Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives

Ogden, William A.; Ghosh, Soumen; Bruzek, Matthew J.; McGarry, Kathryn A.; Balhorn, Luke; Young, Jr., Victor; Purvis, Lafe J.; Wegwerth, Sarah E.; Zhang, Zhuoran; Serratore, Nicholas A.; Cramer, Christopher J.; Gagliardi, Laura; Douglas, Christopher J.

doi:10.1021/acs.cgd.6b01497

Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives

Journal Article · Wed Dec 28 23:00:00 EST 2016 · Crystal Growth and Design

DOI:https://doi.org/10.1021/acs.cgd.6b01497· OSTI ID:1534432

Ogden, William A. ^[1]; Ghosh, Soumen ^[2]; Bruzek, Matthew J. ^[2]; McGarry, Kathryn A. ^[2]; Balhorn, Luke ^[2]; Young, Jr., Victor ^[2]; Purvis, Lafe J. ^[2]; Wegwerth, Sarah E. ^[2]; Zhang, Zhuoran ^[2]; Serratore, Nicholas A. ^[2]; ^[2]; ^[2]; ^[2]

Univ. of Minnesota, Minneapolis, MN (United States); DOE/OSTI
Univ. of Minnesota, Minneapolis, MN (United States)

Through a close examination of the intermolecular interactions of rubrene (1a) and select derivatives (1b–1p), a clearer understanding of why certain fluorinated rubrene derivatives pack with planar tetracene backbones has been achieved. In this study we synthesized, crystallized, and determined the packing structure of new rubrene derivatives (1h–p). Previously, we proposed that introducing electron-withdrawing CF3 substituents induced planarity by reducing intramolecular repulsion between the peripheral aryl groups (1e–g). However, we found that in most cases, further increasing the fluorine content of rubrene lead to twisted tetracene backbones in the solid state. To understand how rubrene (1a) and its derivatives (1b–p) pack in the solid state, we (re)examined the crystal structures through a systematic study of the close contacts. We found that planar tetracene cores occur when close contacts organize to produce an S symmetry element about a given rubrene molecule. Here, we report the first instance of rubrene derivatives (1l and 1n) that pack in a two-dimensional brick motif. The prospects for new rubrene derivatives in semiconductors were estimated by calculating the reorganization energies of the monomers and transfer integrals of the dimers we observed. Our work allows for the rational design and improved crystal engineering of new rubrene derivatives.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Minnesota, Minneapolis, MN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; USDOE Office of Science (SC), Advanced Scientific Computing Research (ASCR). Scientific Discovery through Advanced Computing (SciDAC); National Science Foundation (NSF)

Grant/Contract Number:: SC0008666

OSTI ID:: 1534432

Journal Information:: Crystal Growth and Design, Journal Name: Crystal Growth and Design Journal Issue: 2 Vol. 17; ISSN 1528-7483

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (83)

