Highly fluorescent purine-containing conjugated copolymers with tailored optoelectronic properties

O'Connell, C. Elizabeth; Sabury, Sina; Jenkins, J. Elias; Collier, Graham S.; Sumpter, Bobby G.; Long, Brian K.; Kilbey, II, S. Michael

doi:10.1039/d2py00545j

Highly fluorescent purine-containing conjugated copolymers with tailored optoelectronic properties

Journal Article · Fri Aug 12 00:00:00 EDT 2022 · Polymer Chemistry

DOI:https://doi.org/10.1039/d2py00545j· OSTI ID:1883818

O'Connell, C. Elizabeth ^[1]; ^[1]; Jenkins, J. Elias ^[1]; ^[2]; ^[3]; ^[1]; ^[1]

Univ. of Tennessee, Knoxville, TN (United States)
Kennesaw State University, GA (United States)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Conjugated copolymers containing electron donor and acceptor units in their main chain have emerged as promising materials for organic electronic devices due to their tunable optoelectronic properties. In this work, we describe the use of direct arylation polymerization to create a series of fully π-conjugated copolymers containing the highly tailorable purine scaffold as a key design element. To create efficient coupling sites, dihalopurines are flanked by alkylthiophenes to create a monomer that is readily copolymerized with a variety of conjugated comonomers, ranging from electron-donating 3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine to electron-accepting 4,7-bis(5-bromo-3-hexylthiophen-2-yl)benzo[c][1,2,5]thiadiazole. The comonomer choice and electronic nature of the purine scaffold allow the photophysical properties of the purine-containing copolymers to be widely varied, with optical bandgaps ranging from 1.96–2.46 eV, and photoluminescent quantum yields as high as Φ = 0.61. Frontier orbital energy levels determined for the various copolymers using density functional theory tight binding calculations track with experimental results, and the geometric structures of the alkylthiophene-flanked purine monomer and its copolymer are found to be nearly planar. The utility of direct arylation polymerization and intrinsic tailorability of the purine scaffold highlight the potential of these fully conjugated polymers to establish structure–property relationships based on connectivity pattern and comonomer type, which may broadly inform efforts to advance purine-containing conjugated copolymers for various applications.

View Accepted Manuscript (DOE)

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

Sponsoring Organization:: National Science Foundation (NSF); USDOE; USDOE Office of Energy Efficiency and Renewable Energy (EERE); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC05-00OR22725; EE0009177

OSTI ID:: 1883818

Alternate ID(s):: OSTI ID: 1881371

Journal Information:: Polymer Chemistry, Journal Name: Polymer Chemistry Journal Issue: 34 Vol. 13; ISSN 1759-9954

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (80)

