Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Topology and ground state control in open-shell donor-acceptor conjugated polymers

Journal Article · · Cell Reports Physical Science
 [1];  [2];  [2];  [3];  [2];  [2];  [2];  [2];  [2];  [3];  [2]
  1. University of Southern Mississippi, Hattiesburg, MS (United States); School of Polymer Science and Engineering, Center for Optoelectronic Materials and Devices, The University of Southern Mississippi, Hattiesburg, MS 39406, USA.
  2. University of Southern Mississippi, Hattiesburg, MS (United States)
  3. University of Alabama, Tuscaloosa, AL (United States)

Donor-acceptor (DA) conjugated polymers (CPs) with narrow bandgaps and open-shell (diradical) character represent an emerging class of materials whose rich behavior emanates from their collective electronic properties and diminished electron pairing. However, the structural and electronic heterogeneities that define these materials complicate bandgap control at low energies and connections linking topology, exchange interactions, and (opto)electronic functionality remain nascent. To address these challenges, we demonstrate structurally rigid and strongly π-conjugated copolymers comprised of a solubilizing thiadiazoloquinoxaline acceptor and cyclopenta[2,1-b:3,4-b']dithiophene or dithieno[3,2-b:2',3'-d]thiophene donors. Atom-specific substitution modulates local aromatic character within the donor resulting in dramatic differences in structural, physicochemical, electronic, and magnetic properties of the polymers. These long-range π-mediated interactions facilitate control between low-spin aromatic and high-spin quinoidal forms. This work provides a strategy to understand the evolution of the electronic structure within DA CPs, control the ground state spin multiplicity, tune spin-spin interactions, and articulate the emergence of their novel properties.

Research Organization:
University of Southern Mississippi, Hattiesburg, MS (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES); Air Force Office of Scientific Research (AFOSR)
Grant/Contract Number:
SC0019361
OSTI ID:
1985337
Journal Information:
Cell Reports Physical Science, Journal Name: Cell Reports Physical Science Journal Issue: 6 Vol. 2; ISSN 2666-3864
Publisher:
ElsevierCopyright Statement
Country of Publication:
United States
Language:
English

References (71)

