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

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

doi:10.1002/anie.201507104

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

Journal Article · 19 October 2015 · Angewandte Chemie (International Edition)

DOI: https://doi.org/10.1002/anie.201507104 · OSTI ID:1461099

Rogers, Cameron ^[1]; Chen, Chen ^[2]; Pedramrazi, Zahra ^[2]; Omrani, Arash A. ^[2]; Tsai, Hsin-Zon ^[2]; Jung, Han Sae ^[2]; Lin, Song ^[3]; Crommie, Michael F. ^[4]; Fischer, Felix R. ^[5]

Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
Univ. of California, Berkeley, CA (United States). Dept. of Physics
Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Science Division
Univ. of California, Berkeley, CA (United States). Kavli Energy NanoScience Inst. and Dept. of Physics; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Materials Science Division
Univ. of California, Berkeley, CA (United States). Dept. of Chemistry, Kavli Energy NanoScience Inst. and Dept. of Physics; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Materials Science Division

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 here. 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.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); US Department of the Navy, Office of Naval Research (ONR); National Science Foundation (NSF); Swiss National Science Foundation (SNSF); National Inst. of Health (NIH)

Grant/Contract Number:: AC02-05CH11231; SC0010409

OSTI ID:: 1461099

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 50 Vol. 54; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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

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