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
Optical Bandgaps of π-Conjugated Organic Materials at the Polymer Limit: Experiment and Theory Gierschner, J.; Cornil, J.; Egelhaaf, H. -J. Advanced Materials, Vol. 19, Issue 2 https://doi.org/10.1002/adma.200600277	journal	January 2007
Relating Frontier Orbital Energies from Voltammetry and Photoelectron Spectroscopy to the Open-Circuit Voltage of Organic Solar Cells Willems, Robin E. M.; Weijtens, Christ H. L.; de Vries, Xander Advanced Energy Materials, Vol. 9, Issue 10 https://doi.org/10.1002/aenm.201803677	journal	January 2019
Theoretical Studies on the Intermolecular Interactions of Potentially Primordial Base-Pair Analogues Šponer, Judit E.; Vázquez-Mayagoitia, Álvaro; Sumpter, Bobby G. Chemistry - A European Journal, Vol. 16, Issue 10 https://doi.org/10.1002/chem.200902068	journal	March 2010
Syntheses of Purines Bearing Carbon Substituents in Positions 2, 6 or 8 by Metal‐ or Organometal‐Mediated C−C Bond‐Forming Reactions Hocek, Michal European Journal of Organic Chemistry, Vol. 2003, Issue 2 https://doi.org/10.1002/ejoc.200390025	journal	December 2002
Synthesis and properties of fluorene-based fluorinated polymers Kameshima, Hisamitsu; Nemoto, Nobukatsu; Endo, Takeshi Journal of Polymer Science Part A: Polymer Chemistry, Vol. 39, Issue 18 https://doi.org/10.1002/pola.1296	journal	January 2001
Synthesis and electroluminescent properties of polyfluorene-based conjugated polymers containing bipolar groups: Conjugated polymers Containing Bipolar Groups Huang, Sheng-Tung; Liaw, Der-Jang; Hsieh, Li-Ga Journal of Polymer Science Part A: Polymer Chemistry, Vol. 47, Issue 22 https://doi.org/10.1002/pola.23667	journal	October 2009
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
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
Synthesis and characterization of alternating fluorene–thiophene copolymers bearing ethylene glycol side-chains Ziegler, Elisabeth; Pein, Andreas; Fischereder, Achim Monatshefte für Chemie - Chemical Monthly, Vol. 142, Issue 2 https://doi.org/10.1007/s00706-010-0440-z	journal	January 2011
Regiochemistry in Stille couplings of 2,6-dihalopurines Langli, Geir; Gundersen, Lise-Lotte; Rise, Frode Tetrahedron, Vol. 52, Issue 15 https://doi.org/10.1016/0040-4020(96)00199-8	journal	April 1996
NWChem: A comprehensive and scalable open-source solution for large scale molecular simulations Valiev, M.; Bylaska, E. J.; Govind, N. Computer Physics Communications, Vol. 181, Issue 9, p. 1477-1489 https://doi.org/10.1016/j.cpc.2010.04.018	journal	September 2010
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
Direct arylation polymerization: A guide to optimal conditions for effective conjugated polymers Gobalasingham, Nemal S.; Thompson, Barry C. Progress in Polymer Science, Vol. 83 https://doi.org/10.1016/j.progpolymsci.2018.06.002	journal	August 2018
Synthesis and photoluminescence properties of π-extended fluorene derivatives: the first example of a fluorescent solvatochromic nitro-group-containing dye with a high fluorescence quantum yield Kotaka, Hidehiro; Konishi, Gen-ichi; Mizuno, Kazuhiko Tetrahedron Letters, Vol. 51, Issue 1 https://doi.org/10.1016/j.tetlet.2009.10.118	journal	January 2010
Electrochromic Polymers Processed from Environmentally Benign Solvents Collier, Graham S.; Pelse, Ian; Österholm, Anna M. Chemistry of Materials, Vol. 30, Issue 15 https://doi.org/10.1021/acs.chemmater.8b01765	journal	July 2018
Disentangling Redox Properties and Capacitance in Solution-Processed Conjugated Polymers Österholm, Anna M.; Ponder, James F.; De Keersmaecker, Michel Chemistry of Materials, Vol. 31, Issue 8 https://doi.org/10.1021/acs.chemmater.9b00528	journal	March 2019
Direct (Hetero)arylation Polymerization: Simplicity for Conjugated Polymer Synthesis Pouliot, Jean-Rémi; Grenier, François; Blaskovits, J. Terence Chemical Reviews, Vol. 116, Issue 22 https://doi.org/10.1021/acs.chemrev.6b00498	journal	October 2016
