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

Sabury, Sina; Collier, Graham S.; Ericson, Milton Nance; Kilbey, S. Michael

doi:10.1039/c9py01142k

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

Journal Article · 04 December 2019 · Polymer Chemistry

DOI: https://doi.org/10.1039/c9py01142k · OSTI ID:1606026

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Univ. of Tennessee, Knoxville, TN (United States)
Univ. of Tennessee, Knoxville, TN (United States); Georgia Inst. of Technology, Atlanta, GA (United States)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

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.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE; National Science Foundation (NSF)

Grant/Contract Number:: AC05-00OR22725; 1512221

OSTI ID:: 1606026

Alternate ID(s):: OSTI ID: 1577005

Journal Information:: Polymer Chemistry, Vol. 11, Issue 4; ISSN 1759-9954

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 14 works

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References (90)

Impact of π-conjugated gradient sequence copolymers on polymer blend morphology Palermo, Edmund F.; van der Laan, Harry L.; McNeil, Anne J. Polymer Chemistry, Vol. 4, Issue 17 https://doi.org/10.1039/c3py00601h	journal	January 2013
Multiplicity of metal ion binding patterns to nucleobases Lippert, Bernhard Coordination Chemistry Reviews, Vol. 200-202 https://doi.org/10.1016/S0010-8545(00)00260-5	journal	May 2000
Highly Efficient 2D-Conjugated Benzodithiophene-Based Photovoltaic Polymer with Linear Alkylthio Side Chain Ye, Long; Zhang, Shaoqing; Zhao, Wenchao Chemistry of Materials, Vol. 26, Issue 12 https://doi.org/10.1021/cm501513n	journal	June 2014
A highly sensitive and selective optical sensor for Pb2+ by using conjugated polymers and label-free oligonucleotides Lu, Yan; Li, Xiang; Wang, Gongke Biosensors and Bioelectronics, Vol. 39, Issue 1 https://doi.org/10.1016/j.bios.2012.07.045	journal	January 2013
8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands Lambertucci, Catia; Antonini, Ippolito; Buccioni, Michela Bioorganic & Medicinal Chemistry, Vol. 17, Issue 7 https://doi.org/10.1016/j.bmc.2009.02.030	journal	April 2009
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 Čerňa, Igor; Pohl, Radek; Klepetářová, Blanka The Journal of Organic Chemistry, Vol. 73, Issue 22 https://doi.org/10.1021/jo8018126	journal	November 2008
New fluorescent chemosensors for metal ions in solution Formica, Mauro; Fusi, Vieri; Giorgi, Luca Coordination Chemistry Reviews, Vol. 256, Issue 1-2 https://doi.org/10.1016/j.ccr.2011.09.010	journal	January 2012
Direct (Hetero)Arylation: A New Tool for Polymer Chemists Mercier, Lauren G.; Leclerc, Mario Accounts of Chemical Research, Vol. 46, Issue 7 https://doi.org/10.1021/ar3003305	journal	April 2013
Supramolecular polymeric micelles as high performance electrochemical materials Cheng, Chih-Chia; Chang, Feng-Chih; Ko, Fu-Hsiang Journal of Materials Chemistry C, Vol. 3, Issue 37 https://doi.org/10.1039/C5TC02130H	journal	January 2015
Nature of Impurities in .pi.-Conjugated Polymers Prepared by Ferric Chloride and Their Effect on the Electrical Properties of Metal-Insulator-Semiconductor Structures Abdou, Mohamed S. A.; Lu, Xiaotang; Xie, Zi W. Chemistry of Materials, Vol. 7, Issue 4 https://doi.org/10.1021/cm00052a006	journal	April 1995
