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Title: Synthesis of a soluble adenine-functionalized polythiophene through direct arylation polymerization and its fluorescence responsive behavior

Abstract

An adenine-functionalized polythiophene is synthesized via direct arylation polymerization using Boc-protection to overcome catalyst deactivation. The resulting copolymer is highly soluble and shows reversible fluorescence quenching.

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [1]
  1. Univ. of Tennessee, Knoxville, TN (United States)
  2. Univ. of Tennessee, Knoxville, TN (United States); Georgia Inst. of Technology, Atlanta, GA (United States)
  3. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Publication Date:
Research Org.:
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE; National Science Foundation (NSF)
OSTI Identifier:
1606026
Alternate Identifier(s):
OSTI ID: 1577005
Grant/Contract Number:  
AC05-00OR22725; 1512221
Resource Type:
Accepted Manuscript
Journal Name:
Polymer Chemistry
Additional Journal Information:
Journal Volume: 11; Journal Issue: 4; Journal ID: ISSN 1759-9954
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Sabury, Sina, Collier, Graham S., Ericson, Milton Nance, and Kilbey, S. Michael. Synthesis of a soluble adenine-functionalized polythiophene through direct arylation polymerization and its fluorescence responsive behavior. United States: N. p., 2019. Web. doi:10.1039/c9py01142k.
Sabury, Sina, Collier, Graham S., Ericson, Milton Nance, & Kilbey, S. Michael. Synthesis of a soluble adenine-functionalized polythiophene through direct arylation polymerization and its fluorescence responsive behavior. United States. https://doi.org/10.1039/c9py01142k
Sabury, Sina, Collier, Graham S., Ericson, Milton Nance, and Kilbey, S. Michael. Wed . "Synthesis of a soluble adenine-functionalized polythiophene through direct arylation polymerization and its fluorescence responsive behavior". United States. https://doi.org/10.1039/c9py01142k. https://www.osti.gov/servlets/purl/1606026.
@article{osti_1606026,
title = {Synthesis of a soluble adenine-functionalized polythiophene through direct arylation polymerization and its fluorescence responsive behavior},
author = {Sabury, Sina and Collier, Graham S. and Ericson, Milton Nance and Kilbey, S. Michael},
abstractNote = {An adenine-functionalized polythiophene is synthesized via direct arylation polymerization using Boc-protection to overcome catalyst deactivation. The resulting copolymer is highly soluble and shows reversible fluorescence quenching.},
doi = {10.1039/c9py01142k},
journal = {Polymer Chemistry},
number = 4,
volume = 11,
place = {United States},
year = {Wed Dec 04 00:00:00 EST 2019},
month = {Wed Dec 04 00:00:00 EST 2019}
}

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Cited by: 14 works
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Works referenced in this record:

Impact of π-conjugated gradient sequence copolymers on polymer blend morphology
journal, January 2013

  • Palermo, Edmund F.; van der Laan, Harry L.; McNeil, Anne J.
  • Polymer Chemistry, Vol. 4, Issue 17
  • DOI: 10.1039/c3py00601h

Multiplicity of metal ion binding patterns to nucleobases
journal, May 2000


Highly Efficient 2D-Conjugated Benzodithiophene-Based Photovoltaic Polymer with Linear Alkylthio Side Chain
journal, June 2014

  • Ye, Long; Zhang, Shaoqing; Zhao, Wenchao
  • Chemistry of Materials, Vol. 26, Issue 12
  • DOI: 10.1021/cm501513n

A highly sensitive and selective optical sensor for Pb2+ by using conjugated polymers and label-free oligonucleotides
journal, January 2013


8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands
journal, April 2009

  • Lambertucci, Catia; Antonini, Ippolito; Buccioni, Michela
  • Bioorganic & Medicinal Chemistry, Vol. 17, Issue 7
  • DOI: 10.1016/j.bmc.2009.02.030

Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines by a Combination of the Suzuki Cross-coupling, N-Arylation, and Direct C−H Arylation Reactions
journal, November 2008

  • Čerňa, Igor; Pohl, Radek; Klepetářová, Blanka
  • The Journal of Organic Chemistry, Vol. 73, Issue 22
  • DOI: 10.1021/jo8018126

