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On-Surface Synthesis of Ethynylene-Bridged Anthracene Polymers

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Sánchez Grande, Ana and De la Torre, Bruno and Santos, José and Cirera, Borja and Lauwaet, Koen and Chutora, Taras and Edalatmanesh, Shayan and Rosen, Johanna and Zboril, Radek and Miranda, Rodolfo and Björk, Jonas and Jelínek, Pavel and Martín, Nazario and Ecija, David (2019) On-Surface Synthesis of Ethynylene-Bridged Anthracene Polymers. Angewandte chemie. International edition, 58 (20). pp. 6559-6563. ISSN 1433-7851

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Official URL: https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.201814154



Abstract

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.


Item Type:Article
Uncontrolled Keywords:Acenes; low-band-gap semiconductors; polymers; scanning probe microscopy; surface chemistry
Subjects:Sciences > Chemistry > Chemistry, Organic
ID Code:58526
Deposited On:14 Jan 2020 12:27
Last Modified:14 Jan 2020 12:53

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