From computational discovery to experimental characterization of a high hole mobility organic crystal

Sokolov, Anatoliy N.; Atahan-Evrenk, Sule; Mondal, Rajib; Akkerman, Hylke B.; Sánchez-Carrera, Roel S.; Granados-Focil, Sergio; Schrier, Joshua; Mannsfeld, Stefan C. B.; Zoombelt, Arjan P.; Bao, Zhenan; Aspuru-Guzik, Alán

doi:10.1038/ncomms1451

From computational discovery to experimental characterization of a high hole mobility organic crystal

Journal Article · Tue Aug 16 04:00:00 EDT 2011 · Nature Communications

DOI:https://doi.org/10.1038/ncomms1451· OSTI ID:1623876

Sokolov, Anatoliy N. ^[1]; Atahan-Evrenk, Sule ^[2]; Mondal, Rajib ^[3]; Akkerman, Hylke B. ^[3]; Sánchez-Carrera, Roel S. ^[2]; Granados-Focil, Sergio ^[4]; Schrier, Joshua ^[5]; Mannsfeld, Stefan C. B. ^[6]; Zoombelt, Arjan P. ^[3]; Bao, Zhenan ^[3]; Aspuru-Guzik, Alán ^[2]

Stanford Univ., CA (United States). Dept. of Chemical Engineering; DOE/OSTI
Harvard Univ., Cambridge, MA (United States). Dept. of Chemistry and Chemical Biology
Stanford Univ., CA (United States). Dept. of Chemical Engineering
Clark Univ., Worcester, MA (United States). Dept. of Chemistry
Haverford College, Haverford, PA (United States). Dept. of Chemistry
SLAC National Accelerator Lab., Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource (SSRL)

For organic semiconductors to find ubiquitous electronics applications, the development of new materials with high mobility and air stability is critical. Despite the versatility of carbon, exploratory chemical synthesis in the vast chemical space can be hindered by synthetic and characterization difficulties. Here we show that in silico screening of novel derivatives of the dinaphtho[2,3-b:2',3'-f]thieno[3,2-b]thiophene semiconductor with high hole mobility and air stability can lead to the discovery of a new high-performance semiconductor. On the basis of estimates from the Marcus theory of charge transfer rates, we identified a novel compound expected to demonstrate a theoretic twofold improvement in mobility over the parent molecule. Synthetic and electrical characterization of the compound is reported with single-crystal fieldeffect transistors, showing a remarkable saturation and linear mobility of 12.3 and 16cm2V-1 s-1 , respectively. This is one of the very few organic semiconductors with mobility greater than 10cm2V-1 s-1 reported to date.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1623876

Journal Information:: Nature Communications, Journal Name: Nature Communications Journal Issue: 1 Vol. 2; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

References (65)

Chemical and Physical Sensing by Organic Field-Effect Transistors and Related Devices Someya, Takao; Dodabalapur, Ananth; Huang, Jia Advanced Materials, Vol. 22, Issue 34 https://doi.org/10.1002/adma.200902760	journal	July 2010
Alkylated Dinaphtho[2,3-b:2′,3′-f]Thieno[3,2-b]Thiophenes (Cn-DNTTs): Organic Semiconductors for High-Performance Thin-Film Transistors Kang, Myeong Jin; Doi, Iori; Mori, Hiroki Advanced Materials, Vol. 23, Issue 10 https://doi.org/10.1002/adma.201001283	journal	August 2010
Predicting organic thin-film transistor carrier type from single molecule calculations Subhas, Adam V.; Whealdon, Jennifer; Schrier, Joshua Computational and Theoretical Chemistry, Vol. 966, Issue 1-3 https://doi.org/10.1016/j.comptc.2011.02.015	journal	June 2011
Organic Thin-Film Transistors as Plastic Analytical Sensors Torsi, Luisa; Dodabalapur, Ananth Analytical Chemistry, Vol. 77, Issue 19 https://doi.org/10.1021/ac053475n	journal	October 2005
Computed Crystal Energy Landscapes for Understanding and Predicting Organic Crystal Structures and Polymorphism Price, Sarah (Sally) L. Accounts of Chemical Research, Vol. 42, Issue 1 https://doi.org/10.1021/ar800147t	journal	January 2009
Charge-Transfer and Energy-Transfer Processes in π-Conjugated Oligomers and Polymers: A Molecular Picture Brédas, Jean-Luc; Beljonne, David; Coropceanu, Veaceslav Chemical Reviews, Vol. 104, Issue 11 https://doi.org/10.1021/cr040084k	journal	November 2004