Synthesis, Optoelectronic Properties, Self-Association, and Base Pairing of Nucleobase-Functionalized Oligothiophenes Fagnani, Danielle E.; Bou Zerdan, Raghida; Castellano, Ronald K. The Journal of Organic Chemistry, Vol. 83, Issue 20 https://doi.org/10.1021/acs.joc.8b02138	journal	September 2018
Two-Photon Emissive Dyes Based on Push–Pull Purines Derivatives: Toward the Development of New Photoluminescence Bioprobes Zucolotto Cocca, Leandro H.; Abegão, Luis M. G.; Sciuti, Lucas F. The Journal of Physical Chemistry C, Vol. 124, Issue 23 https://doi.org/10.1021/acs.jpcc.0c01859	journal	May 2020
Effects of Cross-Conjugation on the Optical Absorption and Frontier Orbital Levels of Donor–Acceptor Polymers van Pruissen, Gijs W. P.; Brebels, Jeroen; Hendriks, Koen H. Macromolecules, Vol. 48, Issue 8 https://doi.org/10.1021/acs.macromol.5b00046	journal	April 2015
Systematic Tuning of 2,1,3-Benzothiadiazole Acceptor Strength by Monofunctionalization with Alkylamine, Thioalkyl, or Alkoxy Groups in Carbazole Donor–Acceptor Polymers Creamer, Adam; Casey, Abby; Marsh, Adam V. Macromolecules, Vol. 50, Issue 7 https://doi.org/10.1021/acs.macromol.7b00235	journal	March 2017
Nucleobase-Functionalized Poly(alkylthiophene)s: One-Pot, Sequential Direct Arylation Polymerization and Deprotection, and Surface Modification for Oil–Water Separations Sabury, Sina; LaRiviere, Ben; Ericson, M. Nance ACS Applied Polymer Materials, Vol. 3, Issue 2 https://doi.org/10.1021/acsapm.0c01281	journal	January 2021
Near-Infrared Polymer Dots with Aggregation-Induced Emission for Tumor Imaging Zhang, Zhe; Chen, Dandan; Liu, Zhihe ACS Applied Polymer Materials, Vol. 2, Issue 1 https://doi.org/10.1021/acsapm.9b00977	journal	December 2019
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
Photophysical and Electrical Properties of Highly Luminescent 2/6-Triazolyl-Substituted Push–Pull Purines Sebris, Armands; Novosjolova, Irina; Traskovskis, Kaspars ACS Omega, Vol. 7, Issue 6 https://doi.org/10.1021/acsomega.1c06359	journal	February 2022
Oligothiophene Semiconductors: Synthesis, Characterization, and Applications for Organic Devices Zhang, Lei; Colella, Nicholas S.; Cherniawski, Benjamin P. ACS Applied Materials & Interfaces, Vol. 6, Issue 8 https://doi.org/10.1021/am4060468	journal	March 2014
Fluorinated Benzothiadiazole (BT) Groups as a Powerful Unit for High-Performance Electron-Transporting Polymers Lee, Junghoon; Jang, Moonjeong; Lee, Sang Myeon ACS Applied Materials & Interfaces, Vol. 6, Issue 22 https://doi.org/10.1021/am505925w	journal	October 2014
Blue-Violet Electroluminescence from a Highly Fluorescent Purine Yang, Yixing; Cohn, Pamela; Dyer, Aubrey L. Chemistry of Materials, Vol. 22, Issue 12 https://doi.org/10.1021/cm100407n	journal	June 2010
Structure-Performance Correlations in Spray-Processable Green Dioxythiophene-Benzothiadiazole Donor–Acceptor Polymer Electrochromes Beaujuge, Pierre M.; Vasilyeva, Svetlana V.; Liu, David Y. Chemistry of Materials, Vol. 24, Issue 2 https://doi.org/10.1021/cm202117d	journal	January 2012
Synthesis and UV−Visible Properties of Soluble Regioregular Oligo(3-octylthiophenes), Monomer to Hexamer Bidan, G.; De Nicola, A.; Enée, V. Chemistry of Materials, Vol. 10, Issue 4 https://doi.org/10.1021/cm9706558	journal	April 1998
Parametrization and Benchmark of DFTB3 for Organic Molecules Gaus, Michael; Goez, Albrecht; Elstner, Marcus Journal of Chemical Theory and Computation, Vol. 9, Issue 1 https://doi.org/10.1021/ct300849w	journal	November 2012
Energy Gap Law for Nonradiative and Radiative Charge Transfer in Isolated and in Solvated Supermolecules Bixon, M.; Jortner, Joshua; Cortes, J. The Journal of Physical Chemistry, Vol. 98, Issue 30 https://doi.org/10.1021/j100081a010	journal	July 1994