Side Chain Engineering in Solution-Processable Conjugated Polymers Mei, Jianguo; Bao, Zhenan Chemistry of Materials, Vol. 26, Issue 1 https://doi.org/10.1021/cm4020805	journal	September 2013
Analysis of the excited states of regioregular polythiophene P3HT Cook, Steffan; Furube, Akihiro; Katoh, Ryuzi Energy & Environmental Science, Vol. 1, Issue 2 https://doi.org/10.1039/b805643a	journal	January 2008
Synthesis of conjugated polymers via an exclusive direct-arylation coupling reaction: a facile and straightforward way to synthesize thiophene-flanked benzothiadiazole derivatives and their copolymers Wang, Xiaochen; Wang, Kai; Wang, Mingfeng Polymer Chemistry, Vol. 6, Issue 10 https://doi.org/10.1039/C4PY01627K	journal	January 2015
Nucleobases as supramolecular motifs Sivakova, Sona; Rowan, Stuart J. Chemical Society Reviews, Vol. 34, Issue 1 https://doi.org/10.1039/b304608g	journal	January 2005
A Simple Method to Generate Side-Chain Derivatives of Regioregular Polythiophene via the GRIM Metathesis and Post-polymerization Functionalization Zhai, Lei; Pilston, Richard L.; Zaiger, Karen L. Macromolecules, Vol. 36, Issue 1 https://doi.org/10.1021/ma0255884	journal	January 2003
Carbazole-based copolymers via direct arylation polymerization (DArP) for Suzuki-convergent polymer solar cell performance Gobalasingham, Nemal S.; Ekiz, Seyma; Pankow, Robert M. Polymer Chemistry, Vol. 8, Issue 30 https://doi.org/10.1039/C7PY00859G	journal	January 2017
Conducting Polymers in Solution—Progress Toward Processibility Bhattacharya, Amit; De, Amitabha Journal of Macromolecular Science, Part C: Polymer Reviews, Vol. 39, Issue 1 https://doi.org/10.1081/MC-100101416	journal	April 1999
Nucleobase Self-Assembly in Supramolecular Adhesives Cheng, Shijing; Zhang, Mingqiang; Dixit, Ninad Macromolecules, Vol. 45, Issue 2 https://doi.org/10.1021/ma202122r	journal	January 2012
Intramolecular Exciton Relaxation and Migration Dynamics in Poly(3-hexylthiophene) Wells, Nathan P.; Boudouris, Bryan W.; Hillmyer, Marc A. The Journal of Physical Chemistry C, Vol. 111, Issue 42 https://doi.org/10.1021/jp074657j	journal	October 2007
DNA-Templated Polymerization of Side-Chain-Functionalized Peptide Nucleic Acid Aldehydes Kleiner, Ralph E.; Brudno, Yevgeny; Birnbaum, Michael E. Journal of the American Chemical Society, Vol. 130, Issue 14 https://doi.org/10.1021/ja0753997	journal	April 2008
Effect of the Polymer Chain Arrangement on Exciton and Polaron Dynamics in P3HT and P3HT:PCBM Films Dimitriev, Oleg P.; Blank, David A.; Ganser, Christian The Journal of Physical Chemistry C, Vol. 122, Issue 30 https://doi.org/10.1021/acs.jpcc.8b05155	journal	March 2018
Thioalkyl-Substituted Benzothiadiazole Acceptors: Copolymerization with Carbazole Affords Polymers with Large Stokes Shifts and High Solar Cell Voltages Casey, Abby; Ashraf, Raja Shahid; Fei, Zhuping Macromolecules, Vol. 47, Issue 7 https://doi.org/10.1021/ma5000943	journal	March 2014
A self-assembled triphenylamine-based fluorescent chemosensor for selective detection of Fe ³⁺ and Cu ²⁺ ions in aqueous solution Wenfeng, Li; Hengchang, Ma; con, Lu RSC Advances, Vol. 5, Issue 9 https://doi.org/10.1039/C4RA12025F	journal	January 2015
