Building Pentagons into Graphenic Structures by On-Surface Polymerization and Aromatic Cyclodehydrogenation of Phenyl-Substituted Polycyclic Aromatic Hydrocarbons

Liu, Jia; Dienel, Thomas; Liu, Junzhi; Groening, Oliver; Cai, Jinming; Feng, Xinliang; Müllen, Klaus; Ruffieux, Pascal; Fasel, Roman (2016). Building Pentagons into Graphenic Structures by On-Surface Polymerization and Aromatic Cyclodehydrogenation of Phenyl-Substituted Polycyclic Aromatic Hydrocarbons. Journal of physical chemistry. C, 120(31), pp. 17588-17593. American Chemical Society 10.1021/acs.jpcc.6b05495

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Five-membered carbon rings play a crucial role in determining the geometric structures and electronic properties of carbon-based materials. However, incorporating five-membered rings into low-dimensional carbon nanomaterials with atomic precision is still a challenge. Here, we report on the on-surface synthesis of a one-dimensional conjugated polymer comprising fluoranthene subunits obtained by the surface-assisted aromatic cyclodehydrogenation of 1-phenylnaphthalene moieties within the precursor monomers. By using scanning tunneling microscopy (STM), we investigate the formation of the polymer by thermally induced dehalogenative aryl–aryl coupling and subsequent aromatic cyclodehydrogenation on a Au(111) substrate. The formed five-membered carbon rings are directly observed with atomic resolution by noncontact atomic force microscopy (nc-AFM). Our results show that carefully designed phenyl-substituted polycyclic aromatic hydrocarbons can be used for the rational fabrication of five-membered rings in the bottom-up synthesis of carbon-based nanomaterials and thus add a further tool to the emerging field of on-surface synthesis.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Fasel, Roman

Subjects:

500 Science > 570 Life sciences; biology
500 Science > 540 Chemistry
500 Science > 530 Physics

ISSN:

1932-7447

Publisher:

American Chemical Society

Language:

English

Submitter:

Roman Fasel

Date Deposited:

05 Jan 2017 14:33

Last Modified:

05 Jan 2017 14:33

Publisher DOI:

10.1021/acs.jpcc.6b05495

BORIS DOI:

10.7892/boris.90589

URI:

https://boris.unibe.ch/id/eprint/90589

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