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
The first regioregular head-to-tail poly(3-hexylthiophene-2,5-diyl) and a regiorandom isopolymer: nickel versus palladium catalysis of 2(5)-bromo-5(2)-(bromozincio)-3-hexylthiophene polymerization Chen, Tian An; Rieke, Reuben D. Journal of the American Chemical Society, Vol. 114, Issue 25 https://doi.org/10.1021/ja00051a066	journal	December 1992
Synthesis and Spectroscopic Properties of a Series of β-Blocked Long Oligothiophenes up to the 96-mer: Revaluation of Effective Conjugation Length Izumi, Tsuyoshi; Kobashi, Seiji; Takimiya, Kazuo Journal of the American Chemical Society, Vol. 125, Issue 18 https://doi.org/10.1021/ja034333i	journal	May 2003
Soluble Narrow Band Gap and Blue Propylenedioxythiophene-Cyanovinylene Polymers as Multifunctional Materials for Photovoltaic and Electrochromic Applications Thompson, Barry C.; Kim, Young-Gi; McCarley, Tracy D. Journal of the American Chemical Society, Vol. 128, Issue 39 https://doi.org/10.1021/ja061274a	journal	October 2006
Synthesis, Electronic Structure, Molecular Packing/Morphology Evolution, and Carrier Mobilities of Pure Oligo-/Poly(alkylthiophenes) Zhang, Lei; Colella, Nicholas S.; Liu, Feng Journal of the American Chemical Society, Vol. 135, Issue 2 https://doi.org/10.1021/ja3104796	journal	December 2012
Discrete Photopatternable π-Conjugated Oligomers for Electrochromic Devices Nielsen, Christian B.; Angerhofer, Alex; Abboud, Khalil A. Journal of the American Chemical Society, Vol. 130, Issue 30 https://doi.org/10.1021/ja7112273	journal	July 2008
Synthesis, Optical Properties, and Electronic Structures of Nucleobase-Containing π-Conjugated Oligomers Bou Zerdan, Raghida; Cohn, Pamela; Puodziukynaite, Egle The Journal of Organic Chemistry, Vol. 80, Issue 3 https://doi.org/10.1021/jo502773g	journal	January 2015
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
Size-Expanded DNA Bases: An Ab Initio Study of Their Structural and Electronic Properties Fuentes-Cabrera, Miguel; Sumpter, Bobby G.; Wells, Jack C. The Journal of Physical Chemistry B, Vol. 109, Issue 44 https://doi.org/10.1021/jp055210i	journal	November 2005
Size-Expanded yDNA Bases: An Ab Initio Study Fuentes-Cabrera, M.; Sumpter, Bobby G.; Lipkowski, Pawel The Journal of Physical Chemistry B, Vol. 110, Issue 12 https://doi.org/10.1021/jp057356n	journal	March 2006
What Determines Inhomogeneous Broadening of Electronic Transitions in Conjugated Polymers? Hoffmann, Sebastian T.; Bässler, Heinz; Köhler, Anna The Journal of Physical Chemistry B, Vol. 114, Issue 51 https://doi.org/10.1021/jp107357y	journal	December 2010
Ab initio Study of the Structural, Tautomeric, Pairing, and Electronic Properties of Seleno-Derivatives of Thymine Vázquez-Mayagoitia, Álvaro; Huertas, Oscar; Brancolini, Giorgia The Journal of Physical Chemistry B, Vol. 113, Issue 43 https://doi.org/10.1021/jp9057077	journal	October 2009
Synthesis, Characterization, and Structure−Property Relationship of Novel Fluorene−Thiophene-Based Conjugated Copolymers Liu, Bin; Yu, Wang-Lin; Lai, Yee-Hing Macromolecules, Vol. 33, Issue 24 https://doi.org/10.1021/ma000866p	journal	November 2000
Molecular Packing in Crystalline Poly(9,9-di- n -octyl-2,7-fluorene) Chen, S. H.; Chou, H. L.; Su, A. C. Macromolecules, Vol. 37, Issue 18 https://doi.org/10.1021/ma049346a	journal	August 2004
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
Triphenylamine−Fluorene Alternating Conjugated Copolymers with Pendant Acceptor Groups: Synthesis, Structure−Property Relationship, and Photovoltaic Application Zhang, Zhi-Guo; Zhang, Ke-Li; Liu, Gang Macromolecules, Vol. 42, Issue 8 https://doi.org/10.1021/ma900236h	journal	April 2009
Polyfluorene Derivatives: Effective Conjugation Lengths from Well-Defined Oligomers Klaerner, G.; Miller, R. D. Macromolecules, Vol. 31, Issue 6 https://doi.org/10.1021/ma971073e	journal	March 1998