Transport Properties in the Rubrene Crystal: Electronic Coupling and Vibrational Reorganization Energy da Silva Filho, D. A.; Kim, E. -G.; Brédas, J. -L. Advanced Materials, Vol. 17, Issue 8 https://doi.org/10.1002/adma.200401866	journal	April 2005
n-Type Organic Semiconductors in Organic Electronics Anthony, John E.; Facchetti, Antonio; Heeney, Martin Advanced Materials, Vol. 22, Issue 34, p. 3876-3892 https://doi.org/10.1002/adma.200903628	journal	August 2010
Connecting Molecular Structure and Exciton Diffusion Length in Rubrene Derivatives Mullenbach, Tyler K.; McGarry, Kathryn A.; Luhman, Wade A. Advanced Materials, Vol. 25, Issue 27 https://doi.org/10.1002/adma.201300641	journal	June 2013
Organic Synthesis—Where now? Seebach, Dieter Angewandte Chemie International Edition in English, Vol. 29, Issue 11 https://doi.org/10.1002/anie.199013201	journal	November 1990
Arene—Arene Interactions: Electrostatic or Charge Transfer? Hunter, Christopher A. Angewandte Chemie International Edition in English, Vol. 32, Issue 11 https://doi.org/10.1002/anie.199315841	journal	November 1993
Polar Interactions between Stackedπ Systems in Fluorinated 1,8-Diarylnaphthalenes: Importance of Quadrupole Moments in Molecular Recognition Cozzi, Franco; Ponzini, Francesco; Annunziata, Rita Angewandte Chemie International Edition in English, Vol. 34, Issue 9 https://doi.org/10.1002/anie.199510191	journal	May 1995
Crystal Engineering of Dual Channel p/n Organic Semiconductors by Complementary Hydrogen Bonding Black, Hayden T.; Perepichka, Dmitrii F. Angewandte Chemie International Edition, Vol. 53, Issue 8 https://doi.org/10.1002/anie.201310902	journal	February 2014
Rubrenes: Planar and Twisted Paraskar, Abhimanyu S.; Reddy, A. Ravikumar; Patra, Asit Chemistry - A European Journal, Vol. 14, Issue 34 https://doi.org/10.1002/chem.200800802	journal	October 2008
The Rubrenic Synthesis: The Delicate Equilibrium between Tetracene and Cyclobutene Braga, Daniele; Jaafari, Abdelhafid; Miozzo, Luciano European Journal of Organic Chemistry, Vol. 2011, Issue 22 https://doi.org/10.1002/ejoc.201100033	journal	May 2011
Chemistry with ADF te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J. Journal of Computational Chemistry, Vol. 22, Issue 9, p. 931-967 https://doi.org/10.1002/jcc.1056	journal	January 2001
An approximate method for calculating transfer integrals based on the ZINDO Hamiltonian Kirkpatrick, James International Journal of Quantum Chemistry, Vol. 108, Issue 1 https://doi.org/10.1002/qua.21378	journal	January 2007
Understanding of Noncovalent Interactions Involving Organic Fluorine Panini, Piyush; Chopra, Deepak Hydrogen Bonded Supramolecular Structures. Lecture Notes in Chemistry https://doi.org/10.1007/978-3-662-45756-6_2	book	January 2015
The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Zhao, Yan; Truhlar, Donald G. Theoretical Chemistry Accounts, Vol. 120, Issue 1-3 https://doi.org/10.1007/s00214-007-0310-x	journal	July 2007
Theoretical evaluation of the nature and strength of the F···F intermolecular interactions present in fluorinated hydrocarbons Osuna, Reyes Malavé; Hernández, Victor; Navarrete, Juan T. López Theoretical Chemistry Accounts, Vol. 128, Issue 4-6 https://doi.org/10.1007/s00214-010-0830-7	journal	October 2010
C-F...π, F...H, and F...F intermolecular interactions and F-aggregation: Role in crystal engineering of fluoroorganic compounds Rybalova, T. V.; Bagryanskaya, I. Yu. Journal of Structural Chemistry, Vol. 50, Issue 4 https://doi.org/10.1007/s10947-009-0113-0	journal	August 2009
Quantitative crystal structure analysis of fluorinated porphyrins Soman, Rahul; Sujatha, Subramaniam; Arunkumar, Chellaiah Journal of Fluorine Chemistry, Vol. 163 https://doi.org/10.1016/j.jfluchem.2014.04.002	journal	July 2014