New fluorescent chemosensors for metal ions in solution
journal, January 2012

  • Formica, Mauro; Fusi, Vieri; Giorgi, Luca
  • Coordination Chemistry Reviews, Vol. 256, Issue 1-2
  • DOI: 10.1016/j.ccr.2011.09.010

Direct (Hetero)Arylation: A New Tool for Polymer Chemists
journal, April 2013

  • Mercier, Lauren G.; Leclerc, Mario
  • Accounts of Chemical Research, Vol. 46, Issue 7
  • DOI: 10.1021/ar3003305

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

Analysis of the excited states of regioregular polythiophene P3HT
journal, January 2008

  • Cook, Steffan; Furube, Akihiro; Katoh, Ryuzi
  • Energy & Environmental Science, Vol. 1, Issue 2
  • DOI: 10.1039/b805643a

Nucleobases as supramolecular motifs
journal, January 2005

  • Sivakova, Sona; Rowan, Stuart J.
  • Chemical Society Reviews, Vol. 34, Issue 1
  • DOI: 10.1039/b304608g

A Simple Method to Generate Side-Chain Derivatives of Regioregular Polythiophene via the GRIM Metathesis and Post-polymerization Functionalization
journal, January 2003

  • Zhai, Lei; Pilston, Richard L.; Zaiger, Karen L.
  • Macromolecules, Vol. 36, Issue 1
  • DOI: 10.1021/ma0255884

Carbazole-based copolymers via direct arylation polymerization (DArP) for Suzuki-convergent polymer solar cell performance
journal, January 2017

  • Gobalasingham, Nemal S.; Ekiz, Seyma; Pankow, Robert M.
  • Polymer Chemistry, Vol. 8, Issue 30
  • DOI: 10.1039/C7PY00859G

Conducting Polymers in Solution—Progress Toward Processibility
journal, April 1999

  • Bhattacharya, Amit; De, Amitabha
  • Journal of Macromolecular Science, Part C: Polymer Reviews, Vol. 39, Issue 1
  • DOI: 10.1081/MC-100101416

Nucleobase Self-Assembly in Supramolecular Adhesives
journal, January 2012

  • Cheng, Shijing; Zhang, Mingqiang; Dixit, Ninad
  • Macromolecules, Vol. 45, Issue 2
  • DOI: 10.1021/ma202122r

Intramolecular Exciton Relaxation and Migration Dynamics in Poly(3-hexylthiophene)
journal, October 2007

  • Wells, Nathan P.; Boudouris, Bryan W.; Hillmyer, Marc A.
  • The Journal of Physical Chemistry C, Vol. 111, Issue 42
  • DOI: 10.1021/jp074657j

DNA-Templated Polymerization of Side-Chain-Functionalized Peptide Nucleic Acid Aldehydes
journal, April 2008

  • Kleiner, Ralph E.; Brudno, Yevgeny; Birnbaum, Michael E.
  • Journal of the American Chemical Society, Vol. 130, Issue 14
  • DOI: 10.1021/ja0753997

Effect of the Polymer Chain Arrangement on Exciton and Polaron Dynamics in P3HT and P3HT:PCBM Films
journal, March 2018

  • Dimitriev, Oleg P.; Blank, David A.; Ganser, Christian
  • The Journal of Physical Chemistry C, Vol. 122, Issue 30
  • DOI: 10.1021/acs.jpcc.8b05155

Fluorescent conjugated polymer molecular wire chemosensors for transition metal ion recognition and signaling
journal, February 2009

  • Fan, Li-Juan; Zhang, Yan; Murphy, Clifford B.
  • Coordination Chemistry Reviews, Vol. 253, Issue 3-4
  • DOI: 10.1016/j.ccr.2008.03.008

Thermal stability of P3HT and P3HT:PCBM blends in the molten state
journal, October 2013


Significant glass-transition-temperature increase through hydrogen-bonded copolymers
journal, August 2002

  • Kuo, Shiao-Wei; Xu, Hongyao; Huang, Chih-Feng
  • Journal of Polymer Science Part B: Polymer Physics, Vol. 40, Issue 19
  • DOI: 10.1002/polb.10292

Nucleobase-Functionalized Conjugated Polymer for Detection of Copper(II)
journal, June 2014

