Mechanistical Study on Substrate‐Controlled Highly Selective [2+2] and [2+3] Cycloaddition Reactions

Polycyclic conjugated hydrocarbons have acquired increased interests recently because of their potential applications in electronic devices. On metal surfaces, the selective synthesis of four- and five-membered carbon rings remains challenging due to the presence of diverse reaction pathways. Here, utilizing the same precursor molecule, we successfully achieved substrate-controlled highly selective cycloaddition reactions towards four- and five-membered carbon rings. A 97 % yield for four-membered carbon rings on Au(111), while a 96 % yield towards five-membered carbon rings is achieved on Ag(111). The detailed topological structures of the reaction products are carefully examined by bond-resolving scanning tunneling microscopy (BR-STM) imaging with a CO functionalized tip. The underlying mechanism of the novel surface-directed reaction selectivity is elucidated by extensive density functional theory (DFT) calculations. Our study paves the way for high selective synthesis of polycyclic conjugated hydrocarbons with non-benzenoid rings.

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Publication Details

Journal
Chemistry - A European Journal
Published
2024-11-29
DOI
https://doi.org/10.1002/chem.202404074
Citations
2
Primary Topic
Surface Chemistry and Catalysis
Type
article
Field-Weighted Citation Impact
0.37

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article

Mechanistical Study on Substrate‐Controlled Highly Selective [2+2] and [2+3] Cycloaddition Reactions

Jinming Cai, Huaming Zhu, Yong Zhang, Jonas Björk et al.
2 citations
Chemistry - A European Journal
Surface Chemistry and Catalysis
0.37
article

Mechanistical Study on Substrate‐Controlled Highly Selective [2+2] and [2+3] Cycloaddition Reactions

Jinming Cai, Huaming Zhu, Yong Zhang, Jonas Björk, Jianchen Lu, Haiping Lin, Kaifeng Niu, Johanna Rosén, Qing Li, Chuan Deng, Yi Zhang, Xinjing Zhao, Peipei Huang, Junbo Wang
article en
2 citations

Abstract

Polycyclic conjugated hydrocarbons have acquired increased interests recently because of their potential applications in electronic devices. On metal surfaces, the selective synthesis of four- and five-membered carbon rings remains challenging due to the presence of diverse reaction pathways. Here, utilizing the same precursor molecule, we successfully achieved substrate-controlled highly selective cycloaddition reactions towards four- and five-membered carbon rings. A 97 % yield for four-membered carbon rings on Au(111), while a 96 % yield towards five-membered carbon rings is achieved on Ag(111). The detailed topological structures of the reaction products are carefully examined by bond-resolving scanning tunneling microscopy (BR-STM) imaging with a CO functionalized tip. The underlying mechanism of the novel surface-directed reaction selectivity is elucidated by extensive density functional theory (DFT) calculations. Our study paves the way for high selective synthesis of polycyclic conjugated hydrocarbons with non-benzenoid rings.

Chemistry - A European JournalVol. 31(8)
Linköping University (SE), Kunming University of Science and Technology (CN), Huaqiao University (CN), Division of Materials Science and Engineering (AU), Materials Design (France) (FR), Shaanxi Normal University (CN)
National Natural Science Foundation of China, China Postdoctoral Science Foundation, Fundamental Research Funds for Central Universities of the Central South University
Openalex Percentile: Top 42%
Surface Chemistry and Catalysis
0.37
DOIOpen Access PDFOpenAlex
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