Closing the Nanographene Gap: Surface-Assisted Synthesis of Peripentacene from 6,6'-Bipentacene Precursors
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 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.
- Authors:
-
- 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
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- 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 Institutes of Health (NIH)
- OSTI Identifier:
- 1461099
- Grant/Contract Number:
- AC02-05CH11231; SC0010409; DMR‐1206512; SRR023679A; P2ELP2‐151852
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition); Journal Volume: 54; Journal Issue: 50; Related Information: © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 77 NANOSCIENCE AND NANOTECHNOLOGY; arenes; graphene; non-contact AFM; periacene; surface chemistry
Citation Formats
Rogers, Cameron, Chen, Chen, Pedramrazi, Zahra, Omrani, Arash A., Tsai, Hsin-Zon, Jung, Han Sae, Lin, Song, Crommie, Michael F., and Fischer, Felix R. Closing the Nanographene Gap: Surface-Assisted Synthesis of Peripentacene from 6,6'-Bipentacene Precursors. United States: N. p., 2015.
Web. doi:10.1002/anie.201507104.
Rogers, Cameron, Chen, Chen, Pedramrazi, Zahra, Omrani, Arash A., Tsai, Hsin-Zon, Jung, Han Sae, Lin, Song, Crommie, Michael F., & Fischer, Felix R. Closing the Nanographene Gap: Surface-Assisted Synthesis of Peripentacene from 6,6'-Bipentacene Precursors. United States. doi:10.1002/anie.201507104.
Rogers, Cameron, Chen, Chen, Pedramrazi, Zahra, Omrani, Arash A., Tsai, Hsin-Zon, Jung, Han Sae, Lin, Song, Crommie, Michael F., and Fischer, Felix R. Tue .
"Closing the Nanographene Gap: Surface-Assisted Synthesis of Peripentacene from 6,6'-Bipentacene Precursors". United States. doi:10.1002/anie.201507104. https://www.osti.gov/servlets/purl/1461099.
@article{osti_1461099,
title = {Closing the Nanographene Gap: Surface-Assisted Synthesis of Peripentacene from 6,6'-Bipentacene Precursors},
author = {Rogers, Cameron and Chen, Chen and Pedramrazi, Zahra and Omrani, Arash A. and Tsai, Hsin-Zon and Jung, Han Sae and Lin, Song and Crommie, Michael F. and Fischer, Felix R.},
abstractNote = {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.},
doi = {10.1002/anie.201507104},
journal = {Angewandte Chemie (International Edition)},
number = 50,
volume = 54,
place = {United States},
year = {2015},
month = {10}
}
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