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On-Surface Synthesis of Ethynylene-Bridged Anthracene Polymers
IMDEA Nanociencia, Spain.
Palacky Univ Olomouc, Czech Republic; Czech Acad Sci, Czech Republic.
IMDEA Nanociencia, Spain.
IMDEA Nanociencia, Spain.
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2019 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 20, p. 6559-6563Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2019. Vol. 58, no 20, p. 6559-6563
Keywords [en]
acenes; low-band-gap semiconductors; polymers; scanning probe microscopy; surface chemistry
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:liu:diva-158817DOI: 10.1002/anie.201814154ISI: 000471977400012PubMedID: 30761719OAI: oai:DiVA.org:liu-158817DiVA, id: diva2:1337692
Note

Funding Agencies|Comunidad de Madrid [Y2018/NMT-4783, S2013/MIT-3007, S2018/NMT]; European Research Council [ERC-320441-Chirallcarbon, ERC-766555-ELECNANO]; Spanish Ramon y Cajal programme [RYC-2012-11133]; MINECO of Spain [FIS 2015-67287-P, CTQ2017-83531-R, CTQ2016-81911-REDT]; Severo Ochoa Programme for Centers of Excellence in RD (MINECO) [SEV-2016-0686]; Praemium Academie of the Academy of Science of the Czech Republic [MEYS LM2015087, GACR 18-09914S]; Operational Programme Research, Development, and Education - European Structural and Investment Funds; Czech Ministry of Education, Youth, and Sports [CZ.02.1.01/0.0/0.0/16019/0000754]; Czech Science Foundation [19-27454X]; Swedish Research Council [642-2013-2080]; Swedish Strategic Research Area in Materials Science on Functional Materials at Linkoping University (Faculty Grant SFO-Mat-LiU) [2009 00971]

Available from: 2019-07-16 Created: 2019-07-16 Last updated: 2019-11-08

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