On-Surface Synthesis of Ethynylene-Bridged Anthracene Polymers
Status PubMed-not-MEDLINE Language English Country Germany Media print-electronic
Document type Journal Article
Grant support
766555
H2020 European Research Council
320441
H2020 European Research Council
PubMed
30761719
PubMed Central
PMC6563096
DOI
10.1002/anie.201814154
Knihovny.cz E-resources
- Keywords
- acenes, low-band-gap semiconductors, polymers, scanning probe microscopy, surface chemistry,
- Publication type
- Journal Article MeSH
Engineering low-band-gap π-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 π-conjugated polymers based on oligoacene precursors and pave new avenues for advancing the emerging field of on-surface synthesis.
Department of Physics Chemistry and Biology IFM Linköping University 58183 Linköping Sweden
IMDEA Nanociencia C Faraday 9 Ciudad Universitaria de Cantoblanco 28049 Madrid Spain
Institute of Physics The Czech Academy of Sciences Cukrovarnická 10 16200 Prague 6 Czech Republic
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