Role of Crystal Packing and Weak Intermolecular Interactions in the Solid State Fluorescence of N -Methylpyrazoline Derivatives Kupcewicz, Bogumiła; Małecka, Magdalena Crystal Growth & Design, Vol. 15, Issue 8 https://doi.org/10.1021/acs.cgd.5b00512	journal	June 2015
It Isn’t, It Is: The C–H···X (X = O, N, F, Cl) Interaction Really Is Significant in Crystal Packing Taylor, Robin Crystal Growth & Design, Vol. 16, Issue 8 https://doi.org/10.1021/acs.cgd.6b00736	journal	July 2016
Crystalline Alloys of Organic Donors and Acceptors Based on TIPS-Pentacene Sherman, Jes B.; Moncino, Kai; Baruah, Tunna The Journal of Physical Chemistry C, Vol. 119, Issue 36 https://doi.org/10.1021/acs.jpcc.5b06363	journal	August 2015
How Realistic Are Interactions Involving Organic Fluorine in Crystal Engineering? Insights from Packing Features in Substituted Isoquinolines ^† Choudhury, Angshuman Roy; Guru Row, Tayur N. Crystal Growth & Design, Vol. 4, Issue 1 https://doi.org/10.1021/cg034137n	journal	January 2004
Dibenzothiophene Derivatives: From Herringbone to Lamellar Packing Motif Wang, Chengliang; Dong, Huanli; Li, Hongxiang Crystal Growth & Design, Vol. 10, Issue 9 https://doi.org/10.1021/cg100863q	journal	August 2010
Is Organic Fluorine Really “Not” Polarizable? Chopra, Deepak Crystal Growth & Design, Vol. 12, Issue 2 https://doi.org/10.1021/cg201498u	journal	January 2012
Rubrene Polymorphs and Derivatives: The Effect of Chemical Modification on the Crystal Structure Bergantin, Stefano; Moret, Massimo Crystal Growth & Design, Vol. 12, Issue 12 https://doi.org/10.1021/cg301130n	journal	November 2012
Structural Motifs in Enantiopure Halogenated Aryl Benzyl Sulfoxides: Effect of Fluorine Substitution Capozzi, Maria Annunziata M.; Capitelli, Francesco; Cardellicchio, Cosimo Crystal Growth & Design, Vol. 14, Issue 11 https://doi.org/10.1021/cg5006117	journal	September 2014
Characterization of New Rubrene Analogues with Heteroaryl Substituents Mamada, Masashi; Katagiri, Hiroshi; Sakanoue, Tomo Crystal Growth & Design, Vol. 15, Issue 1 https://doi.org/10.1021/cg501519a	journal	December 2014
Influence of Fluorine Substitution on the Crystal Packing of N -Phenylmaleimides and Corresponding Phthalimides Schwarzer, Anke; Weber, Edwin Crystal Growth & Design, Vol. 8, Issue 8 https://doi.org/10.1021/cg7011638	journal	June 2008
Rubrene-Based Single-Crystal Organic Semiconductors: Synthesis, Electronic Structure, and Charge-Transport Properties McGarry, Kathryn A.; Xie, Wei; Sutton, Christopher Chemistry of Materials, Vol. 25, Issue 11 https://doi.org/10.1021/cm400736s	journal	May 2013
Recent Highlights and Perspectives on Acene Based Molecules and Materials Ye, Qun; Chi, Chunyan Chemistry of Materials, Vol. 26, Issue 14 https://doi.org/10.1021/cm501536p	journal	July 2014
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
Functionalized Acenes and Heteroacenes for Organic Electronics Anthony, John E. Chemical Reviews, Vol. 106, Issue 12 https://doi.org/10.1021/cr050966z	journal	December 2006
Relevance of Weak Hydrogen Bonds in the Conformation of Organic Compounds and Bioconjugates: Evidence from Recent Experimental Data and High-Level ab Initio MO Calculations Takahashi, Osamu; Kohno, Yuji; Nishio, Motohiro Chemical Reviews, Vol. 110, Issue 10 https://doi.org/10.1021/cr100072x	journal	October 2010
Electronic Structure Study of Singlet Fission in Tetracene Derivatives Casanova, David Journal of Chemical Theory and Computation, Vol. 10, Issue 1 https://doi.org/10.1021/ct4007635	journal	November 2013
Polar/.pi. interactions between stacked aryls in 1,8-diarylnaphthalenes Cozzi, Franco; Cinquini, Mauro; Annunziata, Rita Journal of the American Chemical Society, Vol. 114, Issue 14 https://doi.org/10.1021/ja00040a036	journal	July 1992
Dominance of polar/.pi. over charge-transfer effects in stacked phenyl interactions Cozzi, Franco; Cinquini, Mauro; Annuziata, Rita Journal of the American Chemical Society, Vol. 115, Issue 12 https://doi.org/10.1021/ja00065a069	journal	June 1993
