Highly organized smectic-like packing in vapor-deposited glasses of a liquid crystal

Gujral, Ankit; Gomez, Jaritza; Jiang, Jing; Huang, Chengbin; O’Hara, Kathryn A.; Toney, Michael F.; Chabinyc, Michael L.; Yu, Lian; Ediger, M. D.

doi:10.1021/acs.chemmater.6b04877

Title: Highly organized smectic-like packing in vapor-deposited glasses of a liquid crystal

Journal Article · Mon Dec 26 00:00:00 EST 2016 · Chemistry of Materials

DOI:https://doi.org/10.1021/acs.chemmater.6b04877· OSTI ID:1360956

^[1]; Gomez, Jaritza ^[1]; Jiang, Jing ^[1];

^[1]; O’Hara, Kathryn A. ^[2]; Toney, Michael F. ^[3];

^[2]; Yu, Lian ^[1]; Ediger, M. D. ^[1]

Univ. of Wisconsin, Madison, WI (United States)
Univ. of California, Santa Barbara, CA (United States)
SLAC National Accelerator Lab., Menlo Park, CA (United States)

Glasses of a model smectic liquid crystal-forming molecule, itraconazole, were prepared by vapor deposition onto substrates with temperatures ranging from T_substrate = 0.78T_g to 1.02T_g, where T_g (=330 K) is the glass transition temperature. The films were characterized using X-ray scattering techniques. For T_substrate near and below T_g, glasses with layered smectic-like structures can be prepared and the layer spacing can be tuned by 16% through the choice of T_substrate. Remarkably, glasses prepared with T_substrate values above T_g exhibit levels of structural organization much higher than that of a thermally annealed film. These results are explained by a mechanism based upon a preferred molecular orientation and enhanced molecular motion at the free surface, indicating that molecular organization in the glass is independent of the anchoring preferred at the substrate. Furthermore, these results suggest new strategies for optimizing molecular packing within active layers of organic electronic and optoelectronic devices.

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Research Organization:: SLAC National Accelerator Lab. (SLAC), Menlo Park, CA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-76SF00515; DMR-1121288; DMR-1234320

OSTI ID:: 1360956

Journal Information:: Chemistry of Materials, Vol. 29, Issue 2; ISSN 0897-4756

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 26 works

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References (44)