Fluorescent conjugated polymer molecular wire chemosensors for transition metal ion recognition and signaling Fan, Li-Juan; Zhang, Yan; Murphy, Clifford B. Coordination Chemistry Reviews, Vol. 253, Issue 3-4 https://doi.org/10.1016/j.ccr.2008.03.008	journal	February 2009
Thermal stability of P3HT and P3HT:PCBM blends in the molten state Rodrigues, Alexandre; Castro, M. Cidália R.; Farinha, Andreia S. F. Polymer Testing, Vol. 32, Issue 7 https://doi.org/10.1016/j.polymertesting.2013.07.008	journal	October 2013
Conjugated polymer/fullerene nanostructures through cooperative non-covalent interactions for organic solar cells Li, Fei; Dawson, Noel M.; Jiang, Ying-Bing Polymer, Vol. 76 https://doi.org/10.1016/j.polymer.2015.09.005	journal	October 2015
Significant glass-transition-temperature increase through hydrogen-bonded copolymers Kuo, Shiao-Wei; Xu, Hongyao; Huang, Chih-Feng Journal of Polymer Science Part B: Polymer Physics, Vol. 40, Issue 19 https://doi.org/10.1002/polb.10292	journal	August 2002
Nucleobase-Functionalized Conjugated Polymer for Detection of Copper(II) Xing, Chengfen; Yuan, Hongbo; Xu, Sichuan ACS Applied Materials & Interfaces, Vol. 6, Issue 12 https://doi.org/10.1021/am502978w	journal	June 2014
Investigation of green and sustainable solvents for direct arylation polymerization (DArP) Pankow, Robert M.; Ye, Liwei; Gobalasingham, Nemal S. Polymer Chemistry, Vol. 9, Issue 28 https://doi.org/10.1039/C8PY00749G	journal	January 2018
Linking design and properties of purine-based donor–acceptor chromophores as optoelectronic materials Collier, Graham S.; Brown, Lauren A.; Boone, Evan S. Journal of Materials Chemistry C, Vol. 5, Issue 27 https://doi.org/10.1039/C7TC01835E	journal	January 2017
Solvent Effect on the Absorption and Fluorescence Emission Spectra of Some Purine Derivatives: Spectrofluorometric Quantitative Studies Hammud, Hassan H.; Bouhadir, Kamal H.; Masoud, Mamdouh S. Journal of Solution Chemistry, Vol. 37, Issue 7 https://doi.org/10.1007/s10953-008-9289-8	journal	May 2008
Evidence of a Novel Side Chain Structure in Regioregular Poly(3-alkylthiophenes) Prosa, T. J.; Winokur, M. J.; McCullough, R. D. Macromolecules, Vol. 29, Issue 10 https://doi.org/10.1021/ma951510u	journal	January 1996
Direct (Hetero)arylation Polymerization: An Effective Route to 3,4-Propylenedioxythiophene-Based Polymers with Low Residual Metal Content Estrada, Leandro A.; Deininger, James J.; Kamenov, George D. ACS Macro Letters, Vol. 2, Issue 10 https://doi.org/10.1021/mz4003886	journal	September 2013
Molecular control of luminescence from poly(3-hexylthiophenes) Xu, Bai; Holdcroft, Steven Macromolecules, Vol. 26, Issue 17 https://doi.org/10.1021/ma00069a009	journal	August 1993
DNA biosensors based on water-soluble conjugated polymers Liu, Xingfen; Fan, Quli; Huang, Wei Biosensors and Bioelectronics, Vol. 26, Issue 5 https://doi.org/10.1016/j.bios.2010.09.025	journal	January 2011
Multinuclear NMR studies of the interaction of metal ions with adenine-nucleotides Szabó, Zoltán Coordination Chemistry Reviews, Vol. 252, Issue 21-22 https://doi.org/10.1016/j.ccr.2008.03.002	journal	November 2008
Supramolecular core–shell nanoparticles for photoconductive device applications Cheng, Chih-Chia; Chen, Jem-Kun; Shieh, Yeong-Tarng Nanotechnology, Vol. 27, Issue 32 https://doi.org/10.1088/0957-4484/27/32/32LT01	journal	June 2016
