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Title: Synthesis and optoelectronic properties of benzodithiophene-based conjugated polymers with hydrogen bonding nucleobase side chain functionality

Abstract

Nucleobase functionalities in conjugated, alternating copolymers participate in interbase hydrogen bonding, which promotes molecular assembly and organization in thin films and enhances optical and electronic properties.

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [2]
  1. Department of Chemistry, University of Tennessee – Knoxville, Knoxville, USA
  2. Department of Chemistry, University of North Carolina – Charlotte, Charlotte, USA
  3. Department of Chemistry, University of Tennessee – Knoxville, Knoxville, USA, Department of Chemical & Biomolecular Engineering
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1647399
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Polymer Chemistry
Additional Journal Information:
Journal Name: Polymer Chemistry Journal Volume: 11 Journal Issue: 36; Journal ID: ISSN 1759-9954
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Sabury, Sina, Adams, Tyler J., Kocherga, Margaret, Kilbey, S. Michael, and Walter, Michael G. Synthesis and optoelectronic properties of benzodithiophene-based conjugated polymers with hydrogen bonding nucleobase side chain functionality. United Kingdom: N. p., 2020. Web. doi:10.1039/D0PY00972E.
Sabury, Sina, Adams, Tyler J., Kocherga, Margaret, Kilbey, S. Michael, & Walter, Michael G. Synthesis and optoelectronic properties of benzodithiophene-based conjugated polymers with hydrogen bonding nucleobase side chain functionality. United Kingdom. https://doi.org/10.1039/D0PY00972E
Sabury, Sina, Adams, Tyler J., Kocherga, Margaret, Kilbey, S. Michael, and Walter, Michael G. Tue . "Synthesis and optoelectronic properties of benzodithiophene-based conjugated polymers with hydrogen bonding nucleobase side chain functionality". United Kingdom. https://doi.org/10.1039/D0PY00972E.
@article{osti_1647399,
title = {Synthesis and optoelectronic properties of benzodithiophene-based conjugated polymers with hydrogen bonding nucleobase side chain functionality},
author = {Sabury, Sina and Adams, Tyler J. and Kocherga, Margaret and Kilbey, S. Michael and Walter, Michael G.},
abstractNote = {Nucleobase functionalities in conjugated, alternating copolymers participate in interbase hydrogen bonding, which promotes molecular assembly and organization in thin films and enhances optical and electronic properties.},
doi = {10.1039/D0PY00972E},
journal = {Polymer Chemistry},
number = 36,
volume = 11,
place = {United Kingdom},
year = {Tue Sep 22 00:00:00 EDT 2020},
month = {Tue Sep 22 00:00:00 EDT 2020}
}

Works referenced in this record:

Progressive Macromolecular Self-Assembly: From Biomimetic Chemistry to Bio-Inspired Materials
journal, September 2013


Enhancement of dispersion and bonding of graphene-polymer through wet transfer of functionalized graphene oxide
journal, January 2012


First Phenylenevinylene Based Organogels:  Self-Assembled Nanostructures via Cooperative Hydrogen Bonding and π-Stacking
journal, May 2001

  • Ajayaghosh, A.; George, Subi J.
  • Journal of the American Chemical Society, Vol. 123, Issue 21
  • DOI: 10.1021/ja005933+

Molecular Design of Benzodithiophene-Based Organic Photovoltaic Materials
journal, June 2016


Influence of Alkyl Chain Branching Positions on the Hole Mobilities of Polymer Thin-Film Transistors
journal, September 2012


Determination of the NMR monomer shift and dimerization constant in a self-associating system by direct application of the least-squares method
journal, January 1994

  • Tan, Henry K. S.
  • Journal of the Chemical Society, Faraday Transactions, Vol. 90, Issue 23
  • DOI: 10.1039/ft9949003521

Solvation by aqueous solutions of imidazole-based ionic liquids: 2- A comparison between alkyl and alkoxy side-chains
journal, November 2017


Efficient Supercapacitor Energy Storage Using Conjugated Microporous Polymer Networks Synthesized from Buchwald-Hartwig Coupling
journal, January 2018