Open‐Shell Donor–Acceptor Conjugated Polymers with High Electrical Conductivity journal May 2020
On-Surface Synthesis of Atomically Precise Graphene Nanoribbons journal February 2016
Wide Potential Window Supercapacitors Using Open‐Shell Donor–Acceptor Conjugated Polymers with Stable N‐Doped States journal October 2019
The Electronic Properties of Diradicals journal February 1972
On the Biradicaloid Nature of Long Quinoidal Oligothiophenes: Experimental Evidence Guided by Theoretical Studies journal December 2007
Air-Stable n-Type Thermoelectric Materials Enabled by Organic Diradicaloids journal March 2019
Learning how to fine‐tune diradical properties by structure refinement journal July 2020
Importance of unpaired electrons in organic electronics journal August 2014
Open-Shell-Character-Based Molecular Design Principles: Applications to Nonlinear Optics and Singlet Fission journal August 2016
Theory and practice of uncommon molecular electronic configurations: Uncommon molecular electronic configurations
  • Gryn'ova, Ganna; Coote, Michelle L.; Corminboeuf, Clemence
  • Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 5, Issue 6 https://doi.org/10.1002/wcms.1233
journal October 2015
Para-Quinodimethanes: A Unified Review of the Quinoidal-Versus-Aromatic Competition and its Implications journal July 2017
Rylene Ribbons with Unusual Diradical Character journal January 2017
Diindenoanthracene Diradicaloids Enable Rational, Incremental Tuning of Their Singlet-Triplet Energy Gaps journal June 2020
Persistent and Stable Organic Radicals: Design, Synthesis, and Applications journal February 2021
Designing π-conjugated polymers for organic electronics journal December 2013
Molecular Electrical Doping of Organic Semiconductors: Fundamental Mechanisms and Emerging Dopant Design Rules journal February 2016
Controlling a Chemical Coupling Reaction on a Surface: Tools and Strategies for On-Surface Synthesis journal March 2019
Topology, Distance, and Orbital Symmetry Effects on Electronic Spin–Spin Couplings in Rigid Molecular Systems: Implications for Long-Distance Spin–Spin Interactions journal August 2020
A Review on the Origin of Synthetic Metal Radical: Singlet Open-Shell Radical Ground State? journal April 2017
50th Anniversary Perspective : Conducting/Semiconducting Conjugated Polymers. A Personal Perspective on the Past and the Future journal June 2017
Thermoelectric Performance of an Open-Shell Donor–Acceptor Conjugated Polymer Doped with a Radical-Containing Small Molecule journal May 2018
High Spin Pro-Quinoid Benzo[1,2-c;4,5-c′]bisthiadiazole Conjugated Polymers for High-Performance Solution-Processable Polymer Thermoelectrics journal January 2020
Nanographene and Graphene Edges: Electronic Structure and Nanofabrication journal November 2012
Zethrenes, Extended p -Quinodimethanes, and Periacenes with a Singlet Biradical Ground State journal July 2014
Organic Diradicals and Polyradicals: From Spin Coupling to Magnetism? journal June 1994
Anisotropy of the Induced Current Density (ACID), a General Method To Quantify and Visualize Electronic Delocalization journal October 2005
Diradicals journal July 2013
The double (or dynamic) spin polarization in π diradicals journal October 1989
The role of orbital interactions in determining ferromagnetic coupling in organic molecular assemblies journal July 1995
Intermolecular Covalent π−π Bonding Interaction Indicated by Bond Distances, Energy Bands, and Magnetism in Biphenalenyl Biradicaloid Molecular Crystal journal February 2007
Synthesis and Characterization of Teranthene: A Singlet Biradical Polycyclic Aromatic Hydrocarbon Having Kekulé Structures journal August 2010
Pushing Extended p -Quinodimethanes to the Limit: Stable Tetracyano-oligo( N -annulated perylene)quinodimethanes with Tunable Ground States journal April 2013
Efficient Singlet Fission and Triplet-Pair Emission in a Family of Zethrene Diradicaloids journal December 2017
High-Spin Organic Molecules journal January 2015
Amino(oligo)thiophene-Based Environmentally Sensitive Biomembrane Chromophores journal July 2008
Rational Design of High-Spin Biradicaloids in the Isobenzofulvene and Isobenzoheptafulvene Series journal May 2012
Diradical Character View of Singlet Fission journal December 2011
Thiadiazoloquinoxalines: Tuning Physical Properties through Smart Synthesis journal March 2011
Room-temperature magnetic order on zigzag edges of narrow graphene nanoribbons journal October 2014
On-surface synthesis of graphene nanoribbons with zigzag edge topology journal March 2016
Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals journal May 2016
Synthetic organic spin chemistry for structurally well-defined open-shell graphene fragments journal February 2011
Tuning the effective spin-orbit coupling in molecular semiconductors journal May 2017
Organic tailored batteries materials using stable open-shell molecules with degenerate frontier orbitals journal October 2011
Prediction of very large values of magnetoresistance in a graphene nanoribbon device journal June 2008
Open-shell organic semiconductors: an emerging class of materials with novel properties journal May 2018
Thiophene and its sulfur inhibit indenoindenodibenzothiophene diradicals from low-energy lying thermal triplets journal September 2018
Magnetic edge states and coherent manipulation of graphene nanoribbons journal May 2018
Heteroannulated acceptors based on benzothiadiazole journal January 2015
Pro-aromatic and anti-aromatic π-conjugated molecules: an irresistible wish to be diradicals journal January 2015
Achieving a solar power conversion efficiency exceeding 9% by modifying the structure of a simple, inexpensive and highly scalable polymer journal January 2016
From open-shell singlet diradicaloids to polyradicaloids journal January 2018
The electronic applications of stable diradicaloids: present and future journal January 2018
Quinoidal conjugated polymers with open-shell character journal January 2021
Molecular spintronics journal January 2011
Quinoidal oligothiophenes: new properties behind an unconventional electronic structure journal January 2012
Low band gap polycyclic hydrocarbons: from closed-shell near infrared dyes and semiconductors to open-shell radicals journal January 2012
Strong acceptors in donor–acceptor polymers for high performance thin film transistors journal January 2013
Comparative studies on the electrochemical and optical properties of representative benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole, [1,2,5]-thiadiazolo[3,4-g]quinoxaline and pyrazino[2,3-g]quinoxaline derivatives journal January 2013
Organic and molecular magnets journal June 2004
Anomalous paramagnetism of copper acetate
  • Bleaney, Brebis; Powers, K. D.
  • Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences, Vol. 214, Issue 1119, p. 451-465 https://doi.org/10.1098/rspa.1952.0181
journal October 1952
Envelope Modulation in Spin-Echo Experiments journal April 1972
A high-spin ground-state donor-acceptor conjugated polymer journal May 2019
Atomically precise bottom-up synthesis of π-extended [5]triangulene journal July 2019
Fully Conjugated Porphyrin Tapes with Electronic Absorption Bands That Reach into Infrared journal July 2001
Magnetic Ordering in an Organic Polymer journal November 2001
Quantum units from the topological engineering of molecular graphenoids journal November 2019
Novel Electron Acceptors Bearing a Heteroquinonoid System. I. Synthesis and Conductive Complexes of 5,5′-Bis(dicyanomethylene)-5,5′-dihydro-Δ2,2′-bithiophene and Related Compounds journal May 1989
Organic Magnets journal November 2000
Recent Advances in Organic Radicals and Their Magnetism journal November 2016
Tetracyanoquinodimethanes Fused with 1,2,5-Thiadiazole and Pyrazine Units journal January 1992