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Title: Vapor deposition of a nonmesogen prepares highly structured organic glasses

Abstract

Significance Organic glasses are useful, versatile materials for current and future organic electronic technologies. They are nonequilibrium materials, so a single-component system can be processed in different ways to create a wide range of solids with diverse structural and optical properties. In this work, we use physical vapor deposition to prepare glasses with structure similar to that of an aligned smectic liquid crystal from a molecule that does not have any liquid crystal phases. This shows the potential to create highly structured glasses from a wide range of molecules.

Authors:
ORCiD logo [1];  [2];  [2]; ORCiD logo [3];  [4];  [2];  [1]
  1. Department of Chemistry, University of Wisconsin–Madison, Madison, WI 53706,
  2. The National Institute of Standards and Technology, Gaithersburg, MD 20899,
  3. Stanford Synchrotron Radiation Lightsource, SLAC National Accelerator Laboratory, Menlo Park, CA 94025,
  4. Department of Chemistry, University of Wisconsin–Madison, Madison, WI 53706,, School of Pharmacy, University of Wisconsin–Madison, Madison, WI 53705
Publication Date:
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1566219
Grant/Contract Number:  
AC02-76SF00515
Resource Type:
Published Article
Journal Name:
Proceedings of the National Academy of Sciences of the United States of America
Additional Journal Information:
Journal Name: Proceedings of the National Academy of Sciences of the United States of America Journal Volume: 116 Journal Issue: 43; Journal ID: ISSN 0027-8424
Publisher:
Proceedings of the National Academy of Sciences
Country of Publication:
United States
Language:
English

Citation Formats

Bishop, Camille, Thelen, Jacob L., Gann, Eliot, Toney, Michael F., Yu, Lian, DeLongchamp, Dean M., and Ediger, M. D. Vapor deposition of a nonmesogen prepares highly structured organic glasses. United States: N. p., 2019. Web. doi:10.1073/pnas.1908445116.
Bishop, Camille, Thelen, Jacob L., Gann, Eliot, Toney, Michael F., Yu, Lian, DeLongchamp, Dean M., & Ediger, M. D. Vapor deposition of a nonmesogen prepares highly structured organic glasses. United States. https://doi.org/10.1073/pnas.1908445116
Bishop, Camille, Thelen, Jacob L., Gann, Eliot, Toney, Michael F., Yu, Lian, DeLongchamp, Dean M., and Ediger, M. D. Mon . "Vapor deposition of a nonmesogen prepares highly structured organic glasses". United States. https://doi.org/10.1073/pnas.1908445116.
@article{osti_1566219,
title = {Vapor deposition of a nonmesogen prepares highly structured organic glasses},
author = {Bishop, Camille and Thelen, Jacob L. and Gann, Eliot and Toney, Michael F. and Yu, Lian and DeLongchamp, Dean M. and Ediger, M. D.},
abstractNote = {Significance Organic glasses are useful, versatile materials for current and future organic electronic technologies. They are nonequilibrium materials, so a single-component system can be processed in different ways to create a wide range of solids with diverse structural and optical properties. In this work, we use physical vapor deposition to prepare glasses with structure similar to that of an aligned smectic liquid crystal from a molecule that does not have any liquid crystal phases. This shows the potential to create highly structured glasses from a wide range of molecules.},
doi = {10.1073/pnas.1908445116},
journal = {Proceedings of the National Academy of Sciences of the United States of America},
number = 43,
volume = 116,
place = {United States},
year = {2019},
month = {9}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1073/pnas.1908445116

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Cited by: 8 works
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Works referenced in this record:

Structural Characterization of Vapor-Deposited Glasses of an Organic Hole Transport Material with X-ray Scattering
journal, April 2015


Dynamic Control of Light Direction Enabled by Stimuli-Responsive Liquid Crystal Gratings
journal, December 2018

  • Zola, Rafael S.; Bisoyi, Hari Krishna; Wang, Hao
  • Advanced Materials, Vol. 31, Issue 7
  • DOI: 10.1002/adma.201806172