  • Xing, Chengfen; Yuan, Hongbo; Xu, Sichuan
  • ACS Applied Materials & Interfaces, Vol. 6, Issue 12
  • DOI: 10.1021/am502978w

Investigation of green and sustainable solvents for direct arylation polymerization (DArP)
journal, January 2018

  • Pankow, Robert M.; Ye, Liwei; Gobalasingham, Nemal S.
  • Polymer Chemistry, Vol. 9, Issue 28
  • DOI: 10.1039/C8PY00749G

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

Solvent Effect on the Absorption and Fluorescence Emission Spectra of Some Purine Derivatives: Spectrofluorometric Quantitative Studies
journal, May 2008

  • Hammud, Hassan H.; Bouhadir, Kamal H.; Masoud, Mamdouh S.
  • Journal of Solution Chemistry, Vol. 37, Issue 7
  • DOI: 10.1007/s10953-008-9289-8

Evidence of a Novel Side Chain Structure in Regioregular Poly(3-alkylthiophenes)
journal, January 1996

  • Prosa, T. J.; Winokur, M. J.; McCullough, R. D.
  • Macromolecules, Vol. 29, Issue 10
  • DOI: 10.1021/ma951510u

Direct (Hetero)arylation Polymerization: An Effective Route to 3,4-Propylenedioxythiophene-Based Polymers with Low Residual Metal Content
journal, September 2013

  • Estrada, Leandro A.; Deininger, James J.; Kamenov, George D.
  • ACS Macro Letters, Vol. 2, Issue 10
  • DOI: 10.1021/mz4003886

Molecular control of luminescence from poly(3-hexylthiophenes)
journal, August 1993


DNA biosensors based on water-soluble conjugated polymers
journal, January 2011


Multinuclear NMR studies of the interaction of metal ions with adenine-nucleotides
journal, November 2008


Supramolecular core–shell nanoparticles for photoconductive device applications
journal, June 2016


Effects of Alkylthio and Alkoxy Side Chains in Polymer Donor Materials for Organic Solar Cells
journal, January 2016

  • Cui, Chaohua; Wong, Wai-Yeung
  • Macromolecular Rapid Communications, Vol. 37, Issue 4
  • DOI: 10.1002/marc.201500620

Synthesis and Characterization of a Poly(1,3-dithienylisothianaphthene) Derivative for Bulk Heterojunction Photovoltaic Cells
journal, November 2001

  • Vangeneugden, D. L.; Vanderzande, D. J. M.; Salbeck, J.
  • The Journal of Physical Chemistry B, Vol. 105, Issue 45
  • DOI: 10.1021/jp013073t

Entrapment and Rigidification of Adenine by a Photo-Cross-Linked Thymine Network Leads to Fluorescent Polymer Nanoparticles
journal, February 2018


Hydrogen-Bonding-Directed Ordered Assembly of Carboxylated Poly(3-Alkylthiophene)s
journal, November 2017


Highly regioselective Pd/C-catalyzed direct arylation toward thiophene-based π-conjugated polymers
journal, January 2015

  • Hayashi, Shotaro; Kojima, Yoshihisa; Koizumi, Toshio
  • Polymer Chemistry, Vol. 6, Issue 6
  • DOI: 10.1039/C4PY01426J

Light-Emitting Polythiophenes
journal, October 2005

  • Perepichka, I. F.; Perepichka, D. F.; Meng, H.
  • Advanced Materials, Vol. 17, Issue 19
  • DOI: 10.1002/adma.200500461

Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices
journal, March 2009

  • Grimsdale, Andrew C.; Leok Chan, Khai; Martin, Rainer E.
  • Chemical Reviews, Vol. 109, Issue 3
  • DOI: 10.1021/cr000013v

Water-soluble fluorescent conjugated polymers and their interactions with biomacromolecules for sensitive biosensors
journal, January 2010

  • Feng, Xuli; Liu, Libing; Wang, Shu
  • Chemical Society Reviews, Vol. 39, Issue 7
  • DOI: 10.1039/b909065g

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

Fluorescent Conjugated Polyelectrolytes for Biomacromolecule Detection
journal, August 2008


Effect of electron-withdrawing side chain modifications on the optical properties of thiophene–quinoxaline acceptor based polymers
journal, February 2013