Effect of o -Carborane on the Optoelectronic and Device-Level Properties of Poly(fluorene)s Davis, Andrew R.; Peterson, Joseph J.; Carter, Kenneth R. ACS Macro Letters, Vol. 1, Issue 4 https://doi.org/10.1021/mz300037u	journal	March 2012
Direct C−H Arylation of Purines: Development of Methodology and Its Use in Regioselective Synthesis of 2,6,8-Trisubstituted Purines Čerňa, Igor; Pohl, Radek; Klepetářová, Blanka Organic Letters, Vol. 8, Issue 23 https://doi.org/10.1021/ol062324j	journal	October 2006
DNA in a material world Seeman, Nadrian C. Nature, Vol. 421, Issue 6921 https://doi.org/10.1038/nature01406	journal	January 2003
Self-replication of information-bearing nanoscale patterns Wang, Tong; Sha, Ruojie; Dreyfus, Rémi Nature, Vol. 478, Issue 7368 https://doi.org/10.1038/nature10500	journal	October 2011
DNA assembly for nanopore data storage readout Lopez, Randolph; Chen, Yuan-Jyue; Dumas Ang, Siena Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-10978-4	journal	July 2019
Highly fluorescent donor–acceptor purines Butler, Roslyn S.; Myers, Andrea K.; Bellarmine, Prabhu J. Mater. Chem., Vol. 17, Issue 19 https://doi.org/10.1039/B618171F	journal	January 2007
Fluorescent thiophene-based materials and their outlook for emissive applications Rasmussen, Seth C.; Evenson, Sean J.; McCausland, Casey B. Chemical Communications, Vol. 51, Issue 22 https://doi.org/10.1039/C4CC09206F	journal	January 2015
Thieno[3,4- b ]pyrazine-based oligothiophenes: simple models of donor–acceptor polymeric materials Wen, Li; Heth, Christopher L.; Rasmussen, Seth C. Phys. Chem. Chem. Phys., Vol. 16, Issue 16 https://doi.org/10.1039/C4CP00312H	journal	January 2014
Exploiting nucleobase-containing materials – from monomers to complex morphologies using RAFT dispersion polymerization Kang, Yan; Pitto-Barry, Anaïs; Willcock, Helen Polymer Chemistry, Vol. 6, Issue 1 https://doi.org/10.1039/C4PY01074D	journal	January 2015
Solution-processed small molecules based on benzodithiophene and difluorobenzothiadiazole for inverted organic solar cells Liao, Xunfan; Wu, Feiyan; Zhang, Lifu Polymer Chemistry, Vol. 6, Issue 44 https://doi.org/10.1039/C5PY01051A	journal	January 2015
Optical properties and solvatofluorochromism of fluorene derivatives bearing S,S-dioxidized thiophene Nakahama, Tatsumoto; Kitagawa, Daichi; Sotome, Hikaru Photochemical & Photobiological Sciences, Vol. 15, Issue 10 https://doi.org/10.1039/C6PP00126B	journal	January 2016
Influence of structure–property relationships of two structural isomers of thiophene-flanked diazaisoindigo on carrier-transport properties Ashizawa, Minoru; Hasegawa, Tsukasa; Kawauchi, Susumu RSC Advances, Vol. 6, Issue 111 https://doi.org/10.1039/C6RA17424H	journal	January 2016
Eco-friendly direct (hetero)-arylation polymerization: scope and limitation Yu, Simiao; Liu, Fuchuan; Yu, Jianwei Journal of Materials Chemistry C, Vol. 5, Issue 1 https://doi.org/10.1039/C6TC04240F	journal	January 2017
Direct C–H arylation: a “Greener” approach towards facile synthesis of organic semiconducting molecules and polymers Bohra, Hassan; Wang, Mingfeng Journal of Materials Chemistry A, Vol. 5, Issue 23 https://doi.org/10.1039/C7TA00617A	journal	January 2017
Efficient white-light emission from a single polymer system with “spring-like” self-assemblies induced emission enhancement and intramolecular charge transfer characteristics Ravindran, Ezhakudiyan; Somanathan, Narayanasastri Journal of Materials Chemistry C, Vol. 5, Issue 19 https://doi.org/10.1039/C7TC01036B	journal	January 2017
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
Regioselective C–H and N–H functionalization of purine derivatives and analogues: a synthetic and mechanistic perspective Mondal, Manoj; Begum, Tahshina; Bharali, Pankaj Catalysis Science & Technology, Vol. 8, Issue 23 https://doi.org/10.1039/C8CY01860J	journal	January 2018
