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On-Surface Synthesis of Ethynylene-Bridged Anthracene Polymers

Sanchez-Grande, Ana; de la Torre, Bruno; Santos, Jose; Cirera, Borja; Lauwaet, Koen; Chutora, Taras; Edalatmanesh, Shayan; Mutombo, Pingo; Rosen, Johanna; Zboril, Radek; Miranda, Rodolfo; Bjork, Jonas; Jelinek, Pavel; Martin, Nazario; Ecija, David

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
2019
VL / 58 - BP / 6559 - EP / 6563
abstract
Engineering low-band-gap -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 400K, 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 -conjugated polymers based on oligoacene precursors and pave new avenues for advancing the emerging field of on-surface synthesis.

AccesS level

Green published, Hybrid

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