On‐Surface Synthesis of Cumulene‐Containing Polymers via Two‐Step Dehalogenative Homocoupling of Dibromomethylene‐Functionalized Tribenzoazulene

Urgel, José I.; Di Giovannantonio, Marco; Eimre, Kristjan; Lohr, Thorsten G.; Liu, Junzhi; Mishra, Shantanu; Sun, Qiang; Kinikar, Amogh; Widmer, Roland; Stolz, Samuel; Bommert, Max; Berger, Reinhard; Ruffieux, Pascal; Pignedoli, Carlo A.; Müllen, Klaus; Feng, Xinliang; Fasel, Roman (2020). On‐Surface Synthesis of Cumulene‐Containing Polymers via Two‐Step Dehalogenative Homocoupling of Dibromomethylene‐Functionalized Tribenzoazulene. Angewandte Chemie (International ed.), 59(32), pp. 13281-13287. Wiley-VCH 10.1002/anie.202001939

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Cumulene compounds are notoriously difficult to prepare and study due to dramatically increasing reactivity with increasing number of consecutive double bonds. In this respect, the emerging field of on‐surface synthesis provides exceptional opportunities because it relies on reactions on clean metal substrates under well‐controlled ultrahigh vacuum conditions. Here we report the on‐surface synthesis of a polymer linked by cumulene‐like bonds on a Au(111) surface via sequential thermally activated dehalogenative C-C coupling of a tribenzo‐azulene precursor equipped with two dibromomethylenes. The structure and electronic properties of the resulting polymer with cumulene‐like pentagon‐pentagon and heptagon‐heptagon connections have been investigated by means of scanning probe microscopy and spectroscopy methods and X‐ray photoelectron spectroscopy, complemented by density functional theory calculations. Our results provide perspectives for the on‐surface synthesis of compounds containing cumulene‐like bonds, as well as protocols relevant to the stepwise fabrication of carbon‐carbon bonds on surfaces.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Fasel, Roman

Subjects:

500 Science > 530 Physics
500 Science > 540 Chemistry

ISSN:

1433-7851

Publisher:

Wiley-VCH

Language:

English

Submitter:

Roman Fasel

Date Deposited:

03 Sep 2020 15:23

Last Modified:

03 Sep 2020 15:23

Publisher DOI:

10.1002/anie.202001939

BORIS DOI:

10.7892/boris.146330

URI:

https://boris.unibe.ch/id/eprint/146330

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