Synthesis of a soluble adenine-functionalized polythiophene through direct arylation polymerization and its fluorescence responsive behavior Sabury, Sina; Collier, Graham S.; Ericson, M. Nance Polymer Chemistry, Vol. 11, Issue 4 https://doi.org/10.1039/C9PY01142K	journal	January 2020
All-organic fast intersystem crossing assisted exciplexes exhibiting sub-microsecond thermally activated delayed fluorescence Traskovskis, Kaspars; Sebris, Armands; Novosjolova, Irina Journal of Materials Chemistry C, Vol. 9, Issue 13 https://doi.org/10.1039/D0TC05099G	journal	January 2021
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
DNA-programmed assembly of nanostructures Gothelf, Kurt V.; LaBean, Thomas H. Organic & Biomolecular Chemistry, Vol. 3, Issue 22 https://doi.org/10.1039/b510551j	journal	January 2005
Self-complementary purines by quadruple hydrogen bonding Martin, Alisha M.; Butler, Roslyn S.; Ghiviriga, Ion Chemical Communications, Issue 42 https://doi.org/10.1039/b610239e	journal	January 2006
Ultraviolet-violet electroluminescence from highly fluorescent purines Yang, Yixing; Cohn, Pamela; Eom, Sang-Hyun Journal of Materials Chemistry C, Vol. 1, Issue 16 https://doi.org/10.1039/c3tc00734k	journal	January 2013
A new local density functional for main-group thermochemistry, transition metal bonding, thermochemical kinetics, and noncovalent interactions Zhao, Yan; Truhlar, Donald G. The Journal of Chemical Physics, Vol. 125, Issue 19, Article No. 194101 https://doi.org/10.1063/1.2370993	journal	November 2006
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Direct observation of the intersystem crossing in poly(3‐octylthiophene) Kraabel, B.; Moses, D.; Heeger, A. J. The Journal of Chemical Physics, Vol. 103, Issue 12 https://doi.org/10.1063/1.470597	journal	September 1995
DFTB+, a software package for efficient approximate density functional theory based atomistic simulations Hourahine, B.; Aradi, B.; Blum, V. The Journal of Chemical Physics, Vol. 152, Issue 12 https://doi.org/10.1063/1.5143190	journal	March 2020
Unraveling the Inhomogeneously Broadened Absorption Spectrum of Conjugated Polymers by Single-Molecule Light-Harvesting Action Spectroscopy Walter, Manfred J.; Lupton, John M. Physical Review Letters, Vol. 103, Issue 16 https://doi.org/10.1103/PhysRevLett.103.167401	journal	October 2009
Principles and Applications of Solvatochromism Nigam, Shalini; Rutan, Sarah Applied Spectroscopy, Vol. 55, Issue 11 https://doi.org/10.1366/0003702011953702	journal	November 2001
Photophysical properties and quantum chemical studies of poly(2,7-9,9'-dihexylfluorene-dyil) Oliveira, Hueder P. M.; Martins, Tatiana D.; Honório, Kathia M. Journal of the Brazilian Chemical Society, Vol. 20, Issue 1 https://doi.org/10.1590/S0103-50532009000100024	journal	January 2009

Similar Records

Linking design and properties of purine-based donor–acceptor chromophores as optoelectronic materials

Journal Article · Mon Jul 03 00:00:00 EDT 2017 · Journal of Materials Chemistry C · OSTI ID:1649656

Random Copolymers Allow Control of Crystallization and Microphase Separation in Fully Conjugated Block Copolymers

Journal Article · Sun Oct 28 20:00:00 EDT 2018 · Macromolecules · OSTI ID:1656476

A single polymeric template-based full color organic electrochromic device

Journal Article · Thu Jan 31 19:00:00 EST 2019 · ACS Applied Materials and Interfaces · OSTI ID:1498761

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
conjugated polymer
cross-conjugated
density functional theory
direct arylation polymerization
electronic structure
highly fluorescent
purine

Highly fluorescent purine-containing conjugated copolymers with tailored optoelectronic properties

Citation Formats

References (80)

Similar Records

Related Subjects