Mechanical Properties of Structure-Tunable, Vapor-Deposited TPD Glass
journal, November 2018

  • Tangpatjaroen, Chaiyapat; Bagchi, Kushal; Martínez, Rafael A.
  • The Journal of Physical Chemistry C, Vol. 122, Issue 48
  • DOI: 10.1021/acs.jpcc.8b09718

A detailed assignment of NEXAFS resonances of imidazolium based ionic liquids
journal, January 2016

  • Ehlert, Christopher; Holzweber, Markus; Lippitz, Andreas
  • Physical Chemistry Chemical Physics, Vol. 18, Issue 12
  • DOI: 10.1039/C5CP07434G

Printable and flexible electronics: from TFTs to bioelectronic devices
journal, January 2015

  • Magliulo, M.; Mulla, M. Y.; Singh, M.
  • Journal of Materials Chemistry C, Vol. 3, Issue 48
  • DOI: 10.1039/C5TC02737C

Glassy Liquid Crystal of the Nematic Phase of N -( o -Hydroxy- p -methoxybenzylidene)- p -butylaniline
journal, October 1971

  • Sorai, Michio; Seki, Syûzô
  • Bulletin of the Chemical Society of Japan, Vol. 44, Issue 10
  • DOI: 10.1246/bcsj.44.2887

Using deposition rate to increase the thermal and kinetic stability of vapor-deposited hole transport layer glasses via a simple sublimation apparatus
journal, May 2017

  • Kearns, Kenneth L.; Krzyskowski, Paige; Devereaux, Zachary
  • The Journal of Chemical Physics, Vol. 146, Issue 20
  • DOI: 10.1063/1.4979814

Inner shell excitation and ionization of the monohalobenzenes
journal, January 1978

  • Hitchcock, A. P.; Pocock, M.; Brion, C. E.
  • Journal of Electron Spectroscopy and Related Phenomena, Vol. 13, Issue 3
  • DOI: 10.1016/0368-2048(78)85040-3

Effects of microstructure formation on the stability of vapor-deposited glasses
journal, March 2019

  • Moore, Alex R.; Huang, Georgia; Wolf, Sarah
  • Proceedings of the National Academy of Sciences, Vol. 116, Issue 13
  • DOI: 10.1073/pnas.1821761116

NEXAFS and ARUP Spectroscopy of an Organic Single Crystal: α-Perylene
journal, February 2000

  • Zimmermann, U.; Schnitzler, G.; Wüstenhagen, V.
  • Molecular Crystals and Liquid Crystals Science and Technology. Section A. Molecular Crystals and Liquid Crystals, Vol. 339, Issue 1
  • DOI: 10.1080/10587250008031046

High Carrier Mobility up to 0.1 cm2 V-1 s-1 at Ambient Temperatures in Thiophene-Based Smectic Liquid Crystals
journal, March 2005


Precise Structure of Pentacene Monolayers on Amorphous Silicon Oxide and Relation to Charge Transport
journal, June 2009

  • Mannsfeld, Stefan C. B.; Virkar, Ajay; Reese, Colin
  • Advanced Materials, Vol. 21, Issue 22
  • DOI: 10.1002/adma.200803328

Highly Organized Smectic-like Packing in Vapor-Deposited Glasses of a Liquid Crystal
journal, January 2017


Organic Glasses with Exceptional Thermodynamic and Kinetic Stability
journal, January 2007


Flow-induced elastic anisotropy of metallic glasses
journal, June 2016


High-performance organic light-emitting diodes comprising ultrastable glass layers
journal, May 2018

  • Ràfols-Ribé, Joan; Will, Paul-Anton; Hänisch, Christian
  • Science Advances, Vol. 4, Issue 5
  • DOI: 10.1126/sciadv.aar8332

The yield and thermoelastic properties of oriented poly(methyl methacrylate)
journal, February 1987


All-atom simulation of molecular orientation in vapor-deposited organic light-emitting diodes
journal, January 2018

