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Title: Kinetically Controlled Formation of Semi-crystalline Conjugated Polymer Nanostructures

Abstract

Conjugated polymer (CP) materials that are considered as an attractive choice for various electronic and optoelectronic applications possess highly heterogeneous complex structures that can span several orders of magnitude in length scale. This is due to the intricate coupling effects of weak secondary interactions and entropic forces that determine molecular organization in bulk polymer materials. Understanding the influence of molecular interactions on the emergence and evolution of nano- and microscale structures is of paramount importance to the guided design and development of condensed CP materials. Such understanding is even more critical for the rational design of hierarchical systems away from equilibrium, where weak molecular interactions can guide the system along competing kinetic pathways toward local energy minima and metastable architectures. In this work, we studied a promising concept for accessing various kinetically stabilized semi-crystalline CP nanostructures that are formed in the process of controlled chain-growth Kumada catalyst-transfer polymerization initiated by a small-molecule catalytic species which can exist in equilibrium between free and aggregated states. Specifically, we chose a small-molecule perylenedicarboximide (PDCI) polymerization catalytic initiator which has a strong tendency toward reversible supramolecular assembly–disassembly that can be controlled by temperature. Addition of a thiophene monomer to a solution of the PDCImore » initiator starts the chain-growth polymerization process, which produces distinct nanoscale semi-crystalline polythiophene structures formed under predominant kinetic control. Furthermore, we demonstrated that, depending on the reaction temperature (which affects the fine balance between the position of PDCI assembly–disassembly equilibrium, rate of polymerization, and solvent–solute interactions for the growing polythiophene chains), a range of kinetically trapped hierarchically organized semi-crystalline CP systems with substantially varying optoelectronic properties could be obtained. In addition to spectroscopic and electron microscopic studies, in order to better reveal the structural aspects of the generated polymer nanoscale systems, we carried out a series of X-ray diffraction and neutron scattering experiments which indicated complex hierarchical organization in these kinetically stabilized CP assembled materials. We expect that this in situ polymerization-based approach can lead to a general way to expand access to various semi-crystalline CP nanostructured materials with broadly tunable electronic and optical properties.« less

Authors:
 [1];  [2];  [1];  [1]; ORCiD logo [3]; ORCiD logo [4]; ORCiD logo [5]
+ Show Author Affiliations
  1. Louisiana State Univ., Baton Rouge, LA (United States)
  2. Northern Illinois Univ., DeKalb, IL (United States)
  3. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
  4. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS)
  5. Louisiana State Univ., Baton Rouge, LA (United States); Northern Illinois Univ., DeKalb, IL (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1777694
Grant/Contract Number:  
AC05-00OR22725; SC0012432; CHE-1726931
Resource Type:
Accepted Manuscript
Journal Name:
Macromolecules
Additional Journal Information:
Journal Volume: 54; Journal Issue: 5; Journal ID: ISSN 0024-9297
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; supramolecular structures and assemblies; polymerization; nanoparticles; chromophores; polymers

Citation Formats

Kei, Peter, Howell, Mitchell T., Chavez, Carlos A., Mai, Joseph C., Do, Changwoo, Hong, Kunlun, and Nesterov, Evgueni E. Kinetically Controlled Formation of Semi-crystalline Conjugated Polymer Nanostructures. United States: N. p., 2021. Web. doi:10.1021/acs.macromol.0c02774.
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Kei, Peter, Howell, Mitchell T., Chavez, Carlos A., Mai, Joseph C., Do, Changwoo, Hong, Kunlun, & Nesterov, Evgueni E. Kinetically Controlled Formation of Semi-crystalline Conjugated Polymer Nanostructures. United States. https://doi.org/10.1021/acs.macromol.0c02774
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Kei, Peter, Howell, Mitchell T., Chavez, Carlos A., Mai, Joseph C., Do, Changwoo, Hong, Kunlun, and Nesterov, Evgueni E. Fri . "Kinetically Controlled Formation of Semi-crystalline Conjugated Polymer Nanostructures". United States. https://doi.org/10.1021/acs.macromol.0c02774. https://www.osti.gov/servlets/purl/1777694.
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@article{osti_1777694,
title = {Kinetically Controlled Formation of Semi-crystalline Conjugated Polymer Nanostructures},
author = {Kei, Peter and Howell, Mitchell T. and Chavez, Carlos A. and Mai, Joseph C. and Do, Changwoo and Hong, Kunlun and Nesterov, Evgueni E.},
abstractNote = {Conjugated polymer (CP) materials that are considered as an attractive choice for various electronic and optoelectronic applications possess highly heterogeneous complex structures that can span several orders of magnitude in length scale. This is due to the intricate coupling effects of weak secondary interactions and entropic forces that determine molecular organization in bulk polymer materials. Understanding the influence of molecular interactions on the emergence and evolution of nano- and microscale structures is of paramount importance to the guided design and development of condensed CP materials. Such understanding is even more critical for the rational design of hierarchical systems away from equilibrium, where weak molecular interactions can guide the system along competing kinetic pathways toward local energy minima and metastable architectures. In this work, we studied a promising concept for accessing various kinetically stabilized semi-crystalline CP nanostructures that are formed in the process of controlled chain-growth Kumada catalyst-transfer polymerization initiated by a small-molecule catalytic species which can exist in equilibrium between free and aggregated states. Specifically, we chose a small-molecule perylenedicarboximide (PDCI) polymerization catalytic initiator which has a strong tendency toward reversible supramolecular assembly–disassembly that can be controlled by temperature. Addition of a thiophene monomer to a solution of the PDCI initiator starts the chain-growth polymerization process, which produces distinct nanoscale semi-crystalline polythiophene structures formed under predominant kinetic control. Furthermore, we demonstrated that, depending on the reaction temperature (which affects the fine balance between the position of PDCI assembly–disassembly equilibrium, rate of polymerization, and solvent–solute interactions for the growing polythiophene chains), a range of kinetically trapped hierarchically organized semi-crystalline CP systems with substantially varying optoelectronic properties could be obtained. In addition to spectroscopic and electron microscopic studies, in order to better reveal the structural aspects of the generated polymer nanoscale systems, we carried out a series of X-ray diffraction and neutron scattering experiments which indicated complex hierarchical organization in these kinetically stabilized CP assembled materials. We expect that this in situ polymerization-based approach can lead to a general way to expand access to various semi-crystalline CP nanostructured materials with broadly tunable electronic and optical properties.},
doi = {10.1021/acs.macromol.0c02774},
journal = {Macromolecules},
number = 5,
volume = 54,
place = {United States},
year = {Fri Feb 12 00:00:00 EST 2021},
month = {Fri Feb 12 00:00:00 EST 2021}
}
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Chemical and Biomolecule Sensing with Organic Field-Effect Transistors
journal, November 2018

