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Title: Buta-1,3-diyne-Based π-Conjugated Polymers for Organic Transistors and Solar Cells

Abstract

We report the synthesis and characterization of new alkyl-substituted 1,4-di(thiophen-2-yl)buta-1,3-diyne (R-DTB) donor building blocks, based on the -C≡C-C≡C- conjugative pathway, and their incorporation with thienyl-diketopyrrolopyrrole (R'-TDPP) acceptor units into π-conjugated PTDPP-DTB polymers (P1-P4). The solubility of the new polymers strongly depends on the DTB and DPP solubilizing (R and R', respectively) substituents. Thus, solution processable and high molecular weight PDPP-DTB polymers are achieved for P3 (R = n-C12H25, R' = 2- butyloctyl) and P4 (R = 2-ethylhexyl, R' = 2-butyloctyl). Systematic studies of P3 and P4 physicochemical properties are carried using optical spectroscopy, cyclic voltammetry, and thermal analysis, revealing characteristic features of the dialkynyl motif. For the first time, optoelectronic devices (OFETs, OPVs) are fabricated with 1,3-butadiyne containing organic semiconductors. OFET hole mobilities and record OPV power conversion efficiencies for acetylenic organic materials approach 0.1 cm2/(V s) and 4%, respectively, which can be understood from detailed thin-film morphology and microstructural characterization using AFM, TEM, XRD, and GIWAXS methodologies. Importantly, DTB-based polymers (P3 and P4) exhibit, in addition to stabilization of frontier molecular orbitals and to -C≡C-C≡C- relief of steric torsions, discrete morphological pliability through thermal annealing and processing additives. The advantageous materials properties and preliminary device performance reported here demonstratemore » the promise of 1,3-butadiyne-based semiconducting polymers.« less

Authors:
; ORCiD logo; ; ; ; ; ; ; ; ORCiD logo
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1395348
DOE Contract Number:
AC02-06CH11357
Resource Type:
Journal Article
Resource Relation:
Journal Name: Macromolecules; Journal Volume: 50; Journal Issue: 4
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Eckstein, Brian J., Melkonyan, Ferdinand S., Zhou, Nanjia, Manley, Eric F., Smith, Jeremy, Timalsina, Amod, Chang, Robert P. H., Chen, Lin X., Facchetti, Antonio, and Marks, Tobin J.. Buta-1,3-diyne-Based π-Conjugated Polymers for Organic Transistors and Solar Cells. United States: N. p., 2017. Web. doi:10.1021/acs.macromol.6b02702.
Eckstein, Brian J., Melkonyan, Ferdinand S., Zhou, Nanjia, Manley, Eric F., Smith, Jeremy, Timalsina, Amod, Chang, Robert P. H., Chen, Lin X., Facchetti, Antonio, & Marks, Tobin J.. Buta-1,3-diyne-Based π-Conjugated Polymers for Organic Transistors and Solar Cells. United States. doi:10.1021/acs.macromol.6b02702.
Eckstein, Brian J., Melkonyan, Ferdinand S., Zhou, Nanjia, Manley, Eric F., Smith, Jeremy, Timalsina, Amod, Chang, Robert P. H., Chen, Lin X., Facchetti, Antonio, and Marks, Tobin J.. Thu . "Buta-1,3-diyne-Based π-Conjugated Polymers for Organic Transistors and Solar Cells". United States. doi:10.1021/acs.macromol.6b02702.
@article{osti_1395348,
title = {Buta-1,3-diyne-Based π-Conjugated Polymers for Organic Transistors and Solar Cells},
author = {Eckstein, Brian J. and Melkonyan, Ferdinand S. and Zhou, Nanjia and Manley, Eric F. and Smith, Jeremy and Timalsina, Amod and Chang, Robert P. H. and Chen, Lin X. and Facchetti, Antonio and Marks, Tobin J.},
abstractNote = {We report the synthesis and characterization of new alkyl-substituted 1,4-di(thiophen-2-yl)buta-1,3-diyne (R-DTB) donor building blocks, based on the -C≡C-C≡C- conjugative pathway, and their incorporation with thienyl-diketopyrrolopyrrole (R'-TDPP) acceptor units into π-conjugated PTDPP-DTB polymers (P1-P4). The solubility of the new polymers strongly depends on the DTB and DPP solubilizing (R and R', respectively) substituents. Thus, solution processable and high molecular weight PDPP-DTB polymers are achieved for P3 (R = n-C12H25, R' = 2- butyloctyl) and P4 (R = 2-ethylhexyl, R' = 2-butyloctyl). Systematic studies of P3 and P4 physicochemical properties are carried using optical spectroscopy, cyclic voltammetry, and thermal analysis, revealing characteristic features of the dialkynyl motif. For the first time, optoelectronic devices (OFETs, OPVs) are fabricated with 1,3-butadiyne containing organic semiconductors. OFET hole mobilities and record OPV power conversion efficiencies for acetylenic organic materials approach 0.1 cm2/(V s) and 4%, respectively, which can be understood from detailed thin-film morphology and microstructural characterization using AFM, TEM, XRD, and GIWAXS methodologies. Importantly, DTB-based polymers (P3 and P4) exhibit, in addition to stabilization of frontier molecular orbitals and to -C≡C-C≡C- relief of steric torsions, discrete morphological pliability through thermal annealing and processing additives. The advantageous materials properties and preliminary device performance reported here demonstrate the promise of 1,3-butadiyne-based semiconducting polymers.},
doi = {10.1021/acs.macromol.6b02702},
journal = {Macromolecules},
number = 4,
volume = 50,
place = {United States},
year = {Thu Feb 09 00:00:00 EST 2017},
month = {Thu Feb 09 00:00:00 EST 2017}
}