sciences,H-1117 Budapest [4]Jiangsu Key Laboratory for Carbon-Based Functional Materials and Devices,Institute of Functional Nano and Soft Materials,Soochow University,215123 Suzhou [5]Department of Physics,Chemistry and Biology,IFM,Linkoping University,58183 Linkoping [6]Institute of Organic Chemistry,Polish Academy of Sciences,01-224 Warsaw [7]Macao Institute of Materials Science and Engineering(MIMSE),MUST-SUDA Joint Research Center for Advanced Functional Materials,Macao University of Science and Technology,Taipa 999078,Macao,China

出　　处：《CCS Chemistry》2023年第12期2888-2896,共9页中国化学会会刊（英文）

基　　金：Financial support from the Ministry of Education Singapore under the AcRF Tier 1(MOE T1 RG11/21)and AcRF Tier 2(MOE-T2EP10221-0002);The Deutsche Forschungsgemeinschaft via grants(nos.SCHI 619/13 and EB535/1-1);the GRK(Research Training Group)2204“Substitute Materials for Sustainable Energy Technologies”;the LOEWE Program of Excellence of the Federal State of Hesse(LOEWE Focus Group PriOSS“Principles of On-Surface Synthesis”);the National Natural Science Foundation of China(grant nos.21790053,51821002,and 22072103);the National Major State Basic Research Development Program of China(grant nos.2017YFA0205000 and 2017YFA0205002);the Collaborative Innovation Center of Suzhou Nano Science&Technology;the 111 Project are also acknowledged for their financial support.

摘　　要：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 noncontact 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.

关 键 词：chirality at surfaces noncontact atomic force microscopy scanning tunnelling microscopy submolecular resolution imaging single-bond resolution curved nanographenes multiple helicenes chiral nanostructures bowl-helix hybrids scanning probe microscopy 

分 类 号：O62[理学—有机化学]