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Title: 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:
 [1];  [2];  [2];  [2];  [2];  [2];  [3];  [4];  [5]
  1. Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
  2. Univ. of California, Berkeley, CA (United States). Dept. of Physics
  3. Univ. of California, Berkeley, CA (United States). Dept. of Chemistry; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Chemical Science Division
  4. 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
  5. 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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Cited by: 41 works
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