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Angew Chem Int Ed Engl. 2015 Dec 7;54(50):15143-6. doi: 10.1002/anie.201507104. Epub 2015 Oct 20.

Closing the Nanographene Gap: Surface-Assisted Synthesis of Peripentacene from 6,6'-Bipentacene Precursors.

Author information

1
Department of Chemistry, University of California Berkeley, 699 Tan Hall, Berkeley, CA 94720 (USA).
2
Department of Physics, University of California Berkeley, 345 Birge Hall, Berkeley, CA 94720 (USA).
3
Chemical Science Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA).
4
Department of Physics, University of California Berkeley, 345 Birge Hall, Berkeley, CA 94720 (USA). crommie@berkeley.edu.
5
Materials Science Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA). crommie@berkeley.edu.
6
Kavli Energy NanoSciences Institute at the University of California Berkeley and the Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA). crommie@berkeley.edu.
7
Department of Chemistry, University of California Berkeley, 699 Tan Hall, Berkeley, CA 94720 (USA). ffischer@berkeley.edu.
8
Materials Science Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA). ffischer@berkeley.edu.
9
Kavli Energy NanoSciences Institute at the University of California Berkeley and the Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA). ffischer@berkeley.edu.

Abstract

The thermally induced cyclodehydrogenation reaction of 6,6'-bipentacene precursors on Au(111) yields peripentacene stabilized by surface interactions with the underlying metallic substrate. STM and atomic-resolution non-contact AFM imaging reveal rectangular flakes of nanographene featuring parallel pairs of zig-zag and armchair edges resulting from the lateral fusion of two pentacene subunits. The synthesis of a novel molecular precursor 6,6'-bipentacene, itself a synthetic target of interest for optical and electronic applications, is also reported. The scalable synthetic strategy promises to afford access to a structurally diverse class of extended periacenes and related polycyclic aromatic hydrocarbons as advanced materials for electronic, spintronic, optical, and magnetic devices.

KEYWORDS:

arenes; graphene; non-contact AFM; periacene; surface chemistry

PMID:
26482225
DOI:
10.1002/anie.201507104
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