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Title: Lateral Standing of the Pentacene Derivative 5,6,7-Trithiapentacene-13-one on Gold: A Combined STM, DFT, and NC-AFM Study

In this paper, high resolution scanning tunneling microscopy investigation of the pentacene derivative, 5,6,7-trithiapentacene-13-one (TTPO), on close-packed gold surfaces reveals nanoscale structures ranging from molecular chains at low coverage to highly ordered self-assembled molecular monolayers. Robust, thermally stable, and highly inert to photo-oxidation, TTPO is a promising organic semiconductor with potential applications in high-temperature photovoltaic devices. When adsorbed on a gold electrode, experiment and first-principle computation reveal a novel 3-D angular assembly of the TTPO molecules, with the long axis of the molecule parallel to the gold surface, distinctive from previously observed pentacene and pentacene derivative assemblies. Structures assembled are angularly dependent on TTPO molecular interactions while commensurate with the underlying gold substrate, allowing for potential tailoring of π-molecular orbital overlap through tilt-angle control. Finally, rigorous noncontact atomic force microscopy analysis was used to experimentally determine the molecular tilt of the molecule at 5 K, consistent with the calculated and observed structures at room temperature.
Authors:
ORCiD logo [1] ;  [1] ;  [2] ;  [1] ;  [1] ;  [3] ;  [4] ;  [5]
  1. Univ. of New Hampshire, Durham, NH (United States). Dept. of Physics
  2. Univ. of New Hampshire, Durham, NH (United States). Dept. of Chemistry
  3. Brookhaven National Lab. (BNL), Upton, NY (United States). Center for Functional Nanomaterials
  4. Univ. of New Hampshire, Durham, NH (United States). Dept. of Chemistry. Materials Science Program
  5. Univ. of New Hampshire, Durham, NH (United States). Dept. of Physics. Materials Science Program
Publication Date:
Report Number(s):
BNL-207939-2018-JAAM
Journal ID: ISSN 1932-7447
Grant/Contract Number:
SC0012704; EEC-0425826; DMR-1006863; EPS-0701730; PHY-1229408
Type:
Accepted Manuscript
Journal Name:
Journal of Physical Chemistry. C
Additional Journal Information:
Journal Volume: 122; Journal Issue: 22; Journal ID: ISSN 1932-7447
Publisher:
American Chemical Society
Research Org:
Brookhaven National Lab. (BNL), Upton, NY (United States); Univ. of New Hampshire, Durham, NH (United States)
Sponsoring Org:
USDOE Office of Science (SC); National Science Foundation (NSF)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
OSTI Identifier:
1466642

Larson, Amanda M., van Baren, Jeremiah, Kintigh, Jeremy, Wang, Jun, Tang, Jian-Ming, Zahl, Percy, Miller, Glen P., and Pohl, Karsten. Lateral Standing of the Pentacene Derivative 5,6,7-Trithiapentacene-13-one on Gold: A Combined STM, DFT, and NC-AFM Study. United States: N. p., Web. doi:10.1021/acs.jpcc.8b03633.
Larson, Amanda M., van Baren, Jeremiah, Kintigh, Jeremy, Wang, Jun, Tang, Jian-Ming, Zahl, Percy, Miller, Glen P., & Pohl, Karsten. Lateral Standing of the Pentacene Derivative 5,6,7-Trithiapentacene-13-one on Gold: A Combined STM, DFT, and NC-AFM Study. United States. doi:10.1021/acs.jpcc.8b03633.
Larson, Amanda M., van Baren, Jeremiah, Kintigh, Jeremy, Wang, Jun, Tang, Jian-Ming, Zahl, Percy, Miller, Glen P., and Pohl, Karsten. 2018. "Lateral Standing of the Pentacene Derivative 5,6,7-Trithiapentacene-13-one on Gold: A Combined STM, DFT, and NC-AFM Study". United States. doi:10.1021/acs.jpcc.8b03633.
@article{osti_1466642,
title = {Lateral Standing of the Pentacene Derivative 5,6,7-Trithiapentacene-13-one on Gold: A Combined STM, DFT, and NC-AFM Study},
author = {Larson, Amanda M. and van Baren, Jeremiah and Kintigh, Jeremy and Wang, Jun and Tang, Jian-Ming and Zahl, Percy and Miller, Glen P. and Pohl, Karsten},
abstractNote = {In this paper, high resolution scanning tunneling microscopy investigation of the pentacene derivative, 5,6,7-trithiapentacene-13-one (TTPO), on close-packed gold surfaces reveals nanoscale structures ranging from molecular chains at low coverage to highly ordered self-assembled molecular monolayers. Robust, thermally stable, and highly inert to photo-oxidation, TTPO is a promising organic semiconductor with potential applications in high-temperature photovoltaic devices. When adsorbed on a gold electrode, experiment and first-principle computation reveal a novel 3-D angular assembly of the TTPO molecules, with the long axis of the molecule parallel to the gold surface, distinctive from previously observed pentacene and pentacene derivative assemblies. Structures assembled are angularly dependent on TTPO molecular interactions while commensurate with the underlying gold substrate, allowing for potential tailoring of π-molecular orbital overlap through tilt-angle control. Finally, rigorous noncontact atomic force microscopy analysis was used to experimentally determine the molecular tilt of the molecule at 5 K, consistent with the calculated and observed structures at room temperature.},
doi = {10.1021/acs.jpcc.8b03633},
journal = {Journal of Physical Chemistry. C},
number = 22,
volume = 122,
place = {United States},
year = {2018},
month = {5}
}