The nature of .pi.-.pi. interactions Hunter, Christopher A.; Sanders, Jeremy K. M. Journal of the American Chemical Society, Vol. 112, Issue 14 https://doi.org/10.1021/ja00170a016	journal	July 1990
Spiroannelation of enol ethers of cyclic 1,3-diketones. Simple stereospecific synthesis of .beta.-vetivone Stork, Gilbert.; Danheiser, Rick L.; Ganem, Bruce. Journal of the American Chemical Society, Vol. 95, Issue 10 https://doi.org/10.1021/ja00791a074	journal	May 1973
Functionalized Pentacene: Improved Electronic Properties from Control of Solid-State Order Anthony, John E.; Brooks, James S.; Eaton, David L. Journal of the American Chemical Society, Vol. 123, Issue 38 https://doi.org/10.1021/ja0162459	journal	September 2001
Perfluoropentacene: High-Performance p−n Junctions and Complementary Circuits with Pentacene Sakamoto, Youichi; Suzuki, Toshiyasu; Kobayashi, Masafumi Journal of the American Chemical Society, Vol. 126, Issue 26 https://doi.org/10.1021/ja0476258	journal	July 2004
Functionalized Higher Acenes: Hexacene and Heptacene Payne, Marcia M.; Parkin, Sean R.; Anthony, John E. Journal of the American Chemical Society, Vol. 127, Issue 22 https://doi.org/10.1021/ja051798v	journal	June 2005
High-Performance Organic Semiconductors: Asymmetric Linear Acenes Containing Sulphur Tang, Ming L.; Okamoto, Toshihiro; Bao, Zhenan Journal of the American Chemical Society, Vol. 128, Issue 50 https://doi.org/10.1021/ja066824j	journal	December 2006
Combining Electron-Neutral Building Blocks with Intramolecular “Conformational Locks” Affords Stable, High-Mobility P- and N-Channel Polymer Semiconductors Huang, Hui; Chen, Zhihua; Ortiz, Rocio Ponce Journal of the American Chemical Society, Vol. 134, Issue 26 https://doi.org/10.1021/ja303401s	journal	June 2012
Impact of Regiochemistry and Isoelectronic Bridgehead Substitution on the Molecular Shape and Bulk Organization of Narrow Bandgap Chromophores Welch, Gregory C.; Bakus, Ronald C.; Teat, Simon J. Journal of the American Chemical Society, Vol. 135, Issue 6 https://doi.org/10.1021/ja310694t	journal	January 2013
Integrated Materials Design of Organic Semiconductors for Field-Effect Transistors Mei, Jianguo; Diao, Ying; Appleton, Anthony L. Journal of the American Chemical Society, Vol. 135, Issue 18 https://doi.org/10.1021/ja400881n	journal	April 2013
Crystal Engineering: From Molecule to Crystal Desiraju, Gautam R. Journal of the American Chemical Society, Vol. 135, Issue 27 https://doi.org/10.1021/ja403264c	journal	June 2013
Impact of Molecular Packing on Electronic Polarization in Organic Crystals: The Case of Pentacene vs TIPS-Pentacene Ryno, Sean M.; Risko, Chad; Brédas, Jean-Luc Journal of the American Chemical Society, Vol. 136, Issue 17 https://doi.org/10.1021/ja501725s	journal	April 2014
Two-Dimensional π-Expanded Quinoidal Terthiophenes Terminated with Dicyanomethylenes as n-Type Semiconductors for High-Performance Organic Thin-Film Transistors Zhang, Cheng; Zang, Yaping; Gann, Eliot Journal of the American Chemical Society, Vol. 136, Issue 46 https://doi.org/10.1021/ja510003y	journal	November 2014
Ambipolar, High Performance, Acene-Based Organic Thin Film Transistors Tang, Ming L.; Reichardt, Anna D.; Miyaki, Nobuyuki Journal of the American Chemical Society, Vol. 130, Issue 19 https://doi.org/10.1021/ja8005918	journal	April 2008
Chlorination: A General Route toward Electron Transport in Organic Semiconductors Tang, Ming Lee; Oh, Joon Hak; Reichardt, Anna Devi Journal of the American Chemical Society, Vol. 131, Issue 10 https://doi.org/10.1021/ja809045s	journal	March 2009
Correlating Carrier Type with Frontier Molecular Orbital Energy Levels in Organic Thin Film Transistors of Functionalized Acene Derivatives Tang, Ming L.; Reichardt, Anna D.; Wei, Peng Journal of the American Chemical Society, Vol. 131, Issue 14 https://doi.org/10.1021/ja809659b	journal	April 2009
