On-Surface Synthesis of a π-Extended Diaza[8]circulene
Heterocyclic [8]circulenes are an important class of polycyclic aromatic hydrocarbon molecules because of their unique structural properties and promising applications. However, the synthesis of heterocyclic [8]circulenes is still limited and thus is an important synthetic challenge. Here we describ...
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sg-ntu-dr.10356-1519062022-06-21T02:31:23Z On-Surface Synthesis of a π-Extended Diaza[8]circulene Nakamura, Kimihiro Li, Qiang-Qiang Krejčí, Ondřej Foster, Adam S. Sun, Kewei Kawai, Shigeki Ito, Shingo School of Physical and Mathematical Sciences Science::Chemistry Hydrocarbons Molecules Heterocyclic [8]circulenes are an important class of polycyclic aromatic hydrocarbon molecules because of their unique structural properties and promising applications. However, the synthesis of heterocyclic [8]circulenes is still limited and thus is an important synthetic challenge. Here we describe the first example of a π-extended diaza[8]circulene surrounded by and fused with six hexagons and two pentagons, which was successfully synthesized only by a combined in-solution and on-surface synthetic strategy. State-of-the-art scanning tunneling microscopy with a CO-functionalized tip and density functional theory calculations revealed its planar conformation and unique electronic structure. Ministry of Education (MOE) Nanyang Technological University This work was supported in part by Nanyang Technological University (S.I.), the Singapore Ministry of Education via Academic Research Fund Tier 1:2018-T1-002-021 (S.I.), and Japan Society for the Promotion of Science (JSPS) through KAKENHI Grant 19H00856 (S.K.). K.N. thanks NTU for the SPMS International Internship Program. O.K. was supported by the European Union’s Horizon 2020 Research and Innovation Programme under Marie Skłodowska-Curie Grant Agreement 845060. A.S.F. was supported by the World Premier International Research Center Initiative (WPI), MEXT, Japan. Computing resources from the Aalto ScienceIT Project and CSC, Helsinki, are gratefully acknowledged. S.K. sincerely thanks Prof. Ernst Meyer, Dr. Urs Gysin, Mr. Sascha Martin, and Mr. Yves Pellmont for their support to build the low-temperature ultrahigh-vacuum atomic force microscopy/scanning tunneling microscopy system. S.I. sincerely thanks Prof. Rei Kinjo and Ms. Kei Ota (NTU) for ACID analysis and Prof. Naoki Aratani (NAIST) for the fruitful discussion during the preparation of this Communication. 2021-07-26T02:49:44Z 2021-07-26T02:49:44Z 2020 Journal Article Nakamura, K., Li, Q., Krejčí, O., Foster, A. S., Sun, K., Kawai, S. & Ito, S. (2020). On-Surface Synthesis of a π-Extended Diaza[8]circulene. Journal of the American Chemical Society, 142(26), 11363-11369. https://dx.doi.org/10.1021/jacs.0c02534 0002-7863 https://hdl.handle.net/10356/151906 10.1021/jacs.0c02534 32413264 2-s2.0-85085659729 26 142 11363 11369 en 2018-T1-002-021 Journal of the American Chemical Society 10.21979/N9/ZA778V © 2020 American Chemical Society. All rights reserved. |
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Science::Chemistry Hydrocarbons Molecules Nakamura, Kimihiro Li, Qiang-Qiang Krejčí, Ondřej Foster, Adam S. Sun, Kewei Kawai, Shigeki Ito, Shingo On-Surface Synthesis of a π-Extended Diaza[8]circulene |
| description |
Heterocyclic [8]circulenes are an important class of polycyclic aromatic hydrocarbon molecules because of their unique structural properties and promising applications. However, the synthesis of heterocyclic [8]circulenes is still limited and thus is an important synthetic challenge. Here we describe the first example of a π-extended diaza[8]circulene surrounded by and fused with six hexagons and two pentagons, which was successfully synthesized only by a combined in-solution and on-surface synthetic strategy. State-of-the-art scanning tunneling microscopy with a CO-functionalized tip and density functional theory calculations revealed its planar conformation and unique electronic structure. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Nakamura, Kimihiro Li, Qiang-Qiang Krejčí, Ondřej Foster, Adam S. Sun, Kewei Kawai, Shigeki Ito, Shingo |
| format |
Article |
| author |
Nakamura, Kimihiro Li, Qiang-Qiang Krejčí, Ondřej Foster, Adam S. Sun, Kewei Kawai, Shigeki Ito, Shingo |
| author_sort |
Nakamura, Kimihiro |
| title |
On-Surface Synthesis of a π-Extended Diaza[8]circulene |
| title_short |
On-Surface Synthesis of a π-Extended Diaza[8]circulene |
| title_full |
On-Surface Synthesis of a π-Extended Diaza[8]circulene |
| title_fullStr |
On-Surface Synthesis of a π-Extended Diaza[8]circulene |
| title_full_unstemmed |
On-Surface Synthesis of a π-Extended Diaza[8]circulene |
| title_sort |
on-surface synthesis of a π-extended diaza[8]circulene |
| publishDate |
2021 |
| url |
https://hdl.handle.net/10356/151906 |
| _version_ |
1736856356502110208 |