Pentacene Disproportionation during Sublimation for Field-Effect Transistors Roberson, Luke B.; Kowalik, Janusz; Tolbert, Laren M. Journal of the American Chemical Society, Vol. 127, Issue 9 https://doi.org/10.1021/ja044586r	journal	March 2005
Nitrogen-Rich Oligoacenes: Candidates for n-Channel Organic Semiconductors Winkler, Michael; Houk, K. N. Journal of the American Chemical Society, Vol. 129, Issue 6 https://doi.org/10.1021/ja067087u	journal	February 2007
Facile Synthesis of Highly π-Extended Heteroarenes, Dinaphtho[2,3- b :2‘,3‘- f ]chalcogenopheno[3,2- b ]chalcogenophenes, and Their Application to Field-Effect Transistors Yamamoto, Tatsuya; Takimiya, Kazuo Journal of the American Chemical Society, Vol. 129, Issue 8 https://doi.org/10.1021/ja068429z	journal	February 2007
Toward a Rational Design of Poly(2,7-Carbazole) Derivatives for Solar Cells Blouin, Nicolas; Michaud, Alexandre; Gendron, David Journal of the American Chemical Society, Vol. 130, Issue 2, p. 732-742 https://doi.org/10.1021/ja0771989	journal	January 2008
Dianthra[2,3- b :2′,3′- f ]thieno[3,2- b ]thiophene (DATT): Synthesis, Characterization, and FET Characteristics of New π-Extended Heteroarene with Eight Fused Aromatic Rings Niimi, Kazuki; Shinamura, Shoji; Osaka, Itaru Journal of the American Chemical Society, Vol. 133, Issue 22 https://doi.org/10.1021/ja202377m	journal	June 2011
Towards high charge-carrier mobilities by rational design of the shape and periphery of discotics Feng, Xinliang; Marcon, Valentina; Pisula, Wojciech Nature Materials, Vol. 8, Issue 5 https://doi.org/10.1038/nmat2427	journal	April 2009
Advances in methods and algorithms in a modern quantum chemistry program package Shao, Yihan; Molnar, Laszlo Fusti; Jung, Yousung Phys. Chem. Chem. Phys., Vol. 8, Issue 27 https://doi.org/10.1039/b517914a	journal	January 2006
Energetics and stability of pentacene thin films on amorphous and crystalline octadecylsilane modified surfaces Virkar, Ajay A.; Mannsfeld, Stefan C. B.; Bao, Zhenan Journal of Materials Chemistry, Vol. 20, Issue 13 https://doi.org/10.1039/b921767c	journal	January 2010
Ultrafast carrier dynamics in pentacene, functionalized pentacene, tetracene, and rubrene single crystals Ostroverkhova, O.; Cooke, D. G.; Hegmann, F. A. Applied Physics Letters, Vol. 88, Issue 16 https://doi.org/10.1063/1.2193801	journal	April 2006
An Improved Synthesis of 2-Anthraldehyde Arjunan, Palanisamy; Berlin, K. Darrell Organic Preparations and Procedures International, Vol. 13, Issue 5 https://doi.org/10.1080/00304948109356143	journal	October 1981
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/physrevlett.77.3865	journal	October 1996
A test of crystal structure prediction of small organic molecules Lommerse, Jos P. M.; Motherwell, W. D. Sam; Ammon, Herman L. Acta Crystallographica Section B Structural Science, Vol. 56, Issue 4 https://doi.org/10.1107/s0108768100004584	journal	August 2000
Significant progress in predicting the crystal structures of small organic molecules – a report on the fourth blind test Day, Graeme M.; Cooper, Timothy G.; Cruz-Cabeza, Aurora J. Acta Crystallographica Section B Structural Science, Vol. 65, Issue 2 https://doi.org/10.1107/s0108768109004066	journal	March 2009
Elastomeric Transistor Stamps: Reversible Probing of Charge Transport in Organic Crystals Sundar, Vikram C.; Zaumseil, Jana; Podzorov, Vitaly Science, Vol. 303, Issue 5664, p. 1644-1646 https://doi.org/10.1126/science.1094196	journal	March 2004
Development of New Semiconducting Materials for Durable High-performance Air-stable Organic Field-effect Transistors Takimiya, Kazuo; Kunugi, Yoshihito; Otsubo, Tetsuo Chemistry Letters, Vol. 36, Issue 5 https://doi.org/10.1246/cl.2007.578	journal	May 2007
The effect of impurities on the mobility of single crystal pentacene Jurchescu, Oana D.; Baas, Jacob; Palstra, Thomas T. M. arXiv https://doi.org/10.48550/arxiv.cond-mat/0404130	text	January 2004
