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Direct Formation of C-C Double-Bonded Structural Motifs by On-Surface Dehalogenative Homocoupling of gem-Dibromomethyl Molecules
Tongji Univ, Peoples R China.
Tongji Univ, Peoples R China.
Natl Ctr Nanosci and Technol, Peoples R China.
Tongji Univ, Peoples R China.
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2018 (English)In: ACS Nano, ISSN 1936-0851, E-ISSN 1936-086X, Vol. 12, no 8, p. 7959-7966Article in journal (Refereed) Published
Abstract [en]

Conductive polymers are of great importance in a variety of chemistry-related disciplines and applications. The recently developed bottom-up on-surface synthesis strategy provides us with opportunities for the fabrication of various nanostructures in a flexible and facile manner, which could be investigated by high-resolution microscopic techniques in real space. Herein, we designed and synthesized molecular precursors functionalized with benzal gem-dibromomethyl groups. A combination of scanning tunneling microscopy, noncontact atomic force microscopy, high-resolution synchrotron radiation photoemission spectroscopy, and density functional theory calculations demonstrated that it is feasible to achieve the direct formation of C-C double-bonded structural motifs via on-surface dehalogenative homocoupling reactions on the Au(111) surface. Correspondingly, we convert the sp(3)-hybridized state to an sp(2)-hybridized state of carbon atoms, i.e., from an alkyl group to an alkenyl one. Moreover, by such a bottom-up strategy, we have successfully fabricated poly(phenylenevinylene) chains on the surface, which is anticipated to inspire further studies toward understanding the nature of conductive polymers at the atomic scale.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2018. Vol. 12, no 8, p. 7959-7966
Keywords [en]
dehalogenative homocoupling; gem-dibromomethyl; scanning tunneling microscopy; noncontact atomic force microscopy; surface chemistry
National Category
Materials Chemistry
Identifiers
URN: urn:nbn:se:liu:diva-151513DOI: 10.1021/acsnano.8b02459ISI: 000443525600047PubMedID: 30016072OAI: oai:DiVA.org:liu-151513DiVA, id: diva2:1250605
Note

Funding Agencies|National Natural Science Foundation of China [21473123, 21622307, 21790351, 51403157, 21603045, 21425310, 91427301]; Fundamental Research Funds for the Central Universities of China [2018XKJC-009]; International Cooperation Training Project Funding for Postgraduate of Tonggji University [2018XKJC-009]; Alexander von Humboldt Foundation

Available from: 2018-09-24 Created: 2018-09-24 Last updated: 2018-09-24

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