Large-Cavity Coronoids with Different Inner and Outer Edge Structures

Di Giovannantonio, Marco; Yao, Xuelin; Eimre, Kristjan; Urgel, José I.; Ruffieux, Pascal; Pignedoli, Carlo A.; Müllen, Klaus; Fasel, Roman; Narita, Akimitsu (2020). Large-Cavity Coronoids with Different Inner and Outer Edge Structures. Journal of the American Chemical Society, 142(28), pp. 12046-12050. American Chemical Society 10.1021/jacs.0c05268

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Coronoids, polycyclic aromatic hydrocarbons with geometrically defined cavities, are promising model structures of porous graphene. Here, we report the on-surface synthesis of C168 and C140 coronoids, referred to as [6]- and [5]coronoid, respectively, using 5,9-dibromo-14-phenylbenzo[m]tetraphene as the precursor. These coronoids entail large cavities (>1 nm) with inner zigzag edges, distinct from their outer armchair edges. While [6]coronoid is planar, [5]coronoid is not. Low-temperature scanning tunneling microscopy/spectroscopy and noncontact atomic force microscopy unveil structural and electronic properties in accordance with those obtained from density functional theory calculations. Detailed analysis of ring current effects identifies the rings with the highest aromaticity of these coronoids, whose pattern matches their Clar structure. The pores of the obtained coronoids offer intriguing possibilities of further functionalization toward advanced host-guest applications.

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:

0002-7863

Publisher:

American Chemical Society

Language:

English

Submitter:

Roman Fasel

Date Deposited:

03 Sep 2020 16:16

Last Modified:

03 Sep 2020 16:16

Publisher DOI:

10.1021/jacs.0c05268

BORIS DOI:

10.7892/boris.146336

URI:

https://boris.unibe.ch/id/eprint/146336

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