High-Performance n- and p-Type Single-Crystal Organic Transistors with Free-Space Gate Dielectrics Menard, E.; Podzorov, V.; Hur, S.-H. Advanced Materials, Vol. 16, Issue 23-24, p. 2097-2101 https://doi.org/10.1002/adma.200401017	journal	December 2004
High-Resolution Measurement of the Anisotropy of Charge Transport in Single Crystals Reese, C.; Bao, Z. Advanced Materials, Vol. 19, Issue 24 https://doi.org/10.1002/adma.200701139	journal	December 2007
Polymer–Fullerene Composite Solar Cells Thompson, Barry C.; Fréchet, Jean M. J. Angewandte Chemie International Edition, Vol. 47, Issue 1, p. 58-77 https://doi.org/10.1002/anie.200702506	journal	January 2008
Charge-Transfer and Energy-Transfer Processes in ?-Conjugated Oligomers and Polymers: A Molecular Picture Bredas, Jean-Luc; Beljonne, David; Coropceanu, Veaceslav ChemInform, Vol. 36, Issue 5 https://doi.org/10.1002/chin.200505257	journal	February 2005
Charge Transport in Organic Semiconductors Coropceanu, Veaceslav; Cornil, Jerome; da Silva Filho, Demetrio A. ChemInform, Vol. 38, Issue 29 https://doi.org/10.1002/chin.200729266	journal	July 2007
Development of New Semiconducting Materials for Durable High-Performance Air-Stable Organic Field-Effect Transistors. Takimiya, Kazuo; Kunugi, Yoshihito; Otsubo, Tetsuo ChemInform, Vol. 38, Issue 38 https://doi.org/10.1002/chin.200738220	journal	September 2007
Physical vapor growth of centimeter-sized crystals of α-hexathiophene Kloc, Ch.; Simpkins, P. G.; Siegrist, T. Journal of Crystal Growth, Vol. 182, Issue 3-4 https://doi.org/10.1016/S0022-0248(97)00370-9	journal	December 1997
Organic single-crystal field-effect transistors Reese, Colin; Bao, Zhenan Materials Today, Vol. 10, Issue 3, p. 20-27 https://doi.org/10.1016/S1369-7021(07)70016-0	journal	March 2007
Fabrication of low-cost electronic biosensors Sokolov, Anatoliy N.; Roberts, Mark E.; Bao, Zhenan Materials Today, Vol. 12, Issue 9 https://doi.org/10.1016/S1369-7021(09)70247-0	journal	September 2009
USPEX—Evolutionary crystal structure prediction Glass, Colin W.; Oganov, Artem R.; Hansen, Nikolaus Computer Physics Communications, Vol. 175, Issue 11-12 https://doi.org/10.1016/j.cpc.2006.07.020	journal	December 2006
XtalOpt: An open-source evolutionary algorithm for crystal structure prediction Lonie, David C.; Zurek, Eva Computer Physics Communications, Vol. 182, Issue 2 https://doi.org/10.1016/j.cpc.2010.07.048	journal	February 2011
Design strategy for air-stable organic semiconductors applicable to high-performance field-effect transistors Takimiya, Kazuo; Yamamoto, Tatsuya; Ebata, Hideaki Science and Technology of Advanced Materials, Vol. 8, Issue 4 https://doi.org/10.1016/j.stam.2007.02.010	journal	January 2007
Cross-Linked Polymer Gate Dielectric Films for Low-Voltage Organic Transistors Roberts, Mark E.; Queraltó, Núria; Mannsfeld, Stefan C. B. Chemistry of Materials, Vol. 21, Issue 11 https://doi.org/10.1021/cm900637p	journal	June 2009
Charge Transport in Organic Semiconductors Coropceanu, Veaceslav; Cornil, Jérôme; da Silva Filho, Demetrio A. Chemical Reviews, Vol. 107, Issue 4 https://doi.org/10.1021/cr050140x	journal	April 2007
DREIDING: a generic force field for molecular simulations Mayo, Stephen L.; Olafson, Barry D.; Goddard, William A. The Journal of Physical Chemistry, Vol. 94, Issue 26, p. 8897-8909 https://doi.org/10.1021/j100389a010	journal	December 1990
Polarization Energies in Oligoacene Semiconductor Crystals Norton, Joseph E.; Brédas, Jean-Luc Journal of the American Chemical Society, Vol. 130, Issue 37 https://doi.org/10.1021/ja8017797	journal	September 2008
Predictions of Hole Mobilities in Oligoacene Organic Semiconductors from Quantum Mechanical Calculations ^† Deng, Wei-Qiao; Goddard, William A. The Journal of Physical Chemistry B, Vol. 108, Issue 25 https://doi.org/10.1021/jp0495848	journal	June 2004
Comparison of DFT Methods for Molecular Orbital Eigenvalue Calculations Zhang, Gang; Musgrave, Charles B. The Journal of Physical Chemistry A, Vol. 111, Issue 8 https://doi.org/10.1021/jp061633o	journal	March 2007