A side-chain engineering approach to solvent-resistant semiconducting polymer thin films
journal, January 2016

  • Guo, Zi-Hao; Ai, Na; McBroom, Connor Ryan
  • Polymer Chemistry, Vol. 7, Issue 3
  • DOI: 10.1039/C5PY01669J

Light-Emitting Diodes from Fluorene-Based π-Conjugated Polymers
journal, July 2000

  • Donat-Bouillud, Anne; Lévesque, Isabelle; Tao, Ye
  • Chemistry of Materials, Vol. 12, Issue 7
  • DOI: 10.1021/cm0001298

Modification of Side Chains of Conjugated Molecules and Polymers for Charge Mobility Enhancement and Sensing Functionality
journal, May 2018


Supramolecular polymeric micelles as high performance electrochemical materials
journal, January 2015

  • Cheng, Chih-Chia; Chang, Feng-Chih; Ko, Fu-Hsiang
  • Journal of Materials Chemistry C, Vol. 3, Issue 37
  • DOI: 10.1039/C5TC02130H

Side Chain Engineering in Solution-Processable Conjugated Polymers
journal, September 2013

  • Mei, Jianguo; Bao, Zhenan
  • Chemistry of Materials, Vol. 26, Issue 1
  • DOI: 10.1021/cm4020805

Molecular origin of high field-effect mobility in an indacenodithiophene–benzothiadiazole copolymer
journal, July 2013

  • Zhang, Xinran; Bronstein, Hugo; Kronemeijer, Auke J.
  • Nature Communications, Vol. 4, Issue 1
  • DOI: 10.1038/ncomms3238

Intra-red absorption spectra of the single crystals of 1-methyl-thymine, 9-methyladenine and their 1:1 complex
journal, April 1967

  • Kyogoku, Y.; Higuchi, S.; Tsuboi, M.
  • Spectrochimica Acta Part A: Molecular Spectroscopy, Vol. 23, Issue 4
  • DOI: 10.1016/0584-8539(67)80022-9

Enhanced Solid-State Order and Field-Effect Hole Mobility through Control of Nanoscale Polymer Aggregation
journal, December 2013

  • Chen, Mark S.; Lee, Olivia P.; Niskala, Jeremy R.
  • Journal of the American Chemical Society, Vol. 135, Issue 51
  • DOI: 10.1021/ja4088665

Improving the Performance of P3HT–Fullerene Solar Cells with Side-Chain-Functionalized Poly(thiophene) Additives: A New Paradigm for Polymer Design
journal, February 2012

  • Lobez, Jose M.; Andrew, Trisha L.; Bulović, Vladimir
  • ACS Nano, Vol. 6, Issue 4
  • DOI: 10.1021/nn204589u

Phase Behavior of Adenine-Containing Block Copolymer
journal, December 2018


Synthesis and properties of a new conjugated polymer containing benzodithiophene for polymer solar cells
journal, February 2014


Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications
journal, March 2009

  • Mishra, Amaresh; Ma, Chang-Qi; Bäuerle, Peter
  • Chemical Reviews, Vol. 109, Issue 3
  • DOI: 10.1021/cr8004229

Carrier mobility of organic semiconductors based on current-voltage characteristics
journal, February 2010

  • Wang, Z. B.; Helander, M. G.; Greiner, M. T.
  • Journal of Applied Physics, Vol. 107, Issue 3
  • DOI: 10.1063/1.3305341

Critical Role of Alkyl Chain Branching of Organic Semiconductors in Enabling Solution-Processed N-Channel Organic Thin-Film Transistors with Mobility of up to 3.50 cm 2 V –1 s –1
journal, January 2013

  • Zhang, Fengjiao; Hu, Yunbin; Schuettfort, Torben
  • Journal of the American Chemical Society, Vol. 135, Issue 6
  • DOI: 10.1021/ja311469y

2,7-Carbazole-Based Conjugated Polymers for Blue, Green, and Red Light Emission
journal, October 2002

  • Morin, Jean-François; Leclerc, Mario
  • Macromolecules, Vol. 35, Issue 22
  • DOI: 10.1021/ma020880x