Functionalized conjugated polymers for sensing and molecular imprinting applications
journal, January 2019


X-ray structure and properties of a dinuclear palladium(II) complex [Pd2(μ-L)4] with four adenine-based bridges in a paddle wheel-like arrangement
journal, June 2010

  • Štarha, Pavel; Novotná, Radka; Trávníček, Zdeněk
  • Inorganic Chemistry Communications, Vol. 13, Issue 6
  • DOI: 10.1016/j.inoche.2010.04.001

Systematic Investigation of Side-Chain Branching Position Effect on Electron Carrier Mobility in Conjugated Polymers
journal, August 2014

  • Dou, Jin-Hu; Zheng, Yu-Qing; Lei, Ting
  • Advanced Functional Materials, Vol. 24, Issue 40
  • DOI: 10.1002/adfm.201401822

Probing structural consequences of N9-alkylation in silver-adenine frameworks
journal, January 2010

  • Mishra, Ashutosh Kumar; Prajapati, Rajneesh Kumar; Verma, Sandeep
  • Dalton Transactions, Vol. 39, Issue 42
  • DOI: 10.1039/c0dt00557f

Specific Recognition of Nucleobase-Functionalized Polythiophenes
journal, March 1998


Nucleobase-Containing Polymers: Structure, Synthesis, and Applications
journal, December 2017


Rhodamine B and rhodamine 101 as reference substances for fluorescence quantum yield measurements
journal, July 1980

  • Karstens, T.; Kobs, K.
  • The Journal of Physical Chemistry, Vol. 84, Issue 14
  • DOI: 10.1021/j100451a030

Adenine Tautomers:  Relative Stabilities, Ionization Energies, and Mismatch with Cytosine
journal, March 2006

  • Fonseca Guerra, C.; Bickelhaupt, F. M.; Saha, S.
  • The Journal of Physical Chemistry A, Vol. 110, Issue 11
  • DOI: 10.1021/jp057275r

Electroluminescent Conjugated Polymers—Seeing Polymers in a New Light
journal, March 1998


Tailoring the microstructure and charge transport in conjugated polymers by alkyl side-chain engineering
journal, January 2016

  • Fall, Sadiara; Biniek, Laure; Odarchenko, Yaroslav
  • Journal of Materials Chemistry C, Vol. 4, Issue 2
  • DOI: 10.1039/C5TC03000E

PNA/dsDNA Complexes:  Site Specific Binding and dsDNA Biosensor Applications
journal, July 2006

  • Baker, Erin Shammel; Hong, Janice W.; Gaylord, Brent S.
  • Journal of the American Chemical Society, Vol. 128, Issue 26
  • DOI: 10.1021/ja060069s

A Reversible and Highly Selective Fluorescent Sensor for Mercury(II) Using Poly(thiophene)s that Contain Thymine Moieties
journal, March 2006

  • Tang, Yanli; He, Fang; Yu, Minghui
  • Macromolecular Rapid Communications, Vol. 27, Issue 6
  • DOI: 10.1002/marc.200500837

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

Conjugated Polymers with Large Effective Stokes Shift: Benzobisdioxole-Based Poly(phenylene ethynylene)s
journal, December 2009

  • Dutta, Tanmoy; Woody, Kathy B.; Parkin, Sean R.
  • Journal of the American Chemical Society, Vol. 131, Issue 47
  • DOI: 10.1021/ja9068134

Influence of Branched Alkyl Ester-Labeled Side Chains on Specific Chain Arrangement and Charge-Transport Properties of Diketopyrrolopyrrole-Based Conjugated Polymers
journal, November 2018

  • Kim, Hyung Jong; Pei, Mingyuan; Ko, Joong Se
  • ACS Applied Materials & Interfaces, Vol. 10, Issue 47
  • DOI: 10.1021/acsami.8b13292

Optimization of direct arylation polymerization conditions for the synthesis of poly(3-hexylthiophene)
journal, March 2013

  • Rudenko, Andrey E.; Wiley, Calvin A.; Tannaci, John F.
  • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 51, Issue 12
  • DOI: 10.1002/pola.26655

Relevance, essentiality and toxicity of trace elements in human health
journal, August 2005