Theoretical Characterization of the Air-Stable, High-Mobility Dinaphtho[2,3- b :2′3′- f ]thieno[3,2- b ]-thiophene Organic Semiconductor Sánchez-Carrera, Roel S.; Atahan, Sule; Schrier, Joshua The Journal of Physical Chemistry C, Vol. 114, Issue 5 https://doi.org/10.1021/jp910102f	journal	January 2010
Evaluation of the External Reorganization Energy of Polyacenes McMahon, David P.; Troisi, Alessandro The Journal of Physical Chemistry Letters, Vol. 1, Issue 6 https://doi.org/10.1021/jz1001049	journal	February 2010
Failure of Conventional Density Functionals for the Prediction of Molecular Crystal Polymorphism: A Quantum Monte Carlo Study Hongo, Kenta; Watson, Mark A.; Sánchez-Carrera, Roel S. The Journal of Physical Chemistry Letters, Vol. 1, Issue 12 https://doi.org/10.1021/jz100418p	journal	May 2010
Predicting Organic Crystal Lattice Energies with Chemical Accuracy Beran, Gregory J. O.; Nanda, Kaushik The Journal of Physical Chemistry Letters, Vol. 1, Issue 24 https://doi.org/10.1021/jz101383z	journal	December 2010
Ion conformation and orientational order in a dicationic ionic liquid crystal studied by solid-state nuclear magnetic resonance spectroscopy Majhi, Debashis; Dvinskikh, Sergey V. Scientific Reports, Vol. 11, Issue 1 https://doi.org/10.1038/s41598-021-85021-y	journal	March 2021
Advances in methods and algorithms in a modern quantum chemistry program package Shao, Yihan; Molnar, Laszlo Fusti; Jung, Yousung Phys. Chem. Chem. Phys., Vol. 8, Issue 27 https://doi.org/10.1039/B517914A	journal	January 2006
Role of computer simulations in structure prediction and structure determination: from molecular compounds to hybrid frameworks Mellot-Draznieks, Caroline Journal of Materials Chemistry, Vol. 17, Issue 41 https://doi.org/10.1039/b702516p	journal	January 2007
Fused aromatic thienopyrazines: structure, properties and function Mondal, Rajib; Ko, Sangwon; Bao, Zhenan Journal of Materials Chemistry, Vol. 20, Issue 47 https://doi.org/10.1039/c0jm01840f	journal	January 2010
Electronic sensing of vapors with organic transistors Crone, B.; Dodabalapur, A.; Gelperin, A. Applied Physics Letters, Vol. 78, Issue 15 https://doi.org/10.1063/1.1360785	journal	April 2001
Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules Hehre, W. J.; Ditchfield, R.; Pople, J. A. The Journal of Chemical Physics, Vol. 56, Issue 5, p. 2257-2261 https://doi.org/10.1063/1.1677527	journal	March 1972
Effect of impurities on the mobility of single crystal pentacene Jurchescu, Oana D.; Baas, Jacob; Palstra, Thomas T. M. Applied Physics Letters, Vol. 84, Issue 16 https://doi.org/10.1063/1.1704874	journal	April 2004
High-performance microscale single-crystal transistors by lithography on an elastomer dielectric Reese, Colin; Chung, Wook-Jin; Ling, Mang-mang Applied Physics Letters, Vol. 89, Issue 20 https://doi.org/10.1063/1.2388151	journal	November 2006
Enhancement of tetracene photovoltaic devices with heat treatment Shao, Yan; Sista, Srinivas; Chu, Chih-Wei Applied Physics Letters, Vol. 90, Issue 10 https://doi.org/10.1063/1.2709505	journal	March 2007
High-performance dinaphtho-thieno-thiophene single crystal field-effect transistors Haas, Simon; Takahashi, Yukihiro; Takimiya, Kazuo Applied Physics Letters, Vol. 95, Issue 2 https://doi.org/10.1063/1.3183509	journal	July 2009
Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions Krishnan, R.; Binkley, J. S.; Seeger, R. The Journal of Chemical Physics, Vol. 72, Issue 1 https://doi.org/10.1063/1.438955	journal	January 1980
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
Water-stable organic transistors and their application in chemical and biological sensors Roberts, M. E.; Mannsfeld, S. C. B.; Queralto, N. Proceedings of the National Academy of Sciences, Vol. 105, Issue 34 https://doi.org/10.1073/pnas.0802105105	journal	August 2008
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Free-electron-like Hall effect in high-mobility organic thin-film transistors Yamagishi, M.; Soeda, J.; Uemura, T. Physical Review B, Vol. 81, Issue 16 https://doi.org/10.1103/PhysRevB.81.161306	journal	April 2010