Conformational Order in Aggregates of Conjugated Polymers Jackson, Nicholas E.; Kohlstedt, Kevin L.; Savoie, Brett M. Journal of the American Chemical Society, Vol. 137, Issue 19 https://doi.org/10.1021/jacs.5b00493	journal	May 2015
Rubrene: The Interplay between Intramolecular and Intermolecular Interactions Determines the Planarization of Its Tetracene Core in the Solid State Sutton, Christopher; Marshall, Michael S.; Sherrill, C. David Journal of the American Chemical Society, Vol. 137, Issue 27 https://doi.org/10.1021/jacs.5b04066	journal	July 2015
Fine-Tuning of Crystal Packing and Charge Transport Properties of BDOPV Derivatives through Fluorine Substitution Dou, Jin-Hu; Zheng, Yu-Qing; Yao, Ze-Fan Journal of the American Chemical Society, Vol. 137, Issue 50 https://doi.org/10.1021/jacs.5b11114	journal	December 2015
Regioselective synthesis of substituted rubrenes Dodge, Jeffrey A.; Bain, J. D.; Chamberlin, A. Richard The Journal of Organic Chemistry, Vol. 55, Issue 13 https://doi.org/10.1021/jo00300a043	journal	June 1990
Noncovalent Intramolecular Interactions in the Monomers and Oligomers of the Acceptor and Donor Type of Low Band Gap Conducting Polymers Özen, Alimet Sema; Atilgan, Canan; Sonmez, Gursel The Journal of Physical Chemistry C, Vol. 111, Issue 44 https://doi.org/10.1021/jp074380n	journal	November 2007
High-Mobility Transistors Based on Single Crystals of Isotopically Substituted Rubrene- d ₂₈ Xie, Wei; McGarry, Kathryn A.; Liu, Feilong The Journal of Physical Chemistry C, Vol. 117, Issue 22 https://doi.org/10.1021/jp402250v	journal	May 2013
Synthesis, Solid State Properties, and Semiconductor Measurements of 5,6,11,12-Tetrachlorotetracene Yagodkin, Elisey; Xia, Yu; Kalihari, Vivek The Journal of Physical Chemistry C, Vol. 113, Issue 37 https://doi.org/10.1021/jp904476z	journal	August 2009
Intermolecular Nonbonded Contact Distances in Organic Crystal Structures: Comparison with Distances Expected from van der Waals Radii Rowland, R. Scott; Taylor, Robin The Journal of Physical Chemistry, Vol. 100, Issue 18 https://doi.org/10.1021/jp953141+	journal	January 1996
Utilizing Carbon Nanotube Electrodes to Improve Charge Injection and Transport in Bis(trifluoromethyl)-dimethyl-rubrene Ambipolar Single Crystal Transistors Xie, Wei; Prabhumirashi, Pradyumna L.; Nakayama, Yasuo ACS Nano, Vol. 7, Issue 11 https://doi.org/10.1021/nn4045694	journal	October 2013
Tetracene Derivatives as Potential Red Emitters for Organic LEDs Odom, Susan A.; Parkin, Sean R.; Anthony, John E. Organic Letters, Vol. 5, Issue 23 https://doi.org/10.1021/ol035415e	journal	November 2003
Fluorine in crystal engineering—“the little atom that could” Reichenbächer, Katharina; Süss, Heike I.; Hulliger, Jürg Chem. Soc. Rev., Vol. 34, Issue 1 https://doi.org/10.1039/B406892K	journal	January 2005
Rubrene micro-crystals from solution routes: their crystallography, morphology and optical properties Huang, Liwei; Liao, Qing; Shi, Qiang J. Mater. Chem., Vol. 20, Issue 1 https://doi.org/10.1039/B914334C	journal	January 2010
Which intermolecular interactions have a significant influence on crystal packing? Taylor, Robin CrystEngComm, Vol. 16, Issue 30 https://doi.org/10.1039/C4CE00452C	journal	January 2014
Charge mobility anisotropy of functionalized pentacenes in organic field effect transistors fabricated by solution processing Wade, Jessica; Steiner, Florian; Niedzialek, Dorota J. Mater. Chem. C, Vol. 2, Issue 47 https://doi.org/10.1039/C4TC01353K	journal	January 2014
Synthesis, electrochemical properties, and crystal packing of perfluororubrene Zhang, Zhuoran; Ogden, William A.; Young, Victor G. Chemical Communications, Vol. 52, Issue 52 https://doi.org/10.1039/C6CC03259A	journal	January 2016