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


Improving Solar Cell Efficiency through Hydrogen Bonding: A Method for Tuning Active Layer Morphology
journal, February 2015

  • Aytun, Taner; Barreda, Leonel; Ruiz-Carretero, Amparo
  • Chemistry of Materials, Vol. 27, Issue 4
  • DOI: 10.1021/cm503915t

Effects of metal-ion binding on nucleobase pairing: stabilization, prevention and mismatch formation †
journal, January 1997

  • Lippert, Bernhard
  • Journal of the Chemical Society, Dalton Transactions, Issue 21
  • DOI: 10.1039/a702916k

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

The role of hydrogen bonding in bulk-heterojunction (BHJ) solar cells: A review
journal, August 2018


Direct (Hetero)arylation Polymerization: Trends and Perspectives
journal, July 2016

  • Bura, Thomas; Blaskovits, J. Terence; Leclerc, Mario
  • Journal of the American Chemical Society, Vol. 138, Issue 32
  • DOI: 10.1021/jacs.6b06237

Pyridine-terminated low gap π-conjugated oligomers: design, synthesis, and photophysical response to protonation and metalation
journal, January 2018

  • Weldeab, Asmerom O.; Li, Lei; Cekli, Seda
  • Organic Chemistry Frontiers, Vol. 5, Issue 21
  • DOI: 10.1039/C8QO00963E

The Effect of Metal Binding to the N7 Site of Purine Nucleotides on Their Structure, Energy, and Involvement in Base Pairing
journal, August 2000

  • Šponer, Jiří; Sabat, Michal; Gorb, Leonid
  • The Journal of Physical Chemistry B, Vol. 104, Issue 31
  • DOI: 10.1021/jp001711m

Amide-Containing Alkyl Chains in Conjugated Polymers: Effect on Self-Assembly and Electronic Properties
journal, February 2018


Static and dynamic fluorescence quenching experiments for the physical chemistry laboratory
journal, May 1992

  • Fraiji, Lee K.; Hayes, David M.; Werner, T. C.
  • Journal of Chemical Education, Vol. 69, Issue 5
  • DOI: 10.1021/ed069p424

8-(2-Furyl)adenine derivatives as A2A adenosine receptor ligands
journal, December 2013


Optimization of direct arylation polymerization (DArP) through the identification and control of defects in polymer structure
journal, June 2014

  • Rudenko, Andrey E.; Thompson, Barry C.
  • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 53, Issue 2
  • DOI: 10.1002/pola.27279

Significant Enhancement of Polymer Solar Cell Performance via Side-Chain Engineering and Simple Solvent Treatment
journal, July 2013

  • Wang, Yang; Liu, Ying; Chen, Shaojie
  • Chemistry of Materials, Vol. 25, Issue 15
  • DOI: 10.1021/cm401618h

Nucleobase–Fluorobenzene Interactions: Hydrogen Bonding Wins over π Stacking
journal, October 2007

  • Leist, Roman; Frey, Jann A.; Ottiger, Philipp
  • Angewandte Chemie, Vol. 119, Issue 39
  • DOI: 10.1002/ange.200701171

Photogeneration and Ultrafast Dynamics of Excitons and Charges in P3HT/PCBM Blends
journal, July 2009

  • Piris, Jorge; Dykstra, Tieneke E.; Bakulin, Artem A.
  • The Journal of Physical Chemistry C, Vol. 113, Issue 32
  • DOI: 10.1021/jp904229q

Homogeneous Fluorescence-Based DNA Detection with Water-Soluble Conjugated Polymers
journal, November 2004

  • Liu, Bin; Bazan, Guillermo C.
  • Chemistry of Materials, Vol. 16, Issue 23
  • DOI: 10.1021/cm049587x

Random Copolymers Allow Control of Crystallization and Microphase Separation in Fully Conjugated Block Copolymers
journal, October 2018


Nucleobases as Supramolecular Motifs
journal, May 2005


Nucleobase–Fluorobenzene Interactions: Hydrogen Bonding Wins over π Stacking
journal, October 2007

  • Leist, Roman; Frey, Jann A.; Ottiger, Philipp
  • Angewandte Chemie International Edition, Vol. 46, Issue 39
  • DOI: 10.1002/anie.200701171