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

Cameron Rogers; Chen Chen; Zahra Pedramrazi; Arash A Omrani; Hsin-Zon Tsai; Han Sae Jung; Song Lin; Michael F Crommie; Felix R Fischer

doi:10.1002/anie.201507104

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

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

Authors

Cameron Rogers¹, Chen Chen², Zahra Pedramrazi², Arash A Omrani², Hsin-Zon Tsai², Han Sae Jung², Song Lin^{1

3}, Michael F Crommie^{4

5

6}, Felix R Fischer^{7

8

9}

Affiliations

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). [email protected].
⁵ Materials Science Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA). [email protected].
⁶ Kavli Energy NanoSciences Institute at the University of California Berkeley and the Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA). [email protected].
⁷ Department of Chemistry, University of California Berkeley, 699 Tan Hall, Berkeley, CA 94720 (USA). [email protected].
⁸ Materials Science Division, Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA). [email protected].
⁹ Kavli Energy NanoSciences Institute at the University of California Berkeley and the Lawrence Berkeley National Laboratory, Berkeley, CA 94720 (USA). [email protected].

PMID: 26482225
DOI: 10.1002/anie.201507104

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.