Effects of Alkylthio and Alkoxy Side Chains in Polymer Donor Materials for Organic Solar Cells Cui, Chaohua; Wong, Wai-Yeung Macromolecular Rapid Communications, Vol. 37, Issue 4 https://doi.org/10.1002/marc.201500620	journal	January 2016
Synthesis and Characterization of a Poly(1,3-dithienylisothianaphthene) Derivative for Bulk Heterojunction Photovoltaic Cells Vangeneugden, D. L.; Vanderzande, D. J. M.; Salbeck, J. The Journal of Physical Chemistry B, Vol. 105, Issue 45 https://doi.org/10.1021/jp013073t	journal	November 2001
Entrapment and Rigidification of Adenine by a Photo-Cross-Linked Thymine Network Leads to Fluorescent Polymer Nanoparticles Hua, Zan; Wilks, Thomas R.; Keogh, Robert Chemistry of Materials, Vol. 30, Issue 4 https://doi.org/10.1021/acs.chemmater.7b05206	journal	February 2018
Hydrogen-Bonding-Directed Ordered Assembly of Carboxylated Poly(3-Alkylthiophene)s Bilger, David W.; Figueroa, Jose A.; Redeker, Neil D. ACS Omega, Vol. 2, Issue 11 https://doi.org/10.1021/acsomega.7b01361	journal	November 2017
Highly regioselective Pd/C-catalyzed direct arylation toward thiophene-based π-conjugated polymers Hayashi, Shotaro; Kojima, Yoshihisa; Koizumi, Toshio Polymer Chemistry, Vol. 6, Issue 6 https://doi.org/10.1039/C4PY01426J	journal	January 2015
Light-Emitting Polythiophenes Perepichka, I. F.; Perepichka, D. F.; Meng, H. Advanced Materials, Vol. 17, Issue 19 https://doi.org/10.1002/adma.200500461	journal	October 2005
Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices Grimsdale, Andrew C.; Leok Chan, Khai; Martin, Rainer E. Chemical Reviews, Vol. 109, Issue 3 https://doi.org/10.1021/cr000013v	journal	March 2009
Water-soluble fluorescent conjugated polymers and their interactions with biomacromolecules for sensitive biosensors Feng, Xuli; Liu, Libing; Wang, Shu Chemical Society Reviews, Vol. 39, Issue 7 https://doi.org/10.1039/b909065g	journal	January 2010
Significant Improvement of Semiconducting Performance of the Diketopyrrolopyrrole–Quaterthiophene Conjugated Polymer through Side-Chain Engineering via Hydrogen-Bonding Yao, Jingjing; Yu, Chenmin; Liu, Zitong Journal of the American Chemical Society, Vol. 138, Issue 1 https://doi.org/10.1021/jacs.5b09737	journal	December 2015
New bioinspired hole injection/transport materials for highly efficient solution-processed phosphorescent organic light-emitting diodes Cheng, Chih-Chia; Chu, Yu-Lin; Chang, Feng-Chih Nano Energy, Vol. 13 https://doi.org/10.1016/j.nanoen.2015.02.010	journal	April 2015
Fluorescent Conjugated Polyelectrolytes for Biomacromolecule Detection Feng, Fude; He, Fang; An, Lingling Advanced Materials, Vol. 20, Issue 15 https://doi.org/10.1002/adma.200800624	journal	August 2008
Effect of electron-withdrawing side chain modifications on the optical properties of thiophene–quinoxaline acceptor based polymers Kroon, Renee; Lundin, Angelica; Lindqvist, Camilla Polymer, Vol. 54, Issue 4 https://doi.org/10.1016/j.polymer.2013.01.003	journal	February 2013
Functionalized conjugated polymers for sensing and molecular imprinting applications Anantha-Iyengar, Gopalan; Shanmugasundaram, Komathi; Nallal, Muthuchamy Progress in Polymer Science, Vol. 88 https://doi.org/10.1016/j.progpolymsci.2018.08.001	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 Štarha, Pavel; Novotná, Radka; Trávníček, Zdeněk Inorganic Chemistry Communications, Vol. 13, Issue 6 https://doi.org/10.1016/j.inoche.2010.04.001	journal	June 2010