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
Interplay of Molecular Orientation, Film Formation, and Optoelectronic Properties on Isoindigo- and Thienoisoindigo-Based Copolymers for Organic Field Effect Transistor and Organic Photovoltaic Applications Lu, Chien; Chen, Hsieh-Chih; Chuang, Wei-Ti Chemistry of Materials, Vol. 27, Issue 19 https://doi.org/10.1021/acs.chemmater.5b03197	journal	October 2015
Molecular orientation in small-molecule organic light-emitting diodes Yokoyama, Daisuke Journal of Materials Chemistry, Vol. 21, Issue 48 https://doi.org/10.1039/c1jm13417e	journal	January 2011
Exciton diffusion in organic photovoltaic cells Menke, S. Matthew; Holmes, Russell J. Energy Environ. Sci., Vol. 7, Issue 2 https://doi.org/10.1039/C3EE42444H	journal	January 2014
Liquid Crystals for Charge Transport, Luminescence, and Photonics O'Neill, M.; Kelly, S. M. Advanced Materials, Vol. 15, Issue 14 https://doi.org/10.1002/adma.200300009	journal	July 2003
Liquid Crystalline Ordering and Charge Transport in Semiconducting Materials Pisula, Wojciech; Zorn, Matthias; Chang, Ji Young Macromolecular Rapid Communications, Vol. 30, Issue 14 https://doi.org/10.1002/marc.200900251	journal	July 2009
Significant dependence of morphology and charge carrier mobility on substrate surface chemistry in high performance polythiophene semiconductor films Kline, R. Joseph; DeLongchamp, Dean M.; Fischer, Daniel A. Applied Physics Letters, Vol. 90, Issue 6 https://doi.org/10.1063/1.2472533	journal	February 2007
Liquid crystal alignment by rubbed polymer surfaces: a microscopic bond orientation model Stöhr, J.; Samant, M. G. Journal of Electron Spectroscopy and Related Phenomena, Vol. 98-99 https://doi.org/10.1016/S0368-2048(98)00286-2	journal	January 1999
Variable liquid crystal pretilt angles by nanostructured surfaces Yeung, Fion S.; Ho, Jacob Y.; Li, Y. W. Applied Physics Letters, Vol. 88, Issue 5 https://doi.org/10.1063/1.2171491	journal	January 2006
Thin film surface orientation for liquid crystals Janning, John L. Applied Physics Letters, Vol. 21, Issue 4 https://doi.org/10.1063/1.1654331	journal	August 1972
Surface Anchoring of Liquid Crystal Molecules on Various Substrates Castellano, Joseph A. Molecular Crystals and Liquid Crystals, Vol. 94, Issue 1-2 https://doi.org/10.1080/00268948308084245	journal	January 1983
Liquid Crystal Alignment on Carbonaceous Surfaces with Orientational Order Stohr, J. Science, Vol. 292, Issue 5525 https://doi.org/10.1126/science.1059866	journal	June 2001
Liquid-crystalline semiconducting polymers with high charge-carrier mobility McCulloch, Iain; Heeney, Martin; Bailey, Clare Nature Materials, Vol. 5, Issue 4 https://doi.org/10.1038/nmat1612	journal	March 2006
Large Area Liquid Crystal Monodomain Field-Effect Transistors van Breemen, Albert J. J. M.; Herwig, Peter T.; Chlon, Ceciel H. T. Journal of the American Chemical Society, Vol. 128, Issue 7 https://doi.org/10.1021/ja055337l	journal	February 2006
High Anisotropy of the Field-Effect Transistor Mobility in Magnetically Aligned Discotic Liquid-Crystalline Semiconductors Shklyarevskiy, Igor O.; Jonkheijm, Pascal; Stutzmann, Natalie Journal of the American Chemical Society, Vol. 127, Issue 46 https://doi.org/10.1021/ja054694t	journal	November 2005
Order Induced Charge Carrier Mobility Enhancement in Columnar Liquid Crystal Diodes Eccher, Juliana; Faria, Gregório C.; Bock, Harald ACS Applied Materials & Interfaces, Vol. 5, Issue 22 https://doi.org/10.1021/am403681q	journal	November 2013
Room Temperature Discotic Liquid Crystalline Thin Films of Hexa- p eri -hexabenzocoronene: Synthesis and Optoelectronic Properties Liu, Chong-yang; Fechtenkötter, Andreas; Watson, Mark D. Chemistry of Materials, Vol. 15, Issue 1 https://doi.org/10.1021/cm020701q	journal	January 2003
Tunable molecular orientation and elevated thermal stability of vapor-deposited organic semiconductors Dalal, Shakeel S.; Walters, Diane M.; Lyubimov, Ivan Proceedings of the National Academy of Sciences, Vol. 112, Issue 14 https://doi.org/10.1073/pnas.1421042112	journal	March 2015
High-Throughput Ellipsometric Characterization of Vapor-Deposited Indomethacin Glasses Dalal, Shakeel S.; Fakhraai, Zahra; Ediger, M. D. The Journal of Physical Chemistry B, Vol. 117, Issue 49 https://doi.org/10.1021/jp405005n	journal	August 2013
Charge accumulation at organic semiconductor interfaces due to a permanent dipole moment and its orientational order in bilayer devices Noguchi, Yutaka; Miyazaki, Yukimasa; Tanaka, Yuya Journal of Applied Physics, Vol. 111, Issue 11 https://doi.org/10.1063/1.4724349	journal	June 2012
Molecular packing in highly stable glasses of vapor-deposited tris-naphthylbenzene isomers Dawson, Kevin; Kopff, Laura A.; Zhu, Lei The Journal of Chemical Physics, Vol. 136, Issue 9 https://doi.org/10.1063/1.3686801	journal	March 2012
Structural Characterization of Vapor-Deposited Glasses of an Organic Hole Transport Material with X-ray Scattering Gujral, Ankit; O’Hara, Kathryn A.; Toney, Michael F. Chemistry of Materials, Vol. 27, Issue 9 https://doi.org/10.1021/acs.chemmater.5b00583	journal	April 2015
