On-Surface Synthesis of Ethynylene-Bridged Anthracene Polymers
Engineering low-band-gap p-conjugated polymers is a growing area in basic and applied research. The main synthetic challenge lies in the solubility of the starting materials, which precludes advancements in the field. Here, we report an on-surface synthesis protocol to overcome such difficulties and...
| Authors: | , , , , , , , , , , , , , |
|---|---|
| Format: | article |
| Publication Date: | 2019 |
| Country: | España |
| Institution: | Universidad Complutense de Madrid (UCM) |
| Repository: | Docta Complutense |
| Language: | English |
| OAI Identifier: | oai:docta.ucm.es:20.500.14352/13868 |
| Online Access: | https://hdl.handle.net/20.500.14352/13868 |
| Access Level: | Open access |
| Keyword: | 547 Acenes low-band-gap semiconductors polymers scanning probe microscopy surface chemistry Química orgánica (Química) 2306 Química Orgánica |
| Summary: | Engineering low-band-gap p-conjugated polymers is a growing area in basic and applied research. The main synthetic challenge lies in the solubility of the starting materials, which precludes advancements in the field. Here, we report an on-surface synthesis protocol to overcome such difficulties and produce poly(p-anthracene ethynylene) molecular wires on Au(111). To this aim, a quinoid anthracene precursor with =CBr2 moieties is deposited and annealed to 400 K, resulting in anthracene-based polymers. High-resolution nc-AFM measurements confirm the nature of the ethynylene-bridge bond between the anthracene moieties. Theoretical simulations illustrate the mechanism of the chemical reaction, highlighting three major steps: dehalogenation, diffusion of surface-stabilized carbenes, and homocoupling, which enables the formation of an ethynylene bridge. Our results introduce a novel chemical protocol to design p-conjugated polymers based on oligoacene precursors and pave new avenues for advancing the emerging field of on-surface synthesis. |
|---|