Patternable Conjugated Polymers with Latent Hydrogen-Bonding on the Main Chain
journal, December 2014

  • Yang, Kun; He, Tianda; Chen, Xiaoyi
  • Macromolecules, Vol. 47, Issue 24
  • DOI: 10.1021/ma501960t

Linking design and properties of purine-based donor–acceptor chromophores as optoelectronic materials
journal, January 2017

  • Collier, Graham S.; Brown, Lauren A.; Boone, Evan S.
  • Journal of Materials Chemistry C, Vol. 5, Issue 27
  • DOI: 10.1039/C7TC01835E

Improving the performance of conjugated polymer-based devices by control of interchain interactions and polymer film morphology
journal, April 2000

  • Nguyen, Thuc-Quyen; Kwong, Raymond C.; Thompson, Mark E.
  • Applied Physics Letters, Vol. 76, Issue 17
  • DOI: 10.1063/1.126374

Rational Design of High Performance Conjugated Polymers for Organic Solar Cells
journal, January 2012

  • Zhou, Huaxing; Yang, Liqiang; You, Wei
  • Macromolecules, Vol. 45, Issue 2
  • DOI: 10.1021/ma201648t

Bioinspired Nucleobase-Driven Nonswellable Adhesive and Tough Gel with Excellent Underwater Adhesion
journal, January 2019

  • Liu, Xin; Zhang, Qin; Duan, Lijie
  • ACS Applied Materials & Interfaces, Vol. 11, Issue 6
  • DOI: 10.1021/acsami.8b21686

Improved Performance for Inverted Organic Photovoltaics via Spacer between Benzodithiophene and Benzothiazole in Polymers
journal, August 2015

  • Mohammad, Lal; Chen, Qiliang; Mitul, Abu
  • The Journal of Physical Chemistry C, Vol. 119, Issue 33
  • DOI: 10.1021/acs.jpcc.5b05608

Bandgap and Molecular Energy Level Control of Conjugated Polymer Photovoltaic Materials Based on Benzo[1,2- b :4,5- b ′]dithiophene
journal, August 2008

  • Hou, Jianhui; Park, Mi-Hyae; Zhang, Shaoqing
  • Macromolecules, Vol. 41, Issue 16
  • DOI: 10.1021/ma800820r

Tutorial: Organic field-effect transistors: Materials, structure and operation
journal, August 2018

  • Lamport, Zachary A.; Haneef, Hamna F.; Anand, Sajant
  • Journal of Applied Physics, Vol. 124, Issue 7
  • DOI: 10.1063/1.5042255

Alkyl Side Chain Impact on the Charge Transport and Photovoltaic Properties of Benzodithiophene and Diketopyrrolopyrrole-Based Copolymers
journal, August 2011

  • Li, Zhao; Zhang, Yanguang; Tsang, Sai-Wing
  • The Journal of Physical Chemistry C, Vol. 115, Issue 36
  • DOI: 10.1021/jp202996p

Electrochemical Oxidation of Adenine: A Mixed Adsorption and Diffusion Response on an Edge-Plane Pyrolytic Graphite Electrode
journal, July 2010

  • Gonçalves, Luís M.; Batchelor-McAuley, Christopher; Barros, Aquiles A.
  • The Journal of Physical Chemistry C, Vol. 114, Issue 33
  • DOI: 10.1021/jp1046672

Low Band Gap Donor−Acceptor Conjugated Polymers toward Organic Solar Cells Applications
journal, January 2007

  • Colladet, Kristof; Fourier, Sofie; Cleij, Thomas J.
  • Macromolecules, Vol. 40, Issue 1
  • DOI: 10.1021/ma061760i

Breaking the 10% Efficiency Barrier in Organic Photovoltaics: Morphology and Device Optimization of Well-Known PBDTTT Polymers
journal, March 2016

  • Zhang, Shaoqing; Ye, Long; Hou, Jianhui
  • Advanced Energy Materials, Vol. 6, Issue 11
  • DOI: 10.1002/aenm.201502529