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
A test of crystal structure prediction of small organic molecules Lommerse, Jos P. M.; Motherwell, W. D. Sam; Ammon, Herman L. Acta Crystallographica Section B Structural Science, Vol. 56, Issue 4 https://doi.org/10.1107/S0108768100004584	journal	August 2000
Significant progress in predicting the crystal structures of small organic molecules – a report on the fourth blind test Day, Graeme M.; Cooper, Timothy G.; Cruz-Cabeza, Aurora J. Acta Crystallographica Section B Structural Science, Vol. 65, Issue 2 https://doi.org/10.1107/S0108768109004066	journal	March 2009
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Robert, Parr,; Chengteh, Lee,; Weitao, Yang, The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/zrp0-ry04	text	January 1988
Organic field-effect transistors Małachowski, M.; Żmija, J. Opto-Electronics Review, Vol. 18, Issue 2 https://doi.org/10.2478/s11772-010-0008-9	journal	January 2010
FET Characteristics of Dinaphthothienothiophene (DNTT) on Si/SiO2 Substrates with Various Surface-Modifications Yamamoto, Tatsuya; Takimiya, Kazuo Journal of Photopolymer Science and Technology, Vol. 20, Issue 1 https://doi.org/10.2494/photopolymer.20.57	journal	January 2007

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Ultra-high mobility transparent organic thin film transistors grown by an off-centre spin-coating method Yuan, Yongbo; Giri, Gaurav; Ayzner, Alexander L. Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms4005	journal	January 2014
High operational and environmental stability of high-mobility conjugated polymer field-effect transistors through the use of molecular additives Nikolka, Mark; Nasrallah, Iyad; Rose, Bradley Nature Materials, Vol. 16, Issue 3 https://doi.org/10.1038/nmat4785	journal	December 2016
Charge-transfer dynamics and nonlocal dielectric permittivity tuned with metamaterial structures as solvent analogues Lee, Kwang Jin; Xiao, Yiming; Woo, Jae Heun Nature Materials, Vol. 16, Issue 7 https://doi.org/10.1038/nmat4907	journal	June 2017
Photonic quantum simulators Aspuru-Guzik, Alán; Walther, Philip Nature Physics, Vol. 8, Issue 4 https://doi.org/10.1038/nphys2253	journal	April 2012
Inverse design in search of materials with target functionalities Zunger, Alex Nature Reviews Chemistry, Vol. 2, Issue 4 https://doi.org/10.1038/s41570-018-0121	journal	March 2018
Accelerating the discovery of materials for clean energy in the era of smart automation Tabor, Daniel P.; Roch, Loïc M.; Saikin, Semion K. Nature Reviews Materials, Vol. 3, Issue 5 https://doi.org/10.1038/s41578-018-0005-z	journal	April 2018
Structure prediction drives materials discovery Oganov, Artem R.; Pickard, Chris J.; Zhu, Qiang Nature Reviews Materials, Vol. 4, Issue 5 https://doi.org/10.1038/s41578-019-0101-8	journal	April 2019
Easily doped p-type, low hole effective mass, transparent oxides Sarmadian, Nasrin; Saniz, Rolando; Partoens, Bart Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep20446	journal	February 2016
Accelerated computational discovery of high-performance materials for organic photovoltaics by means of cheminformatics Olivares-Amaya, Roberto; Amador-Bedolla, Carlos; Hachmann, Johannes Energy & Environmental Science, Vol. 4, Issue 12 https://doi.org/10.1039/c1ee02056k	journal	January 2011
An expedient synthesis of fused heteroacenes bearing a pyrrolo[3,2-b]pyrrole core Qiu, Li; Yu, Chunmeng; Zhao, Na Chemical Communications, Vol. 48, Issue 100 https://doi.org/10.1039/c2cc36689d	journal	January 2012
Predicting self-assembly: from empirism to determinism Palma, Carlos-Andres; Cecchini, Marco; Samorì, Paolo Chemical Society Reviews, Vol. 41, Issue 10 https://doi.org/10.1039/c2cs15302e	journal	January 2012
First principles high throughput screening of oxynitrides for water-splitting photocatalysts Wu, Yabi; Lazic, Predrag; Hautier, Geoffroy Energy Environ. Sci., Vol. 6, Issue 1 https://doi.org/10.1039/c2ee23482c	journal	January 2013