Synthesis of fluorophenyl derivatives of iron, molybdenum and tungsten via B(C6F5)3 and unusual carbon–fluorine bond reactions Chernega, Alexander N.; Graham, Andrew J.; Green, Malcolm L. H. Journal of the Chemical Society, Dalton Transactions, Issue 13 https://doi.org/10.1039/a700925i	journal	January 1997
Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections Chai, Jeng-Da; Head-Gordon, Martin Physical Chemistry Chemical Physics, Vol. 10, Issue 44 https://doi.org/10.1039/b810189b	journal	January 2008
CH/π hydrogen bonds in organic and organometallic chemistry Nishio, Motohiro; Umezawa, Yoji; Honda, Kazumasa CrystEngComm, Vol. 11, Issue 9 https://doi.org/10.1039/b902318f	journal	January 2009
Role of organic fluorine in crystal engineering Chopra, Deepak; Row, Tayur N. Guru CrystEngComm, Vol. 13, Issue 7 https://doi.org/10.1039/c0ce00538j	journal	January 2011
Quantitative insights into energy contributions of intermolecular interactions in fluorine and trifluoromethyl substituted isomeric N-phenylacetamides and N-methylbenzamides Panini, Piyush; Chopra, Deepak CrystEngComm, Vol. 15, Issue 18 https://doi.org/10.1039/c3ce40111a	journal	January 2013
Connecting molecule oxidation to single crystal structural and charge transport properties in rubrene derivatives Uttiya, S.; Miozzo, L.; Fumagalli, E. M. J. Mater. Chem. C, Vol. 2, Issue 21 https://doi.org/10.1039/c3tc32527j	journal	January 2014
Charge transport in columnar stacked triphenylenes: Effects of conformational fluctuations on charge transfer integrals and site energies Senthilkumar, K.; Grozema, F. C.; Bickelhaupt, F. M. The Journal of Chemical Physics, Vol. 119, Issue 18 https://doi.org/10.1063/1.1615476	journal	November 2003
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
Very high-mobility organic single-crystal transistors with in-crystal conduction channels Takeya, J.; Yamagishi, M.; Tominari, Y. Applied Physics Letters, Vol. 90, Issue 10 https://doi.org/10.1063/1.2711393	journal	March 2007
Systematic optimization of long-range corrected hybrid density functionals Chai, Jeng-Da; Head-Gordon, Martin The Journal of Chemical Physics, Vol. 128, Issue 8 https://doi.org/10.1063/1.2834918	journal	February 2008
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Toward reliable density functional methods without adjustable parameters: The PBE0 model Adamo, Carlo; Barone, Vincenzo The Journal of Chemical Physics, Vol. 110, Issue 13 https://doi.org/10.1063/1.478522	journal	April 1999
Preparation of 6,11-Dihydroxy-5,12-tetracenedione Yagodkin, Elisey; McGarry, Kathryn A.; Douglas, Christopher J. Organic Preparations and Procedures International, Vol. 43, Issue 4 https://doi.org/10.1080/00304948.2011.594006	journal	January 2011
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
Intrinsic Charge Transport on the Surface of Organic Semiconductors Podzorov, V.; Menard, E.; Borissov, A. Physical Review Letters, Vol. 93, Issue 8, Article No. 086602 https://doi.org/10.1103/PhysRevLett.93.086602	journal	August 2004
Novel tools for visualizing and exploring intermolecular interactions in molecular crystals McKinnon, Joshua J.; Spackman, Mark A.; Mitchell, Anthony S. Acta Crystallographica Section B Structural Science, Vol. 60, Issue 6 https://doi.org/10.1107/S0108768104020300	journal	November 2004
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
Interaction between stacked aryl groups in 1,8-diarylnaphthalenes: Dominance of polar/π over charge-transfer effects Cozzi, F.; Siegel, J. S. Pure and Applied Chemistry, Vol. 67, Issue 5 https://doi.org/10.1351/pac199567050683	journal	January 1995
Crystal design using multipolar electrostatic interactions: A concept study for organic electronics Kirsch, Peer; Tong, Qiong; Untenecker, Harald Beilstein Journal of Organic Chemistry, Vol. 9 https://doi.org/10.3762/bjoc.9.272	journal	January 2013

