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Title: Understanding Electron Transport in Disk-Shaped Triphenylene-Tris(naphthaleneimidazole)s through Structural Modification and Theoretical Investigation

Abstract

We report that disk-shaped molecules with large aromatic π-surfaces are a class of organic semiconductors in which the charge-carrier transport properties could be greatly facilitated by preferred intermolecular stacking of the π-surfaces. The optical and electronic properties are not only determined by the core aromatic structure of these disk-shaped molecules but are also strongly dependent on the side chains, which directly impact the molecular self-assembly behavior in condensed phases. Triphenylene-tris(naphthaleneimidazole) (TP-TNI) is a recently reported n-type semiconductor featuring a large π-core and branched side chains, with an electron-transporting mobility reaching 10 -4 cm 2 V -1 s -1. To further improve material performance, a detailed study is needed to understand the dependence of carrier transport properties on both the core electronic structure and side chain. Here, we present the detailed synthesis and characterization of a TP-TNI derivative bearing linear side chains, which has demonstrated a field-effect electron-transport mobility of up to 1.3 × 10 -3 cm 2 V -1 s -1. The more than 1 order improvement in electron-transport properties over the branched side chain homologue can be correlated to ordered twisted packing in the thin film, as revealed by in situ variable temperature grazing incidence wide-angle X-ray scattering studies.more » In conclusion, in-depth theoretical understanding of the frontier orbitals, reorganization energies, and charge-transfer integrals of TP-TNI molecules has provided further insight into the relationship between the molecular stacking geometry and charge-transport properties.« less

Authors:
 [1];  [2];  [3];  [4]; ORCiD logo [5];  [3]; ORCiD logo [4]
  1. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Nanjing Tech Univ. (China)
  2. Stanford Univ., Palo Alto, CA (United States)
  3. Universidad de Jaén, Campus Las Lagunillas (Spain)
  4. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
  5. Florida State Univ., Tallahassee, FL (United States)
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)
OSTI Identifier:
1530289
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
ACS Applied Materials and Interfaces
Additional Journal Information:
Journal Volume: 9; Journal Issue: 23; Journal ID: ISSN 1944-8244
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE; charge transport; columnar stacking; disk-shaped molecules; n-type; organic semiconductor

Citation Formats

Zhang, Yue, Hanifi, David A., Fernández-Liencres, M. Paz, Klivansky, Liana M., Ma, Biwu, Navarro, Amparo, and Liu, Yi. Understanding Electron Transport in Disk-Shaped Triphenylene-Tris(naphthaleneimidazole)s through Structural Modification and Theoretical Investigation. United States: N. p., 2017. Web. doi:10.1021/acsami.7b03795.
Zhang, Yue, Hanifi, David A., Fernández-Liencres, M. Paz, Klivansky, Liana M., Ma, Biwu, Navarro, Amparo, & Liu, Yi. Understanding Electron Transport in Disk-Shaped Triphenylene-Tris(naphthaleneimidazole)s through Structural Modification and Theoretical Investigation. United States. doi:10.1021/acsami.7b03795.
Zhang, Yue, Hanifi, David A., Fernández-Liencres, M. Paz, Klivansky, Liana M., Ma, Biwu, Navarro, Amparo, and Liu, Yi. Fri . "Understanding Electron Transport in Disk-Shaped Triphenylene-Tris(naphthaleneimidazole)s through Structural Modification and Theoretical Investigation". United States. doi:10.1021/acsami.7b03795. https://www.osti.gov/servlets/purl/1530289.
@article{osti_1530289,
title = {Understanding Electron Transport in Disk-Shaped Triphenylene-Tris(naphthaleneimidazole)s through Structural Modification and Theoretical Investigation},
author = {Zhang, Yue and Hanifi, David A. and Fernández-Liencres, M. Paz and Klivansky, Liana M. and Ma, Biwu and Navarro, Amparo and Liu, Yi},
abstractNote = {We report that disk-shaped molecules with large aromatic π-surfaces are a class of organic semiconductors in which the charge-carrier transport properties could be greatly facilitated by preferred intermolecular stacking of the π-surfaces. The optical and electronic properties are not only determined by the core aromatic structure of these disk-shaped molecules but are also strongly dependent on the side chains, which directly impact the molecular self-assembly behavior in condensed phases. Triphenylene-tris(naphthaleneimidazole) (TP-TNI) is a recently reported n-type semiconductor featuring a large π-core and branched side chains, with an electron-transporting mobility reaching 10-4 cm2 V-1 s-1. To further improve material performance, a detailed study is needed to understand the dependence of carrier transport properties on both the core electronic structure and side chain. Here, we present the detailed synthesis and characterization of a TP-TNI derivative bearing linear side chains, which has demonstrated a field-effect electron-transport mobility of up to 1.3 × 10-3 cm2 V-1 s-1. The more than 1 order improvement in electron-transport properties over the branched side chain homologue can be correlated to ordered twisted packing in the thin film, as revealed by in situ variable temperature grazing incidence wide-angle X-ray scattering studies. In conclusion, in-depth theoretical understanding of the frontier orbitals, reorganization energies, and charge-transfer integrals of TP-TNI molecules has provided further insight into the relationship between the molecular stacking geometry and charge-transport properties.},
doi = {10.1021/acsami.7b03795},
journal = {ACS Applied Materials and Interfaces},
number = 23,
volume = 9,
place = {United States},
year = {2017},
month = {6}
}

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