Poly(ethylene glycol)-based ammonium ionenes containing nucleobases
journal, March 2013


High-Mobility Conjugated Polymers Based on Fused-Thiophene Building Blocks
journal, January 2011

  • Liu, Yao; Liu, Yunqi; Zhan, Xiaowei
  • Macromolecular Chemistry and Physics, Vol. 212, Issue 5
  • DOI: 10.1002/macp.201000677

Significant Improvement of Semiconducting Performance of the Diketopyrrolopyrrole–Quaterthiophene Conjugated Polymer through Side-Chain Engineering via Hydrogen-Bonding
journal, December 2015

  • Yao, Jingjing; Yu, Chenmin; Liu, Zitong
  • Journal of the American Chemical Society, Vol. 138, Issue 1
  • DOI: 10.1021/jacs.5b09737

Molecular weight dependence of carrier mobility and recombination rate in neat P3HT films
journal, November 2017

  • Dixon, Alex G.; Visvanathan, Rayshan; Clark, Noel A.
  • Journal of Polymer Science Part B: Polymer Physics, Vol. 56, Issue 1
  • DOI: 10.1002/polb.24531

Biomolecule assisted self-assembly of π-conjugated oligomers
journal, January 2010

  • Jatsch, A.; Schillinger, E. -K.; Schmid, S.
  • Journal of Materials Chemistry, Vol. 20, Issue 18
  • DOI: 10.1039/b926594e

Towards optimization of device performance in conjugated polymer photovoltaics: Charge generation, transfer and transport in poly(p-phenylene-vinylene) polymer heterojunctions
journal, June 2008

  • Chasteen, Stephanie V.; Sholin, Veronica; Carter, Sue A.
  • Solar Energy Materials and Solar Cells, Vol. 92, Issue 6
  • DOI: 10.1016/j.solmat.2008.01.014

Solvent free oxidative coupling polymerization of 3-hexylthiophene (3HT) in the presence of FeCl 3 particles
journal, January 2016

  • Hirai, T.; Nagae, Y.; White, K. L.
  • RSC Advances, Vol. 6, Issue 113
  • DOI: 10.1039/C6RA23178K

Synthesis and Photovoltaic Properties of Two Benzo[1,2- b :3,4- b′ ]dithiophene-Based Conjugated Polymers
journal, November 2009

  • Hou, Jianhui; Chen, Hsiang-Yu; Zhang, Shaoqing
  • The Journal of Physical Chemistry C, Vol. 113, Issue 50
  • DOI: 10.1021/jp9060413

A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons
journal, August 1949

  • Benesi, H. A.; Hildebrand, J. H.
  • Journal of the American Chemical Society, Vol. 71, Issue 8
  • DOI: 10.1021/ja01176a030

Advances in Charge Carrier Mobilities of Semiconducting Polymers Used in Organic Transistors
journal, September 2013

  • Holliday, Sarah; Donaghey, Jenny E.; McCulloch, Iain
  • Chemistry of Materials, Vol. 26, Issue 1
  • DOI: 10.1021/cm402421p

Specific Recognition of Nucleobase-Functionalized Polythiophenes
journal, March 1998


Nanostructured Conjugated Polymers: Toward High-Performance Organic Electrodes for Rechargeable Batteries
journal, August 2017


Developments of Diketopyrrolopyrrole‐Dye‐Based Organic Semiconductors for a Wide Range of Applications in Electronics
journal, December 2019

  • Liu, Qian; Bottle, Steven E.; Sonar, Prashant
  • Advanced Materials, Vol. 32, Issue 4
  • DOI: 10.1002/adma.201903882

Synthesis of a soluble adenine-functionalized polythiophene through direct arylation polymerization and its fluorescence responsive behavior
journal, January 2020

  • Sabury, Sina; Collier, Graham S.; Ericson, M. Nance
  • Polymer Chemistry, Vol. 11, Issue 4
  • DOI: 10.1039/C9PY01142K

Nucleobase-functionalized acrylic ABA triblock copolymers and supramolecular blends
journal, January 2015