Systematic Investigation of Side-Chain Branching Position Effect on Electron Carrier Mobility in Conjugated Polymers Dou, Jin-Hu; Zheng, Yu-Qing; Lei, Ting Advanced Functional Materials, Vol. 24, Issue 40 https://doi.org/10.1002/adfm.201401822	journal	August 2014
Probing structural consequences of N9-alkylation in silver-adenine frameworks Mishra, Ashutosh Kumar; Prajapati, Rajneesh Kumar; Verma, Sandeep Dalton Transactions, Vol. 39, Issue 42 https://doi.org/10.1039/c0dt00557f	journal	January 2010
Specific Recognition of Nucleobase-Functionalized Polythiophenes Bäuerle, Peter; Emge, Andreas Advanced Materials, Vol. 10, Issue 4 https://doi.org/10.1002/(SICI)1521-4095(199803)10:4<324::AID-ADMA324>3.0.CO;2-E	journal	March 1998
Nucleobase-Containing Polymers: Structure, Synthesis, and Applications Yang, Haitao; Xi, Weixian Polymers, Vol. 9, Issue 12 https://doi.org/10.3390/polym9120666	journal	December 2017
Rhodamine B and rhodamine 101 as reference substances for fluorescence quantum yield measurements Karstens, T.; Kobs, K. The Journal of Physical Chemistry, Vol. 84, Issue 14 https://doi.org/10.1021/j100451a030	journal	July 1980
Adenine Tautomers: Relative Stabilities, Ionization Energies, and Mismatch with Cytosine Fonseca Guerra, C.; Bickelhaupt, F. M.; Saha, S. The Journal of Physical Chemistry A, Vol. 110, Issue 11 https://doi.org/10.1021/jp057275r	journal	March 2006
Electroluminescent Conjugated Polymers—Seeing Polymers in a New Light Kraft, Arno; Grimsdale, Andrew C.; Holmes, Andrew B. Angewandte Chemie International Edition, Vol. 37, Issue 4 https://doi.org/10.1002/(SICI)1521-3773(19980302)37:4<402::AID-ANIE402>3.0.CO;2-9	journal	March 1998
Tailoring the microstructure and charge transport in conjugated polymers by alkyl side-chain engineering Fall, Sadiara; Biniek, Laure; Odarchenko, Yaroslav Journal of Materials Chemistry C, Vol. 4, Issue 2 https://doi.org/10.1039/C5TC03000E	journal	January 2016
PNA/dsDNA Complexes: Site Specific Binding and dsDNA Biosensor Applications Baker, Erin Shammel; Hong, Janice W.; Gaylord, Brent S. Journal of the American Chemical Society, Vol. 128, Issue 26 https://doi.org/10.1021/ja060069s	journal	July 2006
A Reversible and Highly Selective Fluorescent Sensor for Mercury(II) Using Poly(thiophene)s that Contain Thymine Moieties Tang, Yanli; He, Fang; Yu, Minghui Macromolecular Rapid Communications, Vol. 27, Issue 6 https://doi.org/10.1002/marc.200500837	journal	March 2006
Bioinspired hole-conducting polymers for application in organic light-emitting diodes Cheng, Chih-Chia; Chu, Yu-Lin; Huang, Pei-Hsiu Journal of Materials Chemistry, Vol. 22, Issue 35 https://doi.org/10.1039/c2jm32665e	journal	January 2012
Conjugated Polymers with Large Effective Stokes Shift: Benzobisdioxole-Based Poly(phenylene ethynylene)s Dutta, Tanmoy; Woody, Kathy B.; Parkin, Sean R. Journal of the American Chemical Society, Vol. 131, Issue 47 https://doi.org/10.1021/ja9068134	journal	December 2009
An ultrasensitive label-free biosensor for assaying of sequence-specific DNA-binding protein based on amplifying fluorescent conjugated polymer Liu, Xingfen; Ouyang, Lan; Cai, Xiaohui Biosensors and Bioelectronics, Vol. 41 https://doi.org/10.1016/j.bios.2012.08.027	journal	March 2013
