Quinonoid vs. aromatic structures of heteroconjugated polymers from oligomer calculations

Grover, Girishma; Peters, Garvin M.; Tovar, John D.; Kertesz, Miklos

doi:10.1039/d0cp00606h

Quinonoid vs. aromatic structures of heteroconjugated polymers from oligomer calculations

Journal Article · Wed Apr 29 00:00:00 EDT 2020 · Physical Chemistry Chemical Physics. PCCP

DOI:https://doi.org/10.1039/d0cp00606h· OSTI ID:1803495

Grover, Girishma ^[1]; ^[2]; ^[3]; ^[4]

Georgetown Univ., Washington, DC (United States). Chemistry Dept. Inst. of Soft Matter; OSTI
Johns Hopkins Univ., Baltimore, MD (United States). Dept. of Chemistry
Johns Hopkins Univ., Baltimore, MD (United States). Dept. of Chemistry. Dept. of Materials Science and Engineering
Georgetown Univ., Washington, DC (United States). Chemistry Dept. Inst. of Soft Matter

Conjugated polymers with quinonoid ground states can display low optical band gaps. The design of novel conjugated polymers with quinonoid ground states offers insights into the relative stabilities of aromatic vs. quinonoid structures. In this work, we present parameters such as the quinonoid (Q)/aromatic (A) energy difference, the band gap, and the C–C distances between the repeat units. This study reveals eight new polymers which exist in quinonoid ground state among twenty-nine polymers of varying structural composition that were subject to analysis. We expect that copolymerizing such quinonoid ground state monomers with aromatic ground state monomers will modulate the bandgap of the resulting polymers.

View Accepted Manuscript (DOE)

Research Organization:: Georgetown Univ., Washington, DC (United States); Johns Hopkins Univ., Baltimore, MD (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0019017

OSTI ID:: 1803495

Alternate ID(s):: OSTI ID: 1617918
OSTI ID: 1864953
OSTI ID: 1906719

Journal Information:: Physical Chemistry Chemical Physics. PCCP, Journal Name: Physical Chemistry Chemical Physics. PCCP Journal Issue: 20 Vol. 22; ISSN 1463-9076

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (33)

