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Title: Tethered tertiary amines as solid-state n-type dopants for solution-processable organic semiconductors

Journal Article · · Chemical Science
DOI: https://doi.org/10.1039/c5sc04217h · OSTI ID:1377413
 [1];  [2];  [3];  [4];  [2];  [2];  [5];  [6];  [7];  [8];  [6];  [7];  [5]
  1. Univ. of California, Berkeley, CA (United States). Dept. of Chemical and Biomolecular Engineering; Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
  2. Univ. of California, Santa Barbara, CA (United States). Dept. of Chemistry and Biochemistry
  3. Univ. of California, Santa Barbara, CA (United States). Dept. of Chemical Engineering
  4. Univ. of California, Santa Barbara, CA (United States). Materials Dept.
  5. Univ. of California, Santa Barbara, CA (United States). Dept. of Chemical Engineering; Univ. of California, Santa Barbara, CA (United States). Materials Dept.
  6. Univ. of California, Santa Barbara, CA (United States). Materials Dept
  7. Univ. of California, Santa Barbara, CA (United States). Dept. of Chemistry and Biochemistry; Univ. of California, Santa Barbara, CA (United States). Materials Dept.
  8. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
+ Show Author Affiliations

A scarcity of stable n-type doping strategies compatible with facile processing has been a major impediment to the advancement of organic electronic devices. Localizing dopants near the cores of conductive molecules can lead to improved efficacy of doping. We and others recently showed the effectiveness of tethering dopants covalently to an electron-deficient aromatic molecule using trimethylammonium functionalization with hydroxide counterions linked to a perylene diimide core by alkyl spacers. In this work, we demonstrate that, contrary to previous hypotheses, the main driver responsible for the highly effective doping observed in thin films is the formation of tethered tertiary amine moieties during thin film processing. Furthermore, we demonstrate that tethered tertiary amine groups are powerful and general n-doping motifs for the successful generation of free electron carriers in the solid-state, not only when coupled to the perylene diimide molecular core, but also when linked with other small molecule systems including naphthalene diimide, diketopyrrolopyrrole, and fullerene derivatives. Our findings help expand a promising molecular design strategy for future enhancements of n-type organic electronic materials.

Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); National Science Foundation (NSF)
Grant/Contract Number:
AC02-05CH11231
OSTI ID:
1377413
Journal Information:
Chemical Science, Journal Name: Chemical Science Journal Issue: 3 Vol. 7; ISSN 2041-6520; ISSN CSHCBM
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

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Cited By (12)

Progress and Perspective: Soft Thermoelectric Materials for Wearable and Internet‐of‐Things Applications journal February 2019
Molecular Level Insight into Enhanced n‐Type Transport in Solution‐Printed Hybrid Thermoelectrics journal February 2019
Air‐Stable n‐Type Thermoelectric Materials Enabled by Organic Diradicaloids journal March 2019
Air-Stable n-Type Thermoelectric Materials Enabled by Organic Diradicaloids journal March 2019
Organic thermoelectric materials for energy harvesting and temperature control journal August 2016
Anion-induced N-doping of naphthalenediimide polymer semiconductor in organic thin-film transistors journal April 2018
High-performance n-type thermoelectric composites of acridones with tethered tertiary amines and carbon nanotubes journal January 2018
Self-doping small molecular conjugated electrolytes enabled by n-type side chains for highly efficient non-fullerene polymer solar cells journal January 2018
Ruthenium pentamethylcyclopentadienyl mesitylene dimer: a sublimable n-dopant and electron buffer layer for efficient n–i–p perovskite solar cells journal January 2019
Controlling intermolecular redox-doping of naphthalene diimides journal January 2019
Sulfur-fused perylene diimide electron transport layers allow >400 h operational lifetime of methylammonium lead iodide photovoltaics journal January 2019
Water/Alcohol Soluble Thickness-Insensitive Hyperbranched Perylene Diimide Electron Transport Layer Improving the Efficiency of Organic Solar Cells journal April 2019

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