Publication
Strain‐Sensitive On‐Surface Ladderization by Non‐Dehydrogenative Heterocyclization
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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- 21/12/2022
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- Accepted manuscript
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20221220 Chem EU Ma_EuroJPhysChem_SI.pdf | 3.46 MB | MDR Open |
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20221220 Heterocyclidization_Main_manuscript_Word_version.docx | 918 KB | MDR Open |
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