  • Zhang, Keren; Aiba, Motohiro; Fahs, Gregory B.
  • Polymer Chemistry, Vol. 6, Issue 13
  • DOI: 10.1039/C4PY01798F

Nucleobase Containing Synthetic Polymers: Advancing Biomimicry via Controlled Synthesis and Self-Assembly
journal, August 2012

  • McHale, Ronan; O’Reilly, Rachel K.
  • Macromolecules, Vol. 45, Issue 19
  • DOI: 10.1021/ma300895u

The Hydrogen Bond in the Solid State
journal, January 2002


Polymer Side-Chain Variation Induces Microstructural Disparity in Nonfullerene Solar Cells
journal, December 2018


Charge Transport in Organic Semiconductors
journal, April 2007

  • Coropceanu, Veaceslav; Cornil, Jérôme; da Silva Filho, Demetrio A.
  • Chemical Reviews, Vol. 107, Issue 4
  • DOI: 10.1021/cr050140x

Immobilization Strategies for Organic Semiconducting Conjugated Polymers
journal, May 2018


Complementary hydrogen bonding interaction-mediated hole injection in organic light-emitting devices
journal, January 2017

  • Cheng, Chih-Chia; Chu, Chih-Wei; Huang, Jyun-Jie
  • Journal of Materials Chemistry C, Vol. 5, Issue 19
  • DOI: 10.1039/C7TC00693D

Synthesis, Optical Properties, and Electronic Structures of Nucleobase-Containing π-Conjugated Oligomers
journal, January 2015

  • Bou Zerdan, Raghida; Cohn, Pamela; Puodziukynaite, Egle
  • The Journal of Organic Chemistry, Vol. 80, Issue 3
  • DOI: 10.1021/jo502773g

Bioinspired hole-conducting polymers for application in organic light-emitting diodes
journal, January 2012

  • Cheng, Chih-Chia; Chu, Yu-Lin; Huang, Pei-Hsiu
  • Journal of Materials Chemistry, Vol. 22, Issue 35
  • DOI: 10.1039/c2jm32665e

Chlorinated Wide-Bandgap Donor Polymer Enabling Annealing Free Nonfullerene Solar Cells with the Efficiency of 11.5%
journal, November 2018


Enhancing the Performance of Solution-Processed Bulk-Heterojunction Solar Cells Using Hydrogen-Bonding-Induced Self-Organization of Small Molecules
journal, November 2013

  • Lam, Kwan Hang; Foong, Thelese Ru Bao; Ooi, Zi En
  • ACS Applied Materials & Interfaces, Vol. 5, Issue 24
  • DOI: 10.1021/am4042614

Progress in Drying Technology for Nanomaterials
journal, February 2005


Fine-tuning solid state packing and significantly improving photovoltaic performance of conjugated polymers through side chain engineering via random polymerization
journal, January 2017

  • Wang, Xinlong; Deng, Wei; Chen, Yusheng
  • Journal of Materials Chemistry A, Vol. 5, Issue 11
  • DOI: 10.1039/C6TA10864D

Emerging Design and Characterization Guidelines for Polymer-Based Infrared Photodetectors
journal, December 2018


F.t.-i.r. and laser-Raman spectra of adenine and adenosine
journal, August 1984


Guanosine-based Hydrogen-bonded Scaffolds: Controlling the Assembly of Oligothiophenes
journal, June 2008

  • Spada, Gian Piero; Lena, Stefano; Masiero, Stefano
  • Advanced Materials, Vol. 20, Issue 12
  • DOI: 10.1002/adma.200703177

Hydrogen-bonded Supramolecular π-Functional Materials
journal, February 2011

  • González-Rodríguez, David; Schenning, Albertus P. H. J.
  • Chemistry of Materials, Vol. 23, Issue 3
  • DOI: 10.1021/cm101817h

Self-Organizing Oligothiophene−Nucleoside Conjugates:  Versatile Synthesis via “Click”-Chemistry
journal, March 2008

  • Jatsch, Anja; Kopyshev, Alexey; Mena-Osteritz, Elena
  • Organic Letters, Vol. 10, Issue 5
  • DOI: 10.1021/ol703090f

