On-Surface Synthesis of Ethynylene-Bridged Anthracene Polymers
Engineering low-band-gap p-conjugated polymersis a growing area in basic and applied research. The mainsynthetic challenge lies in the solubility of the starting materials,which precludes advancements in the field. Here, we report anon-surface synthesis protocol to overcome such difficulties andprod...
| Autores: | , , , , , , , , , , , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2019 |
| País: | España |
| Institución: | Universidad Autónoma de Madrid |
| Repositorio: | Biblos-e Archivo. Repositorio Institucional de la UAM |
| Idioma: | inglés |
| OAI Identifier: | oai:repositorio.uam.es:10486/713843 |
| Acceso en línea: | http://hdl.handle.net/10486/713843 https://dx.doi.org/10.1002/anie.201814154 |
| Access Level: | acceso abierto |
| Palabra clave: | Acenes low-band-gap semiconductors polymers scanning probe microscopy surface chemistry Física |
| Sumario: | Engineering low-band-gap p-conjugated polymersis a growing area in basic and applied research. The mainsynthetic challenge lies in the solubility of the starting materials,which precludes advancements in the field. Here, we report anon-surface synthesis protocol to overcome such difficulties andproduce poly(p-anthracene ethynylene) molecular wires onAu(111). To this aim, a quinoid anthracene precursor with=CBr2 moieties is deposited and annealed to 400 K, resulting inanthracene-based polymers. High-resolution nc-AFM meas-urements confirm the nature of the ethynylene-bridge bondbetween the anthracene moieties. Theoretical simulationsillustrate the mechanism of the chemical reaction, highlightingthree major steps: dehalogenation, diffusion of surface-stabi-lized carbenes, and homocoupling, which enables the forma-tion of an ethynylene bridge. Our results introduce a novelchemical protocol to design p-conjugated polymers based onoligoacene precursors and pave new avenues for advancing theemerging field of on-surface synthesis |
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