First-principles prediction of charge mobility in carbon and organic nanomaterials Xi, Jinyang; Long, Mengqiu; Tang, Ling Nanoscale, Vol. 4, Issue 15 https://doi.org/10.1039/c2nr30585b	journal	January 2012
Locking high energy 1D chain of dichloromethane molecules containing abnormally short Cl⋯Cl contacts of 2.524 Å inside organic crystals Zhou, Feng; Fu, Haoliang; Ong, Wei Qiang Organic & Biomolecular Chemistry, Vol. 10, Issue 29 https://doi.org/10.1039/c2ob25888a	journal	January 2012
High performance organic field-effect transistors based on single-crystal microribbons and microsheets of solution-processed dithieno[3,2-b:2′,3′-d]thiophene derivatives Yang, Yu Seok; Yasuda, Takuma; Kakizoe, Hayato Chemical Communications, Vol. 49, Issue 58 https://doi.org/10.1039/c3cc42114g	journal	January 2013
From charge transport parameters to charge mobility in organic semiconductors through multiscale simulation Shuai, Zhigang; Geng, Hua; Xu, Wei Chemical Society Reviews, Vol. 43, Issue 8 https://doi.org/10.1039/c3cs60319a	journal	January 2014
1,5-, 2,6- and 9,10-distyrylanthracenes as luminescent organic semiconductors Dadvand, Afshin; Sun, Wei-Hsin; Moiseev, Andrey G. Journal of Materials Chemistry C, Vol. 1, Issue 16 https://doi.org/10.1039/c3tc30247d	journal	January 2013
Antiaromatic bisindeno-[n]thienoacenes with small singlet biradical characters: syntheses, structures and chain length dependent physical properties Shi, Xueliang; Burrezo, Paula Mayorga; Lee, Sangsu Chem. Sci., Vol. 5, Issue 11 https://doi.org/10.1039/c4sc01769b	journal	January 2014
Dithienonaphthothiadiazole semiconductors: synthesis, properties, and application to ambipolar field effect transistors Shuai, Q.; Black, H. T.; Dadvand, A. Journal of Materials Chemistry C, Vol. 2, Issue 20 https://doi.org/10.1039/c4tc00094c	journal	January 2014
Substituent effect on the crystal packing and electronic coupling of tetrabenzocoronenes: a structure–property correlation Kuo, Chi-Hsien; Huang, Ding-Chi; Peng, Wei-Tao Journal of Materials Chemistry C, Vol. 2, Issue 20 https://doi.org/10.1039/c4tc00296b	journal	January 2014
Asymmetric fused thiophenes for field-effect transistors: crystal structure–film microstructure–transistor performance correlations Chen, Ming-Chou; Vegiraju, Sureshraju; Huang, Chi-Ming J. Mater. Chem. C, Vol. 2, Issue 42 https://doi.org/10.1039/c4tc01454e	journal	January 2014
Enhancement of the p-channel performance of sulfur-bridged annulene through a donor–acceptor co-crystal approach Zhang, Jing; Zhao, Guangyao; Qin, Yunke J. Mater. Chem. C, Vol. 2, Issue 42 https://doi.org/10.1039/c4tc01876a	journal	January 2014
Rationally designed donor–acceptor scheme based molecules for applications in opto-electronic devices Subash Sundar, T.; Sen, R.; Johari, P. Physical Chemistry Chemical Physics, Vol. 18, Issue 13 https://doi.org/10.1039/c6cp00367b	journal	January 2016
The prediction of hole mobility in organic semiconductors and its calibration based on the grain-boundary effect Park, Jin Woo; Lee, Kyu Il; Choi, Youn-Suk Physical Chemistry Chemical Physics, Vol. 18, Issue 31 https://doi.org/10.1039/c6cp02993k	journal	January 2016
Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives Ruzié, Christian; Karpinska, Jolanta; Laurent, Anne Journal of Materials Chemistry C, Vol. 4, Issue 22 https://doi.org/10.1039/c6tc01409g	journal	January 2016
Role of intermolecular charge delocalization and its dimensionality in efficient band-like electron transport in crystalline 2,5-difluoro-7,7,8,8-tetracyanoquinodimethane (F ₂ -TCNQ) Sosorev, Andrey Yu. Physical Chemistry Chemical Physics, Vol. 19, Issue 37 https://doi.org/10.1039/c7cp04357k	journal	January 2017
Organic semiconductor crystals Wang, Chengliang; Dong, Huanli; Jiang, Lang Chemical Society Reviews, Vol. 47, Issue 2 https://doi.org/10.1039/c7cs00490g	journal	January 2018
Isomerism effect on the photovoltaic properties of benzotrithiophene-based hole-transporting materials García-Benito, Inés; Zimmermann, Iwan; Urieta-Mora, Javier Journal of Materials Chemistry A, Vol. 5, Issue 18 https://doi.org/10.1039/c7ta00997f	journal	January 2017