Influence of Branched Alkyl Ester-Labeled Side Chains on Specific Chain Arrangement and Charge-Transport Properties of Diketopyrrolopyrrole-Based Conjugated Polymers Kim, Hyung Jong; Pei, Mingyuan; Ko, Joong Se ACS Applied Materials & Interfaces, Vol. 10, Issue 47 https://doi.org/10.1021/acsami.8b13292	journal	November 2018
Optimization of direct arylation polymerization conditions for the synthesis of poly(3-hexylthiophene) Rudenko, Andrey E.; Wiley, Calvin A.; Tannaci, John F. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 51, Issue 12 https://doi.org/10.1002/pola.26655	journal	March 2013
Relevance, essentiality and toxicity of trace elements in human health Fraga, Cesar G. Molecular Aspects of Medicine, Vol. 26, Issue 4-5 https://doi.org/10.1016/j.mam.2005.07.013	journal	August 2005
Synthesis of Main Chain Purine-Based Copolymers and Effects of Monomer Design on Thermal and Optical Properties Collier, Graham S.; Brown, Lauren A.; Boone, Evan S. ACS Macro Letters, Vol. 5, Issue 6 https://doi.org/10.1021/acsmacrolett.6b00275	journal	May 2016
Improving Solar Cell Efficiency through Hydrogen Bonding: A Method for Tuning Active Layer Morphology Aytun, Taner; Barreda, Leonel; Ruiz-Carretero, Amparo Chemistry of Materials, Vol. 27, Issue 4 https://doi.org/10.1021/cm503915t	journal	February 2015
Effects of metal-ion binding on nucleobase pairing: stabilization, prevention and mismatch formation † Lippert, Bernhard Journal of the Chemical Society, Dalton Transactions, Issue 21 https://doi.org/10.1039/a702916k	journal	January 1997
Record High Hole Mobility in Polymer Semiconductors via Side-Chain Engineering Kang, Il; Yun, Hui-Jun; Chung, Dae Sung Journal of the American Chemical Society, Vol. 135, Issue 40 https://doi.org/10.1021/ja405112s	journal	September 2013
Fine-tuning blend morphology via alkylthio side chain engineering towards high performance non-fullerene polymer solar cells Li, Ling; Feng, Liuliu; Yuan, Jun Chemical Physics Letters, Vol. 696 https://doi.org/10.1016/j.cplett.2018.02.033	journal	March 2018
The role of hydrogen bonding in bulk-heterojunction (BHJ) solar cells: A review Xiao, Zeyun; Duan, Tainan; Chen, Haiyan Solar Energy Materials and Solar Cells, Vol. 182 https://doi.org/10.1016/j.solmat.2018.03.013	journal	August 2018
Direct (Hetero)arylation Polymerization: Trends and Perspectives Bura, Thomas; Blaskovits, J. Terence; Leclerc, Mario Journal of the American Chemical Society, Vol. 138, Issue 32 https://doi.org/10.1021/jacs.6b06237	journal	July 2016
Pyridine-terminated low gap π-conjugated oligomers: design, synthesis, and photophysical response to protonation and metalation Weldeab, Asmerom O.; Li, Lei; Cekli, Seda Organic Chemistry Frontiers, Vol. 5, Issue 21 https://doi.org/10.1039/C8QO00963E	journal	January 2018
The Effect of Metal Binding to the N7 Site of Purine Nucleotides on Their Structure, Energy, and Involvement in Base Pairing Šponer, Jiří; Sabat, Michal; Gorb, Leonid The Journal of Physical Chemistry B, Vol. 104, Issue 31 https://doi.org/10.1021/jp001711m	journal	August 2000
Amide-Containing Alkyl Chains in Conjugated Polymers: Effect on Self-Assembly and Electronic Properties Ocheje, Michael U.; Charron, Brynn P.; Cheng, Yu-Hsuan Macromolecules, Vol. 51, Issue 4 https://doi.org/10.1021/acs.macromol.7b02393	journal	February 2018