Orientation Control of Linear-Shaped Molecules in Vacuum-Deposited Organic Amorphous Films and Its Effect on Carrier Mobilities Yokoyama, Daisuke; Setoguchi, Yousuke; Sakaguchi, Akio Advanced Functional Materials, Vol. 20, Issue 3 https://doi.org/10.1002/adfm.200901684	journal	February 2010
Morphology of open films of discotic hexagonal columnar liquid crystals as probed by grazing incidence X-ray diffraction Grelet, Eric; Dardel, Sébastien; Bock, Harald The European Physical Journal E, Vol. 31, Issue 4 https://doi.org/10.1140/epje/i2010-10586-2	journal	April 2010
Infrared spectroscopic characterization of orientation and order of thin oligothiophene films Kramer, M.; Hoffmann, V. Optical Materials, Vol. 9, Issue 1-4 https://doi.org/10.1016/S0925-3467(97)00133-X	journal	January 1998
Thermal Evaporation versus Spin-Coating: Electrical Performance in Columnar Liquid Crystal OLEDs Eccher, Juliana; Zajaczkowski, Wojciech; Faria, Gregório C. ACS Applied Materials & Interfaces, Vol. 7, Issue 30 https://doi.org/10.1021/acsami.5b03496	journal	July 2015
Vapor deposition of a smectic liquid crystal: highly anisotropic, homogeneous glasses with tunable molecular orientation Gómez, Jaritza; Jiang, Jing; Gujral, Ankit Soft Matter, Vol. 12, Issue 11 https://doi.org/10.1039/C5SM02944A	journal	January 2016
Surface Self-Diffusion of Organic Glasses Brian, Caleb W.; Yu, Lian The Journal of Physical Chemistry A, Vol. 117, Issue 50 https://doi.org/10.1021/jp404944s	journal	August 2013
Surface Self-Diffusion of an Organic Glass Zhu, L.; Brian, C. W.; Swallen, S. F. Physical Review Letters, Vol. 106, Issue 25 https://doi.org/10.1103/PhysRevLett.106.256103	journal	June 2011
Impact of Absolute Stereochemistry on the Antiangiogenic and Antifungal Activities of Itraconazole Shi, Wei; Nacev, Benjamin A.; Bhat, Shridhar ACS Medicinal Chemistry Letters, Vol. 1, Issue 4 https://doi.org/10.1021/ml1000068	journal	April 2010
Analytical and semipreparative chiral separation ofcis-itraconazole on cellulose stationary phases by high-performance liquid chromatography Kurka, Ondřej; Kučera, Lukáš; Bednář, Petr Journal of Separation Science, Vol. 39, Issue 14 https://doi.org/10.1002/jssc.201600240	journal	June 2016
cis-2-sec-Butyl-4-{4-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-1-piperazinyl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (Itraconazole) Peeters, O. M.; Blaton, N. M.; De Ranter, C. J. Acta Crystallographica Section C Crystal Structure Communications, Vol. 52, Issue 9 https://doi.org/10.1107/S0108270196004180	journal	September 1996
Molecular dynamics of itraconazole at ambient and high pressure Tarnacka, M.; Adrjanowicz, K.; Kaminska, E. Physical Chemistry Chemical Physics, Vol. 15, Issue 47 https://doi.org/10.1039/c3cp52643g	journal	January 2013
Quantification of Thin Film Crystallographic Orientation Using X-ray Diffraction with an Area Detector Baker, Jessy L.; Jimison, Leslie H.; Mannsfeld, Stefan Langmuir, Vol. 26, Issue 11 https://doi.org/10.1021/la904840q	journal	June 2010
X-Ray Scattering from Semiconductors Fewster, Paul F. https://doi.org/10.1142/p137	book	January 2000
Current Topics in Smectic Liquid Crystal Research Lagerwall, Jan P. F.; Giesselmann, Frank ChemPhysChem, Vol. 7, Issue 1 https://doi.org/10.1002/cphc.200500472	journal	January 2006
A SAXS-WAXS study of the endothermic transitions in amorphous or supercooled liquid itraconazole Benmore, C. J.; Mou, Q.; Benmore, K. J. Thermochimica Acta, Vol. 644 https://doi.org/10.1016/j.tca.2016.10.004	journal	November 2016
Mechanical and Thermophysical Properties of Polymer Liquid Crystals Brostow, Witold Polymer Liquid Crystals Series https://doi.org/10.1007/978-1-4615-5799-9	book	January 1998
Observation of an anchoring transition in a discotic liquid crystal Perova, T. S.; Vij, J. K.; Kocot, A. Europhysics Letters (EPL), Vol. 44, Issue 2 https://doi.org/10.1209/epl/i1998-00445-5	journal	October 1998
Highly Stable Vapor-Deposited Glasses of Four Tris-naphthylbenzene Isomers Dawson, Kevin; Zhu, Lei; Kopff, Laura A. The Journal of Physical Chemistry Letters, Vol. 2, Issue 21 https://doi.org/10.1021/jz201174m	journal	October 2011
Smectic layering at the free surface of liquid crystals in the nematic phase: X-ray reflectivity Pershan, P. S.; Braslau, A.; Weiss, A. H. Physical Review A, Vol. 35, Issue 11 https://doi.org/10.1103/PhysRevA.35.4800	journal	June 1987
Surface effects and anchoring in liquid crystals Jerome, B. Reports on Progress in Physics, Vol. 54, Issue 3 https://doi.org/10.1088/0034-4885/54/3/002	journal	March 1991
Relaxation in glassforming liquids and amorphous solids Angell, C. A.; Ngai, K. L.; McKenna, G. B. Journal of Applied Physics, Vol. 88, Issue 6 https://doi.org/10.1063/1.1286035	journal	September 2000
Spontaneous electric fields in films of cis-methyl formate Plekan, Oksana; Cassidy, Andrew; Balog, Richard Physical Chemistry Chemical Physics, Vol. 14, Issue 28 https://doi.org/10.1039/c2cp41229b	journal	January 2012

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