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On-surface cyclodehydrogenation recently became an important reaction to planarize π-conjugated molecules and oligomers. However, the high-activation barrier to cleave the C−H bond often requires high-temperature annealing, consequently restricting structures of precursor molecules and/or leading to random fusion at their edges. Here, we present a synthesis of pyrrolopyrrole-bridged ladder oligomers from 11,11,12,12-tetrabromo-1,4,5,8-tetraaza-9,10-anthraquinodimethane molecules on Ag(111) with bond-resolved scanning tunnelling microscopy. This non-dehydrogenative cyclization between pyrazine and ethynylene/cumulene groups has a low-activation barrier for forming intermediary dimeric oligomer containing dipyrazinopyrrolopyrrolopyrazine units, thus giving new insight into the strain-sensitive in ladder-oligomer formation.

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  This is the peer reviewed version of the following article: Strain‐Sensitive On‐Surface Ladderization by Non‐Dehydrogenative Heterocyclization, which has been published in final form at https://doi.org/10.1002/chem.202203622. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.

Keyword: on-surface ladderization, non‐dehydrogenative heterocyclization, strain-sensitive

Date published: 2023-03-13

Publisher: Wiley

Journal:

• Chemistry – A European Journal (ISSN: 15213765) vol. 29 issue. 15 e202203622

Funding:

• Japan Society for the Promotion of Science 20H02719
• Japan Society for the Promotion of Science 21K18885
• Japan Society for the Promotion of Science 21F21058
• Japan Society for the Promotion of Science 22H00285
• Japan Society for the Promotion of Science 20K21184
• Japan Society for the Promotion of Science 21H01912
• Japan Society for the Promotion of Science 21H05468

Manuscript type: Author's version (Accepted manuscript)

MDR DOI: https://doi.org/10.48505/nims.4365

First published URL: https://doi.org/10.1002/chem.202203622

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Updated at: 2024-01-25 11:15:37 +0900

Published on MDR: 2024-01-25 12:30:21 +0900