Urgel, José I.; Bock, Julian; Di Giovannantonio, Marco; Ruffieux, Pascal; Pignedoli, Carlo A.; Kivala, Milan; Fasel, Roman (2021). On-surface synthesis of π-conjugated ladder-type polymers comprising nonbenzenoid moieties. RSC advances, 11(38), pp. 23437-23441. Royal Society of Chemistry 10.1039/D1RA03253D
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21_Urgel_RSC_Advances_On-surface_synthesis_of_p-conjugated_ladder-type_polymers_comprising_nonbenzenoid_moieties.pdf - Published Version Available under License Creative Commons: Attribution-Noncommercial (CC-BY-NC). Download (690kB) | Preview |
On-surface synthesis provides a powerful approach toward the atomically precise fabrication of π-conjugated ladder polymers (CLPs). We report herein the surface-assisted synthesis of nonbenzenoid CLPs from cyclopenta-annulated anthracene monomers on Au(111) under ultrahigh vacuum conditions. Successive thermal annealing steps reveal the dehalogenative homocoupling to yield an intermediate 1D polymer and the subsequent cyclodehydrogenation to form the fully conjugated ladder polymer. Notably, neighbouring monomers may fuse in two different ways, resulting in six- and five-membered rings, respectively. The structure and electronic properties of the reaction products have been investigated via low-temperature scanning tunneling microscopy and spectroscopy, complemented by density-functional theory calculations. Our results provide perspectives for the on-surface synthesis of nonbenzenoid CLPs with the potential to be used for organic electronic devices.
Item Type: |
Journal Article (Original Article) |
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Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Fasel, Roman |
Subjects: |
500 Science > 530 Physics 500 Science > 540 Chemistry |
ISSN: |
2046-2069 |
Publisher: |
Royal Society of Chemistry |
Language: |
English |
Submitter: |
Roman Fasel |
Date Deposited: |
17 Feb 2022 12:16 |
Last Modified: |
05 Dec 2022 16:05 |
Publisher DOI: |
10.1039/D1RA03253D |
PubMed ID: |
34276968 |
BORIS DOI: |
10.48350/164873 |
URI: |
https://boris.unibe.ch/id/eprint/164873 |
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