On-surface stereochemical characterization of a highly curved chiral nanographene by noncontact atomic force microscopy and scanning tunneling microscopy
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...
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sg-ntu-dr.10356-1729892024-01-12T15:32:13Z On-surface stereochemical characterization of a highly curved chiral nanographene by noncontact atomic force microscopy and scanning tunneling microscopy Zhong, Qigang Barát, Viktor Csókás, Dániel Niu, Kaifeng Górecki, Marcin Ghosh, Animesh Björk, Jonas Ebeling, Daniel Chi, Lifeng Schirmeisen, André Stuparu, Mihaiela Corina School of Chemistry, Chemical Engineering and Biotechnology Science::Chemistry Noncontact Atomic Force Microscopy Scanning Tunnelling Microscopy 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. Ministry of Education (MOE) Published version Financial support from the Ministry of Education Singa-pore under the AcRF Tier 1 (MOE T1 RG11/21) and AcRF Tier 2 (MOE-T2EP10221-0002) is acknowledged. The Deutsche Forschungsgemeinschaft via grants (nos. SCHI619/13 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, and the 111 Project are also acknowledged for their financial support. Computational resources were allocated at the National Supercomputer Centre, Sweden, by SNIC, and at the Wroclaw Centre for Networking and Supercomputing, Poland. 2024-01-08T02:54:27Z 2024-01-08T02:54:27Z 2023 Journal Article Zhong, Q., Barát, V., Csókás, D., Niu, K., Górecki, M., Ghosh, A., Björk, J., Ebeling, D., Chi, L., Schirmeisen, A. & Stuparu, M. C. (2023). On-surface stereochemical characterization of a highly curved chiral nanographene by noncontact atomic force microscopy and scanning tunneling microscopy. CCS Chemistry, 5(12), 2888-2896. https://dx.doi.org/10.31635/ccschem.023.202303065 2096-5745 https://hdl.handle.net/10356/172989 10.31635/ccschem.023.202303065 2-s2.0-85179043036 12 5 2888 2896 en MOE T1 RG11/21 MOE-T2EP10221-0002 CCS Chemistry © 2023 Chinese Chemical Society. This is an open-access article distributed under the terms of the Creative Commons License. application/pdf |
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Science::Chemistry Noncontact Atomic Force Microscopy Scanning Tunnelling Microscopy Zhong, Qigang Barát, Viktor Csókás, Dániel Niu, Kaifeng Górecki, Marcin Ghosh, Animesh Björk, Jonas Ebeling, Daniel Chi, Lifeng Schirmeisen, André Stuparu, Mihaiela Corina On-surface stereochemical characterization of a highly curved chiral nanographene by noncontact atomic force microscopy and scanning tunneling microscopy |
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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. |
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School of Chemistry, Chemical Engineering and Biotechnology |
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School of Chemistry, Chemical Engineering and Biotechnology Zhong, Qigang Barát, Viktor Csókás, Dániel Niu, Kaifeng Górecki, Marcin Ghosh, Animesh Björk, Jonas Ebeling, Daniel Chi, Lifeng Schirmeisen, André Stuparu, Mihaiela Corina |
format |
Article |
author |
Zhong, Qigang Barát, Viktor Csókás, Dániel Niu, Kaifeng Górecki, Marcin Ghosh, Animesh Björk, Jonas Ebeling, Daniel Chi, Lifeng Schirmeisen, André Stuparu, Mihaiela Corina |
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Zhong, Qigang |
title |
On-surface stereochemical characterization of a highly curved chiral nanographene by noncontact atomic force microscopy and scanning tunneling microscopy |
title_short |
On-surface stereochemical characterization of a highly curved chiral nanographene by noncontact atomic force microscopy and scanning tunneling microscopy |
title_full |
On-surface stereochemical characterization of a highly curved chiral nanographene by noncontact atomic force microscopy and scanning tunneling microscopy |
title_fullStr |
On-surface stereochemical characterization of a highly curved chiral nanographene by noncontact atomic force microscopy and scanning tunneling microscopy |
title_full_unstemmed |
On-surface stereochemical characterization of a highly curved chiral nanographene by noncontact atomic force microscopy and scanning tunneling microscopy |
title_sort |
on-surface stereochemical characterization of a highly curved chiral nanographene by noncontact atomic force microscopy and scanning tunneling microscopy |
publishDate |
2024 |
url |
https://hdl.handle.net/10356/172989 |
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1789483201883799552 |