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

Collier, Graham S.; Brown, Lauren A.; Boone, Evan S.; Kaushal, Meesha; Ericson, Milton Nance; Walter, Michael G.; Long, Brian K.; Kilbey, S. Michael

doi:10.1039/c7tc01835e

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

DOI:https://doi.org/10.1039/c7tc01835e· OSTI ID:1649656

Collier, Graham S. ^[1]; Brown, Lauren A. ^[1]; Boone, Evan S. ^[2]; Kaushal, Meesha ^[3]; ^[4]; ^[3]; ^[1]; ^[5]

Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemistry
Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemical and Biomolecular Engineering
Univ. of North Carolina, Charlotte, NC (United States). Dept. of Chemistry
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Electrical and Electronics Systems Research Division
Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemistry and Dept. of Chemical and Biomolecular Engineering

Creating new building blocks for donor–acceptor conjugated systems is an important task for continued development of materials for organic electronics. Here, purines were introduced into small-molecule π-conjugated systems via Stille cross-coupling using stannylated derivatives of benzodithiophene, thiophene, or dithienylbenzothiadiazole to generate a series of “purine–π–purine” chromophores having high thermal stability, long excited-state lifetimes, and high quantum yields. Photophysical and electrochemical property characterization indicate that depending on the choice of a conjugated bridging unit, purines behave as either an electron-donating or an electron-accepting unit in these small-molecule donor–acceptor chromophores. Specifically, while purine chromophores do not exhibit charge transfer character when linked to a thiophene unit, purinyl units act as a weak acceptor when coupled with benzodithiophene and as a weak donor when coupled with dithienylbenzothiadiazole. In addition to fundamental insights into the molecular design of purine-based chromophores and their charge-transfer character, the results and synthetic tailorability of purines suggest that they may be compelling building blocks in conjugated materials for optical and electronic devices and sensors.

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

Sponsoring Organization:: USDOE Laboratory Directed Research and Development (LDRD) Program; US Army Research Office (ARO)

DOE Contract Number:: AC05-00OR22725

OSTI ID:: 1649656

Journal Information:: Journal of Materials Chemistry C, Journal Name: Journal of Materials Chemistry C Journal Issue: 27 Vol. 5; ISSN 2050-7526

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

References (34)

