Download all files (8.15 MB)

Collection

Citation

Description:

On-surface synthesis became a powerful strategy to synthesize extended nanocarbon materials, such as oligomers and graphene nanoribbons, via C–C bond formation between small precursor molecules. However, the reverse reaction, namely C–C bond cleavage, remains challenging due to the high activation barrier. Here, we present systematic fragmentation to individual units from tetra(9-anthryl)benzene oligomers, which were synthesized by the Ullmann-type homocoupling on Au(111). The detailed mechanism of the fragmentation was investigated with a combination of scanning tunneling microscopy and density functional theory calculations. We found that the Diels-Alder reaction between anthracene groups in the unit significantly lowers the activation barrier to cleave the C–C bond between the units in the oligomer. Our findings may offer an approach to disassemble oligomers in a controlled manner.

Rights:

• Creative Commons BY Attribution 4.0 International
  

Keyword: on-surface synthesis, fragmentation, Diels-Alder reaction, scanning tunneling microscopy, density functional theory, oligonomers

Date published: 2025-10-14

Publisher: American Chemical Society (ACS)

Journal:

• ACS Nano (ISSN: 19360851) vol. 19 issue. 40 p. 35825-35832

Funding:

• Japan Society for the Promotion of Science 24K01454
• Japan Society for the Promotion of Science 24K21721
• Japan Society for the Promotion of Science 24KF0269
• Japan Society for the Promotion of Science 25H00422
• Eneos Tonegeneral research foundation

Manuscript type: Publisher's version (Version of record)

MDR DOI:

First published URL: https://doi.org/10.1021/acsnano.5c12424

Related item:

Other identifier(s):

Contact agent:

Updated at: 2025-10-21 16:06:44 +0900

Published on MDR: 2025-10-21 15:43:40 +0900