Conjugated polymers – Problems and promises
journal, January 2020

Controllable Processes for Generating Large Single Crystals of Poly(3-hexylthiophene)
journal, September 2012

  • Rahimi, Khosrow; Botiz, Ioan; Stingelin, Natalie
  • Angewandte Chemie International Edition, Vol. 51, Issue 44
  • DOI: 10.1002/anie.201205653

Highly Fluorescent Semiconducting Polymer Dots for Biology and Medicine
journal, January 2013

  • Wu, Changfeng; Chiu, Daniel T.
  • Angewandte Chemie International Edition, Vol. 52, Issue 11
  • DOI: 10.1002/anie.201205133

X-ray scattering from poly(thiophene): crystallinity and crystallographic structure
journal, October 1985

Development of catalyst-transfer condensation polymerization. Synthesis of π-conjugated polymers with controlled molecular weight and low polydispersity
journal, January 2007

  • Miyakoshi, Ryo; Yokoyama, Akihiro; Yokozawa, Tsutomu
  • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 46, Issue 3
  • DOI: 10.1002/pola.22389

Multicolor Conjugated Polymer Dots for Biological Fluorescence Imaging
journal, November 2008

  • Wu, Changfeng; Bull, Barbara; Szymanski, Craig
  • ACS Nano, Vol. 2, Issue 11
  • DOI: 10.1021/nn800590n

Chain Growth Mechanism for Regioregular Nickel-Initiated Cross-Coupling Polymerizations
journal, May 2004

  • Sheina, Elena E.; Liu, Jinsong; Iovu, Mihaela Corina
  • Macromolecules, Vol. 37, Issue 10
  • DOI: 10.1021/ma0357063

Pathway Control in Cooperative vs. Anti‐Cooperative Supramolecular Polymers
journal, August 2019

  • Herkert, Lorena; Droste, Jörn; Kartha, Kalathil K.
  • Angewandte Chemie International Edition, Vol. 58, Issue 33
  • DOI: 10.1002/anie.201905064

Supramolecular Construction of Optoelectronic Biomaterials
journal, March 2013

  • Tovar, John D.
  • Accounts of Chemical Research, Vol. 46, Issue 7
  • DOI: 10.1021/ar3002969

Correlations between Structure and Far-Infrared Active Modes in Polythiophenes
journal, September 2008

  • Hermet, P.; Bantignies, J. -L.; Almairac, R.
  • The Journal of Physical Chemistry B, Vol. 112, Issue 40
  • DOI: 10.1021/jp804813p

Donor–Acceptor‐Conjugated Polymer for High‐Performance Organic Field‐Effect Transistors: A Progress Report
journal, August 2019

  • Kim, Minjun; Ryu, Seung Un; Park, Sang Ah
  • Advanced Functional Materials, Vol. 30, Issue 20
  • DOI: 10.1002/adfm.201904545

π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications †
journal, February 2011

Tuning Structure–Function Properties of π-Conjugated Superstructures by Redox-Assisted Self-Assembly
journal, March 2018

How to Distinguish Isodesmic from Cooperative Supramolecular Polymerisation
journal, January 2010

  • Smulders, Maarten M.  J.; Nieuwenhuizen, Marko M.  L.; de Greef, Tom F.  A.
  • Chemistry - A European Journal, Vol. 16, Issue 1
  • DOI: 10.1002/chem.200902415

Self-Assembled Amphiphilic Diketopyrrolopyrrole-Based Oligothiophenes for Field-Effect Transistors and Solar Cells
journal, May 2011

  • Mei, Jianguo; Graham, Kenneth R.; Stalder, Romain
  • Chemistry of Materials, Vol. 23, Issue 9
  • DOI: 10.1021/cm1036869

High-performance conjugated polymer donor materials for polymer solar cells with narrow-bandgap nonfullerene acceptors
journal, January 2019

  • Cui, Chaohua; Li, Yongfang
  • Energy & Environmental Science, Vol. 12, Issue 11
  • DOI: 10.1039/c9ee02531f
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