Electronic Tuning of Mixed Quinoidal‐Aromatic Conjugated Polyelectrolytes: Direct Ionic Substitution on Polymer Main‐Chains Anderson, Christopher L.; Dai, Nan; Teat, Simon J. Angewandte Chemie International Edition, Vol. 58, Issue 50 https://doi.org/10.1002/anie.201908609	journal	December 2019
Optoelectronic properties of thiazole-based polythiophenes Camurlu, Pinar; Guven, Nese Journal of Applied Polymer Science, Vol. 132, Issue 27 https://doi.org/10.1002/app.42206	journal	March 2015
The effect of additional fused rings on the stabilities and the band gaps of heteroconjugated polymers Lee, Yong S.; Kertesz, Miklos International Journal of Quantum Chemistry, Vol. 32, Issue S21 https://doi.org/10.1002/qua.560320719	journal	March 1987
The influence of polarization functions on molecular orbital hydrogenation energies Hariharan, P. C.; Pople, J. A. Theoretica Chimica Acta, Vol. 28, Issue 3 https://doi.org/10.1007/BF00533485	journal	January 1973
Processable low band gap π-conjugated polymer, poly(isothianaphthene) Chen, Show-An; Lee, Chin-Chang Polymer, Vol. 37, Issue 3 https://doi.org/10.1016/0032-3861(96)82924-7	journal	February 1996
Bandgap calculations for conjugated polymers Yang, Shujiang; Olishevski, Pavel; Kertesz, Miklos Synthetic Metals, Vol. 141, Issue 1-2 https://doi.org/10.1016/j.synthmet.2003.08.019	journal	March 2004
Simple Extrapolation Method To Predict the Electronic Structure of Conjugated Polymers from Calculations on Oligomers Larsen, Ross E. The Journal of Physical Chemistry C, Vol. 120, Issue 18 https://doi.org/10.1021/acs.jpcc.6b02138	journal	April 2016
Benzotriazole-Containing Planar Conjugated Polymers with Noncovalent Conformational Locks for Thermally Stable and Efficient Polymer Field-Effect Transistors Yum, Seungjib; An, Tae Kyu; Wang, Xiaowei Chemistry of Materials, Vol. 26, Issue 6 https://doi.org/10.1021/cm4042346	journal	March 2014
Aromaticity from the Viewpoint of Molecular Geometry: Application to Planar Systems Krygowski, Tadeusz M.; Szatylowicz, Halina; Stasyuk, Olga A. Chemical Reviews, Vol. 114, Issue 12 https://doi.org/10.1021/cr400252h	journal	April 2014
Conjugated Polymers and Aromaticity Kertesz, Miklos; Choi, Cheol Ho; Yang, Shujiang Chemical Reviews, Vol. 105, Issue 10 https://doi.org/10.1021/cr990357p	journal	October 2005
Energetics and geometry of conducting polymers from oligomers Karpfen, Alfred; Kertesz, Miklos The Journal of Physical Chemistry, Vol. 95, Issue 20 https://doi.org/10.1021/j100173a024	journal	October 1991
Energy gap and bond length alternation in heterosubstituted narrow gap semiconducting polymers Kertesz, Miklos.; Lee, Yong S. The Journal of Physical Chemistry, Vol. 91, Issue 11 https://doi.org/10.1021/j100295a007	journal	May 1987
Poly(2,7-dibenzosilole): A Blue Light Emitting Polymer Chan, Khai Leok; McKiernan, Mary J.; Towns, Carl R. Journal of the American Chemical Society, Vol. 127, Issue 21 https://doi.org/10.1021/ja0508065	journal	June 2005
Controlling Conformations of Conjugated Polymers and Small Molecules: The Role of Nonbonding Interactions Jackson, Nicholas E.; Savoie, Brett M.; Kohlstedt, Kevin L. Journal of the American Chemical Society, Vol. 135, Issue 28 https://doi.org/10.1021/ja403667s	journal	May 2013
Poly(isothianaphthene) Wudl, Fred; Kobayashi, M.; Heeger, A. J. The Journal of Organic Chemistry, Vol. 49, Issue 18 https://doi.org/10.1021/jo00192a027	journal	September 1984
Interplay of Conformational States and Nonbonded Interactions in Substituted Bithiophenes Raos, Guido; Famulari, Antonino; Meille, Stefano V. The Journal of Physical Chemistry A, Vol. 108, Issue 4 https://doi.org/10.1021/jp036614i	journal	January 2004
Reviewing Extrapolation Procedures of the Electronic Properties on the π-Conjugated Polymer Limit Torras, Juan; Casanovas, Jordi; Alemán, Carlos The Journal of Physical Chemistry A, Vol. 116, Issue 28 https://doi.org/10.1021/jp303584b	journal	July 2012
A Robust Low Band Gap Processable n-Type Conducting Polymer Based on Poly(isothianaphthene) Meng, H.; Wudl, F. Macromolecules, Vol. 34, Issue 6 https://doi.org/10.1021/ma001689v	journal	March 2001
Highly Luminescent 1,4-Diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole- (DPP-) Based Conjugated Polymers Prepared Upon Suzuki Coupling Zhu, Y.; Rabindranath, A. R.; Beyerlein, T. Macromolecules, Vol. 40, Issue 19 https://doi.org/10.1021/ma0710941	journal	September 2007
Low Band Gap Polymers Design Approach Based on a Mix of Aromatic and Quinoid Structures Bérubé, Nicolas; Gaudreau, Josiane; Côté, Michel Macromolecules, Vol. 46, Issue 17 https://doi.org/10.1021/ma401358r	journal	August 2013
A class of narrow-band-gap semiconducting polymers Jenekhe, Samson A. Nature, Vol. 322, Issue 6077 https://doi.org/10.1038/322345a0	journal	July 1986
Light-emitting diodes based on conjugated polymers Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R. Nature, Vol. 347, Issue 6293 https://doi.org/10.1038/347539a0	journal	October 1990
Highly Efficient and Stable Solar Cells Based on Thiazolothiazole and Naphthobisthiadiazole Copolymers Saito, Masahiko; Osaka, Itaru; Suzuki, Yasuhito Scientific Reports, Vol. 5, Issue 1 https://doi.org/10.1038/srep14202	journal	September 2015
Synthesis and properties of pyrrolo[3,4-c]pyrrole-1,3-dione based polymer semiconductors and their performance in organic thin film transistors Guo, Chang; Sun, Bin; Li, Yuning Polym. Chem., Vol. 5, Issue 18 https://doi.org/10.1039/C4PY00372A	journal	January 2014
Development of a quantum chemical descriptor expressing aromatic/quinoidal character for designing narrow-bandgap π-conjugated polymers Hayashi, Yoshihiro; Kawauchi, Susumu Polymer Chemistry, Vol. 10, Issue 41 https://doi.org/10.1039/C9PY00987F	journal	January 2019
Soluble and processable regioregular poly(3‐hexylthiophene) for thin film field‐effect transistor applications with high mobility Bao, Zhenan; Dodabalapur, Ananth; Lovinger, Andrew J. Applied Physics Letters, Vol. 69, Issue 26, p. 4108-4110 https://doi.org/10.1063/1.117834	journal	December 1996
Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules Hehre, W. J.; Ditchfield, R.; Pople, J. A. The Journal of Chemical Physics, Vol. 56, Issue 5, p. 2257-2261 https://doi.org/10.1063/1.1677527	journal	March 1972
Investigation of annealing effects and film thickness dependence of polymer solar cells based on poly(3-hexylthiophene) Li, Gang; Shrotriya, Vishal; Yao, Yan Journal of Applied Physics, Vol. 98, Issue 4 https://doi.org/10.1063/1.2008386	journal	August 2005
Towards organic polymers with very small intrinsic band gaps. I. Electronic structure of polyisothianaphthene and derivatives Brédas, J. L.; Heeger, A. J.; Wudl, F. The Journal of Chemical Physics, Vol. 85, Issue 8 https://doi.org/10.1063/1.451741	journal	October 1986
Quinoid vs aromatic structure of polyisothianaphthene Kürti, J.; Surján, P. R. The Journal of Chemical Physics, Vol. 92, Issue 5 https://doi.org/10.1063/1.457883	journal	March 1990
Toward reliable density functional methods without adjustable parameters: The PBE0 model Adamo, Carlo; Barone, Vincenzo The Journal of Chemical Physics, Vol. 110, Issue 13 https://doi.org/10.1063/1.478522	journal	April 1999
Highly sensitive biological and chemical sensors based on reversible fluorescence quenching in a conjugated polymer Chen, L.; McBranch, D. W.; Wang, H. -L. Proceedings of the National Academy of Sciences, Vol. 96, Issue 22 https://doi.org/10.1073/pnas.96.22.12287	journal	October 1999
Conducting Polymers and their Applications Ates, Murat; Karazehir, Tolga; Sezai Sarac, A. Current Physical Chemistry, Vol. 2, Issue 3 https://doi.org/10.2174/1877946811202030224	journal	May 2012

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