Cited By (2)

Modulating the Electronic and Solid‐State Structure of Organic Semiconductors by Site‐Specific Substitution: The Case of Tetrafluoropentacenes Geiger, Thomas; Schundelmeier, Simon; Hummel, Thorsten Chemistry – A European Journal, Vol. 26, Issue 15 https://doi.org/10.1002/chem.201905843	journal	March 2020
A 2-D π–π dimer model system to investigate structure-charge transfer relationships in rubrene Chung, Sherlyn J.; McHugh, Callum J.; Calvo-Castro, Jesus Journal of Materials Chemistry C, Vol. 7, Issue 7 https://doi.org/10.1039/c8tc06412a	journal	January 2019

Figures / Tables (25)

Similar Records

Related Subjects

36 MATERIALS SCIENCE
Chemistry
Crystal structure
Crystallography
Layered materials
Materials science
Molecular interactions
Oligomers
Reaction products

CCDC 1509405: Experimental Crystal Structure Determination Ogden, William A.; Ghosh, Soumen; Bruzek, Matthew J. https://doi.org/10.5517/ccdc.csd.cc1mnnhf The current record is supplemented by this dataset	dataset	January 2017
CCDC 1509406: Experimental Crystal Structure Determination Ogden, William A.; Ghosh, Soumen; Bruzek, Matthew J. https://doi.org/10.5517/ccdc.csd.cc1mnnjg The current record is supplemented by this dataset	dataset	January 2017
CCDC 1509407: Experimental Crystal Structure Determination Ogden, William A.; Ghosh, Soumen; Bruzek, Matthew J. https://doi.org/10.5517/ccdc.csd.cc1mnnkh The current record is supplemented by this dataset	dataset	January 2017
CCDC 1509408: Experimental Crystal Structure Determination Ogden, William A.; Ghosh, Soumen; Bruzek, Matthew J. https://doi.org/10.5517/ccdc.csd.cc1mnnlj The current record is supplemented by this dataset	dataset	January 2017
CCDC 1509409: Experimental Crystal Structure Determination Ogden, William A.; Ghosh, Soumen; Bruzek, Matthew J. https://doi.org/10.5517/ccdc.csd.cc1mnnmk The current record is supplemented by this dataset	dataset	January 2017
CCDC 1509410: Experimental Crystal Structure Determination Ogden, William A.; Ghosh, Soumen; Bruzek, Matthew J. https://doi.org/10.5517/ccdc.csd.cc1mnnnl The current record is supplemented by this dataset	dataset	January 2017
CCDC 1509411: Experimental Crystal Structure Determination Ogden, William A.; Ghosh, Soumen; Bruzek, Matthew J. https://doi.org/10.5517/ccdc.csd.cc1mnnpm The current record is supplemented by this dataset	dataset	January 2017
CCDC 1509412: Experimental Crystal Structure Determination Ogden, William A.; Ghosh, Soumen; Bruzek, Matthew J. https://doi.org/10.5517/ccdc.csd.cc1mnnqn The current record is supplemented by this dataset	dataset	January 2017

Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives

Citation Formats

References (83)

Cited By (2)

Linked Research (8)

Figures / Tables (25)

Similar Records

Related Subjects