Effect of Spacer Length and Solvent on the Concentration-Driven Aggregation of Cationic Hydrogen-Bonding Donor Polythiophenes Domínguez, S. E.; Cangiotti, M.; Fattori, A. Langmuir, Vol. 34, Issue 25 https://doi.org/10.1021/acs.langmuir.8b00808	journal	May 2018
Conjugated Semiconducting Polymer with Thymine Groups in the Side Chains: Charge Mobility Enhancement and Application for Selective Field-Effect Transistor Sensors toward CO and H ₂ S Yang, Yizhou; Liu, Zitong; Chen, Liangliang Chemistry of Materials, Vol. 31, Issue 5 https://doi.org/10.1021/acs.chemmater.9b00106	journal	February 2019
Static and dynamic fluorescence quenching experiments for the physical chemistry laboratory Fraiji, Lee K.; Hayes, David M.; Werner, T. C. Journal of Chemical Education, Vol. 69, Issue 5 https://doi.org/10.1021/ed069p424	journal	May 1992
8-(2-Furyl)adenine derivatives as A2A adenosine receptor ligands Dal Ben, Diego; Buccioni, Michela; Lambertucci, Catia European Journal of Medicinal Chemistry, Vol. 70 https://doi.org/10.1016/j.ejmech.2013.10.006	journal	December 2013
Optimization of direct arylation polymerization (DArP) through the identification and control of defects in polymer structure Rudenko, Andrey E.; Thompson, Barry C. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 53, Issue 2 https://doi.org/10.1002/pola.27279	journal	June 2014
Significant Enhancement of Polymer Solar Cell Performance via Side-Chain Engineering and Simple Solvent Treatment Wang, Yang; Liu, Ying; Chen, Shaojie Chemistry of Materials, Vol. 25, Issue 15 https://doi.org/10.1021/cm401618h	journal	July 2013
Nucleobase–Fluorobenzene Interactions: Hydrogen Bonding Wins over π Stacking Leist, Roman; Frey, Jann A.; Ottiger, Philipp Angewandte Chemie, Vol. 119, Issue 39 https://doi.org/10.1002/ange.200701171	journal	October 2007
Photogeneration and Ultrafast Dynamics of Excitons and Charges in P3HT/PCBM Blends Piris, Jorge; Dykstra, Tieneke E.; Bakulin, Artem A. The Journal of Physical Chemistry C, Vol. 113, Issue 32 https://doi.org/10.1021/jp904229q	journal	July 2009
Homogeneous Fluorescence-Based DNA Detection with Water-Soluble Conjugated Polymers Liu, Bin; Bazan, Guillermo C. Chemistry of Materials, Vol. 16, Issue 23 https://doi.org/10.1021/cm049587x	journal	November 2004
Crystalline Random Conjugated Copolymers with Multiple Side Chains: Tunable Intermolecular Interactions and Enhanced Charge Transport and Photovoltaic Properties Wu, Pei-Tzu; Ren, Guoqiang; Jenekhe, Samson A. Macromolecules, Vol. 43, Issue 7 https://doi.org/10.1021/ma100006x	journal	April 2010
Random Copolymers Allow Control of Crystallization and Microphase Separation in Fully Conjugated Block Copolymers Lee, Youngmin; Aplan, Melissa P.; Seibers, Zach D. Macromolecules, Vol. 51, Issue 21 https://doi.org/10.1021/acs.macromol.8b01859	journal	October 2018
Nucleobases as Supramolecular Motifs Sivakova, Sona; Rowan, Stuart J. ChemInform, Vol. 36, Issue 18 https://doi.org/10.1002/chin.200518233	journal	May 2005
Nucleobase–Fluorobenzene Interactions: Hydrogen Bonding Wins over π Stacking Leist, Roman; Frey, Jann A.; Ottiger, Philipp Angewandte Chemie International Edition, Vol. 46, Issue 39 https://doi.org/10.1002/anie.200701171	journal	October 2007