Hole transporting materials based on benzodithiophene and dithienopyrrole cores for efficient perovskite solar cells Sandoval-Torrientes, R.; Zimmermann, I.; Calbo, J. Journal of Materials Chemistry A, Vol. 6, Issue 14 https://doi.org/10.1039/c7ta11314e	journal	January 2018
Solution-grown unidirectionally oriented crystalline thin films of a U-shaped thienoacene-based semiconductor for high-performance organic field-effect transistors Mori, Tatsuya; Oyama, Tatsuya; Komiyama, Hideaki Journal of Materials Chemistry C, Vol. 5, Issue 24 https://doi.org/10.1039/c7tc01836c	journal	January 2017
Luminescence-/morphology-modulation of organic microcrystals by a protonation process Li, Zhi-Zhou; Wang, Xue-Dong; Liao, Liang-Sheng Journal of Materials Chemistry C, Vol. 5, Issue 27 https://doi.org/10.1039/c7tc02013a	journal	January 2017
The influence of external electric fields on charge reorganization energy in organic semiconductors Huang, Weicong; Shi, Hu; Liu, Hongguang Chemical Communications, Vol. 55, Issue 16 https://doi.org/10.1039/c8cc09680e	journal	January 2019
Intrinsic charge-mobility in benzothieno[3,2- b ][1]benzothiophene (BTBT) organic semiconductors is enhanced with long alkyl side-chains Alkan, M.; Yavuz, I. Physical Chemistry Chemical Physics, Vol. 20, Issue 23 https://doi.org/10.1039/c8cp01640b	journal	January 2018
Benchmarking DFT approaches for the calculation of polarizability inputs for refractive index predictions in organic polymers Afzal, Mohammad Atif Faiz; Hachmann, Johannes Physical Chemistry Chemical Physics, Vol. 21, Issue 8 https://doi.org/10.1039/c8cp05492d	journal	January 2019
Impact of morphology, side-chains, and crystallinity on charge-transport properties of π-extended double helicenes Yavuz, Ilhan; Lin, Janice B.; Houk, K. N. Physical Chemistry Chemical Physics, Vol. 21, Issue 2 https://doi.org/10.1039/c8cp06982d	journal	January 2019
Novel adamantane-based hole transport materials for perovskite solar cells: a computational approach Gapol, Maebienne Anjelica B.; Kim, Dong Hee Physical Chemistry Chemical Physics, Vol. 21, Issue 7 https://doi.org/10.1039/c8cp07515h	journal	January 2019
New π-extended catecholato complexes of Pt( ii ) and Pd( ii ) containing a benzothienobenzothiophene (BTBT) moiety: synthesis, electrochemical behavior and charge transfer properties Tahara, Keishiro; Ashihara, Yuya; Higashino, Toshiki Dalton Transactions, Vol. 48, Issue 21 https://doi.org/10.1039/c8dt05057k	journal	January 2019
A quantitative structure–property study of reorganization energy for known p-type organic semiconductors Atahan-Evrenk, Sule RSC Advances, Vol. 8, Issue 70 https://doi.org/10.1039/c8ra07866a	journal	January 2018
Experimental and theoretical evidence of a supercritical-like transition in an organic semiconductor presenting colossal uniaxial negative thermal expansion van der Lee, Arie; Roche, Gilles H.; Wantz, Guillaume Chemical Science, Vol. 9, Issue 16 https://doi.org/10.1039/c8sc00159f	journal	January 2018
Low surface energy interface-derived low-temperature recrystallization behavior of organic thin films for boosting carrier mobility Wang, Shuya; Wei, Zhan; Yang, Yahan Journal of Materials Chemistry C, Vol. 7, Issue 44 https://doi.org/10.1039/c9tc05043d	journal	January 2019
Surface-guided polymorphism control of titanyl phthalocyanine single crystals Yoon, Youngkwan; Koo, Jin Young; Oh, Jongwon Inorganic Chemistry Frontiers, Vol. 7, Issue 11 https://doi.org/10.1039/d0qi00228c	journal	January 2020
Exciton transport in thin-film cyanine dye J-aggregates Valleau, Stéphanie; Saikin, Semion K.; Yung, Man-Hong The Journal of Chemical Physics, Vol. 137, Issue 3 https://doi.org/10.1063/1.4732122	journal	July 2012
Simulated evolution of fluorophores for light emitting diodes Shu, Yinan; Levine, Benjamin G. The Journal of Chemical Physics, Vol. 142, Issue 10 https://doi.org/10.1063/1.4914294	journal	March 2015