Principles of Fluorescence Spectroscopy Lakowicz, Joseph R. Springer New York, NY https://doi.org/10.1007/978-0-387-46312-4	book	January 2006
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
Conjugated Polymer-Based Chemical Sensors McQuade, D. Tyler; Pullen, Anthony E.; Swager, Timothy M. Chemical Reviews, Vol. 100, Issue 7 https://doi.org/10.1021/cr9801014	journal	July 2000
The Suzuki-Miyaura Cross-Coupling Reactions of 6-Halopurines with Boronic Acids Leading to 6-Aryl- and 6-Alkenylpurines Havelková, Martina; Hocek, Michal; Česnek, Michal Synlett, Vol. 1999, Issue 7 https://doi.org/10.1055/s-1999-2753	journal	July 1999
Push-Pull-Type Purine Nucleoside-Based Fluorescent Sensors for the Selective Detection of Pd ²⁺ in Aqueous Buffer: Push-Pull-Type Purine Nucleoside-Based Fluorescent Sensors Li, Jian-Ping; Wang, Hui-Xuan; Wang, Hai-Xia European Journal of Organic Chemistry, Vol. 2014, Issue 11 https://doi.org/10.1002/ejoc.201301897	journal	March 2014
The Influence of Solubilizing Chain Stereochemistry on Small Molecule Photovoltaics Zerdan, Raghida Bou; Shewmon, Nathan T.; Zhu, Yu Advanced Functional Materials, Vol. 24, Issue 38 https://doi.org/10.1002/adfm.201401030	journal	July 2014
Novel red-emitting fluorene-based copolymers Hou, Qiong; Xu, Yishe; Yang, Wei Journal of Materials Chemistry, Vol. 12, Issue 10 https://doi.org/10.1039/b203862e	journal	August 2002
Benzothiadiazole and its π-extended, heteroannulated derivatives: useful acceptor building blocks for high-performance donor–acceptor polymers in organic electronics Wang, Yang; Michinobu, Tsuyoshi Journal of Materials Chemistry C, Vol. 4, Issue 26 https://doi.org/10.1039/C6TC01860B	journal	January 2016
Stille Polycondensation for Synthesis of Functional Materials Carsten, Bridget; He, Feng; Son, Hae Jung Chemical Reviews, Vol. 111, Issue 3 https://doi.org/10.1021/cr100320w	journal	March 2011
It Takes More Than an Imine: The Role of the Central Atom on the Electron-Accepting Ability of Benzotriazole and Benzothiadiazole Oligomers Patel, Dinesh G. (Dan); Feng, Fude; Ohnishi, Yu-ya Journal of the American Chemical Society, Vol. 134, Issue 5 https://doi.org/10.1021/ja207978v	journal	January 2012
Organic light emitting diodes: Energy saving lighting technology—A review Thejo Kalyani, N.; Dhoble, S. J. Renewable and Sustainable Energy Reviews, Vol. 16, Issue 5 https://doi.org/10.1016/j.rser.2012.02.021	journal	June 2012
The Suzuki-Miyaura Cross-Coupling Reactionsof 2-, 6- or 8-Halopurines with Boronic Acids Leading to 2-, 6- or 8-Aryl- and -Alkenylpurine Derivatives Havelková, Martina; Dvořak, Dalimil; Hocek, Michal Synthesis, Vol. 2001, Issue 11 https://doi.org/10.1055/s-2001-16765	journal	January 2001
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
π-Extended Thiadiazoles Fused with Thienopyrrole or Indole Moieties: Synthesis, Structures, and Properties Kato, Shin-ichiro; Furuya, Takayuki; Kobayashi, Atsushi The Journal of Organic Chemistry, Vol. 77, Issue 17 https://doi.org/10.1021/jo301458m	journal	August 2012
Intramolecular Charge Transfer Assisted by Conformational Changes in the Excited State of Fluorene-dibenzothiophene- S,S -dioxide Co-oligomers Dias, Fernando B.; Pollock, Sam; Hedley, Gordon The Journal of Physical Chemistry B, Vol. 110, Issue 39 https://doi.org/10.1021/jp0643653	journal	October 2006
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
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
Rational Design of High Performance Conjugated Polymers for Organic Solar Cells Zhou, Huaxing; Yang, Liqiang; You, Wei Macromolecules, Vol. 45, Issue 2 https://doi.org/10.1021/ma201648t	journal	January 2012
Recent Advances in Bulk Heterojunction Polymer Solar Cells Lu, Luyao; Zheng, Tianyue; Wu, Qinghe Chemical Reviews, Vol. 115, Issue 23 https://doi.org/10.1021/acs.chemrev.5b00098	journal	August 2015
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
Color Control in π-Conjugated Organic Polymers for Use in Electrochromic Devices Beaujuge, Pierre M.; Reynolds, John R. Chemical Reviews, Vol. 110, Issue 1, p. 268-320 https://doi.org/10.1021/cr900129a	journal	January 2010
Electronic properties, hydrogen bonding, stacking, and cation binding of DNA and RNA bases ?poner, Ji?�; Leszczynski, Jerzy; Hobza, Pavel Biopolymers, Vol. 61, Issue 1 https://doi.org/10.1002/1097-0282(2001)61:1<3::AID-BIP10048>3.0.CO;2-4	journal	January 2001
Synthesis, Photophysical Behavior, and Electronic Structure of Push−Pull Purines Butler, Roslyn S.; Cohn, Pamela; Tenzel, Phillip Journal of the American Chemical Society, Vol. 131, Issue 2 https://doi.org/10.1021/ja806348z	journal	January 2009
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
Effects of Stereoisomerism on the Crystallization Behavior and Optoelectrical Properties of Conjugated Molecules Liu, Jianhua; Zhang, Yuan; Phan, Hung Advanced Materials, Vol. 25, Issue 27 https://doi.org/10.1002/adma.201300255	journal	April 2013
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
Synthesis and Photovoltaic Properties of Copolymers from Benzodithiophene and Thiazole Yang, Miao; Peng, Bo; Liu, Bo The Journal of Physical Chemistry C, Vol. 114, Issue 41 https://doi.org/10.1021/jp1063885	journal	September 2010
Molecular rearrangement at charged states: Intrinsic effects upon photo and electroluminescence Wang, Zhixiang; Liu, Qingqing; Chen, Ting Dyes and Pigments, Vol. 113 https://doi.org/10.1016/j.dyepig.2014.09.017	journal	February 2015
25th Anniversary Article: Organic Field-Effect Transistors: The Path Beyond Amorphous Silicon Sirringhaus, Henning Advanced Materials, Vol. 26, Issue 9 https://doi.org/10.1002/adma.201304346	journal	January 2014
Synthesis and characterization of novel semiconducting polymers containing pyrimidine Gunathilake, Samodha S.; Magurudeniya, Harsha D.; Huang, Peishen Polymer Chemistry, Vol. 4, Issue 20 https://doi.org/10.1039/c3py00137g	journal	January 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
Small molecule semiconductors for high-efficiency organic photovoltaics Lin, Yuze; Li, Yongfang; Zhan, Xiaowei Chemical Society Reviews, Vol. 41, Issue 11 https://doi.org/10.1039/c2cs15313k	journal	January 2012
Efficient intersystem crossing using singly halogenated carbomethoxyphenyl porphyrins measured using delayed fluorescence, chemical quenching, and singlet oxygen emission Marin, Dawn M.; Payerpaj, Sonia; Collier, Graham S. Physical Chemistry Chemical Physics, Vol. 17, Issue 43 https://doi.org/10.1039/C5CP04359J	journal	January 2015
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

Similar Records

Highly fluorescent purine-containing conjugated copolymers with tailored optoelectronic properties

Journal Article · Fri Aug 12 00:00:00 EDT 2022 · Polymer Chemistry · OSTI ID:1883818

Topology and ground state control in open-shell donor-acceptor conjugated polymers

Journal Article · Wed Jun 16 00:00:00 EDT 2021 · Cell Reports Physical Science · OSTI ID:1985337

Optoelectronic properties and charge transfer in donor-acceptor all-conjugated diblock copolymers.

Journal Article · Thu May 12 00:00:00 EDT 2011 · J. Phys. Chem. C · OSTI ID:1015945

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

Citation Formats

References (34)

Similar Records

Related Subjects