Spontaneous self-association of adenine and uracil in polycrystals from low temperature FTIR spectra in the range below 1000cm−1
journal, November 2005

  • Rozenberg, M.; Shoham, G.; Reva, I.
  • Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 62, Issue 1-3
  • DOI: 10.1016/j.saa.2004.12.037

F.t.-i.r. and laser-Raman spectra of thymine and thymidine
journal, November 1984


Synthesis of Main Chain Purine-Based Copolymers and Effects of Monomer Design on Thermal and Optical Properties
journal, May 2016


Record High Hole Mobility in Polymer Semiconductors via Side-Chain Engineering
journal, September 2013

  • Kang, Il; Yun, Hui-Jun; Chung, Dae Sung
  • Journal of the American Chemical Society, Vol. 135, Issue 40
  • DOI: 10.1021/ja405112s

Novel Method for Concentrating and Drying Polymeric Nanoparticles: Hydrogen Bonding Coacervate Precipitation
journal, January 2010

  • D’Addio, Suzanne M.; Kafka, Concepcion; Akbulut, Mustafa
  • Molecular Pharmaceutics, Vol. 7, Issue 2
  • DOI: 10.1021/mp900260q

Iterative determination of the NMR monomer shift and dimerization constant in a self-associating system
journal, April 1985

  • Chen, Jenn Shing; Shirts, Randall B.
  • The Journal of Physical Chemistry, Vol. 89, Issue 9
  • DOI: 10.1021/j100255a018

A Wide Band Gap Polymer with a Deep Highest Occupied Molecular Orbital Level Enables 14.2% Efficiency in Polymer Solar Cells
journal, May 2018

  • Li, Sunsun; Ye, Long; Zhao, Wenchao
  • Journal of the American Chemical Society, Vol. 140, Issue 23
  • DOI: 10.1021/jacs.8b02695

An all-conjugated gradient copolymer approach for morphological control of polymer solar cells
journal, January 2015

  • Amonoo, Jojo A.; Li, Anton; Purdum, Geoffrey E.
  • Journal of Materials Chemistry A, Vol. 3, Issue 40
  • DOI: 10.1039/C5TA04752H

Self-Complementary Nucleoside-Thiophene Hybrid Systems: Synthesis and Supramolecular Organization: Self-Complementary Nucleoside-Thiophene Hybrid Systems: …
journal, December 2009

  • Navacchia, Maria Luisa; Favaretto, Laura; Treossi, Emanuele
  • Macromolecular Rapid Communications, Vol. 31, Issue 4
  • DOI: 10.1002/marc.200900660

Determining association constants from titration experiments in supramolecular chemistry
journal, January 2011


Enhancing exciton diffusion in porphyrin thin films using peripheral carboalkoxy groups to influence molecular assembly
journal, January 2016

  • Kaushal, Meesha; Ortiz, Angy L.; Kassel, Jennifer A.
  • Journal of Materials Chemistry C, Vol. 4, Issue 24
  • DOI: 10.1039/C6TC01741J

Synthesis, Optoelectronic Properties, Self-Association, and Base Pairing of Nucleobase-Functionalized Oligothiophenes
journal, September 2018

  • Fagnani, Danielle E.; Bou Zerdan, Raghida; Castellano, Ronald K.
  • The Journal of Organic Chemistry, Vol. 83, Issue 20
  • DOI: 10.1021/acs.joc.8b02138

Guanine–oligothiophene conjugates: liquid-crystalline properties, photoconductivities and ion-responsive emission of their nanoscale assemblies
journal, January 2018

  • Gan, Kian Ping; Yoshio, Masafumi; Sugihara, Yuki
  • Chemical Science, Vol. 9, Issue 3
  • DOI: 10.1039/C7SC03764C

Bio-complementary supramolecular polymers with effective self-healing functionality
journal, January 2015

  • Cheng, Chih-Chia; Chang, Feng-Chih; Dai, Shenghong A.
  • RSC Advances, Vol. 5, Issue 110
  • DOI: 10.1039/C5RA19708B