Tracking speed bumps in organic field-effect transistors via pump-probe Kelvin-probe force microscopy Murawski, J.; Mönch, T.; Milde, P. Journal of Applied Physics, Vol. 118, Issue 24 https://doi.org/10.1063/1.4938529	journal	December 2015
Combining first-principles and data modeling for the accurate prediction of the refractive index of organic polymers Afzal, Mohammad Atif Faiz; Cheng, Chong; Hachmann, Johannes The Journal of Chemical Physics, Vol. 148, Issue 24 https://doi.org/10.1063/1.5007873	journal	June 2018
Photophysical features and semiconducting properties of propeller-shaped oligo(styryl)benzenes Moral, Mónica; Domínguez, Rocío; Fernández-Liencres, M. Paz The Journal of Chemical Physics, Vol. 150, Issue 6 https://doi.org/10.1063/1.5079935	journal	February 2019
MOlecular MAterials Property Prediction Package (MOMAP) 1.0: a software package for predicting the luminescent properties and mobility of organic functional materials Niu, Yingli; Li, Wenqiang; Peng, Qian Molecular Physics, Vol. 116, Issue 7-8 https://doi.org/10.1080/00268976.2017.1402966	journal	February 2018
Novel 5-(4-alkoxyphenyl)thieno[3,2- b ]thiophene-2-carboxylate esters: Highly efficient synthesis and mesogenic evaluation of a new class of materials exhibiting the smectic C phase Tietz, Jonathan I.; Mastriana, James R.; Sampson, Paul Liquid Crystals, Vol. 39, Issue 5 https://doi.org/10.1080/02678292.2012.657698	journal	May 2012
Faster quantum chemistry simulation on fault-tolerant quantum computers Cody Jones, N.; Whitfield, James D.; McMahon, Peter L. New Journal of Physics, Vol. 14, Issue 11 https://doi.org/10.1088/1367-2630/14/11/115023	journal	November 2012
Nonadiabatic molecular dynamics simulation for carrier transport in a pentathiophene butyric acid monolayer Ren, Junfeng; Vukmirović, Nenad; Wang, Lin-Wang Physical Review B, Vol. 87, Issue 20 https://doi.org/10.1103/physrevb.87.205117	journal	May 2013
Charge carrier mobility in systems with local electron-phonon interaction Prodanović, Nikola; Vukmirović, Nenad Physical Review B, Vol. 99, Issue 10 https://doi.org/10.1103/physrevb.99.104304	journal	March 2019
Recent trends in crystal engineering of high-mobility materials for organic electronics Yassar, Abderrahim Polymer Science Series C, Vol. 56, Issue 1 https://doi.org/10.1134/s1811238214010111	journal	July 2014
Ultra-high mobility transparent organic thin film transistors grown by an off-centre spin-coating method Dennis, Nordlund,; Zhenan, Bao,; F., Toney, Michael The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/8f2z-z037	text	January 2014
Structure Prediction Drives Materials Discovery Oganov, Artem; Pickard, Christopher; Zhu, Qiang Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.39313	text	January 2019
High operational and environmental stability of high-mobility conjugated polymer field-effect transistors through the use of molecular additives. Nikolka, Mark; Nasrallah, Iyad; Rose, Bradley Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.6390	text	January 2017
Combining First-Principles and Data Modeling for the Accurate Prediction of the Refractive Index of Organic Polymers Afzal, Mohammad Atif Faiz; Cheng, Chong; Hachmann, Johannes Theoretical and Computational Chemistry https://doi.org/10.26434/chemrxiv.5446564.v1	journal	September 2017
Benchmarking DFT Approaches for the Calculation of Polarizability Inputs for Refractive Index Predictions in Organic Polymers Afzal, Mohammad Atif Faiz; Hachmann, Johannes Materials Science https://doi.org/10.26434/chemrxiv.6934343.v2	journal	January 2019
Moderate doping leads to high performance of semiconductor/insulator polymer blend transistors Lu, G.; Blakesley, J.; Himmelberger, S. Deutsches Elektronen-Synchrotron, DESY, Hamburg https://doi.org/10.3204/phppubdb-26157	text	January 2013
Recent Trends in Crystal Engineering of High-Mobility Materials for Organic Electronics Yassar, Abderrahim Высокомолекулярные соединения С, Vol. 56, Issue 1 https://doi.org/10.7868/s2308114714010117	journal	January 2014

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