  • Youn, Yong; Yoo, Dongsun; Song, Hochul
  • Journal of Materials Chemistry C, Vol. 6, Issue 5
  • DOI: 10.1039/C7TC05278B

Tunable molecular orientation and elevated thermal stability of vapor-deposited organic semiconductors
journal, March 2015

  • Dalal, Shakeel S.; Walters, Diane M.; Lyubimov, Ivan
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 14
  • DOI: 10.1073/pnas.1421042112

A SAXS-WAXS study of the endothermic transitions in amorphous or supercooled liquid itraconazole
journal, November 2016


Vapor-Deposited Glasses with Long-Range Columnar Liquid Crystalline Order
journal, October 2017


Smectic layering at the free surface of liquid crystals in the nematic phase: X-ray reflectivity
journal, June 1987


Organic Glasses with Tunable Liquid-Crystalline Order
journal, February 2018


Molecular Dynamics of the Supercooled Pharmaceutical Agent Posaconazole Studied via Differential Scanning Calorimetry and Dielectric and Mechanical Spectroscopies
journal, September 2013

  • Adrjanowicz, K.; Kaminski, K.; Wlodarczyk, P.
  • Molecular Pharmaceutics, Vol. 10, Issue 10
  • DOI: 10.1021/mp4003915

Quantitative Determination of Organic Semiconductor Microstructure from the Molecular to Device Scale
journal, June 2012

  • Rivnay, Jonathan; Mannsfeld, Stefan C. B.; Miller, Chad E.
  • Chemical Reviews, Vol. 112, Issue 10
  • DOI: 10.1021/cr3001109

Nika : software for two-dimensional data reduction
journal, March 2012


Trends in the Carbonyl Core (C 1S, O 1S) → π* C=O Transition in the Near-Edge X-ray Absorption Fine Structure Spectra of Organic Molecules
journal, August 2002

  • Urquhart, S. G.; Ade, H.
  • The Journal of Physical Chemistry B, Vol. 106, Issue 34
  • DOI: 10.1021/jp0255379

Nematic-like stable glasses without equilibrium liquid crystal phases
journal, February 2017

  • Gómez, Jaritza; Gujral, Ankit; Huang, Chengbin
  • The Journal of Chemical Physics, Vol. 146, Issue 5
  • DOI: 10.1063/1.4974829

New Finding of Glassy Liquid Crystal – a Non-equilibrium State of Cholesteryl Hydrogen Phthalate
journal, May 1971

  • Tsuji, Kazuhiro; Sorai, Michio; Seki, Syûzô
  • Bulletin of the Chemical Society of Japan, Vol. 44, Issue 5
  • DOI: 10.1246/bcsj.44.1452

Energy-Cascade Organic Photovoltaic Devices Incorporating a Host–Guest Architecture
journal, January 2015

  • Menke, S. Matthew; Holmes, Russell J.
  • ACS Applied Materials & Interfaces, Vol. 7, Issue 4
  • DOI: 10.1021/am508332n

Mixing Behavior in Small Molecule:Fullerene Organic Photovoltaics
journal, March 2017


Vapor deposition of a smectic liquid crystal: highly anisotropic, homogeneous glasses with tunable molecular orientation
journal, January 2016

  • Gómez, Jaritza; Jiang, Jing; Gujral, Ankit
  • Soft Matter, Vol. 12, Issue 11
  • DOI: 10.1039/C5SM02944A

Surface Layering in Liquid Gallium: An X-Ray Reflectivity Study
journal, September 1995


Chemical Trends in the Near-Edge X-ray Absorption Fine Structure of Monosubstituted and Para-Bisubstituted Benzenes
journal, November 2004

  • Cooney, Ryan R.; Urquhart, Stephen G.
  • The Journal of Physical Chemistry B, Vol. 108, Issue 47
  • DOI: 10.1021/jp046868j

Transformation kinetics of vapor-deposited thin film organic glasses: the role of stability and molecular packing anisotropy
journal, January 2015

  • Rodríguez-Tinoco, Cristian; Gonzalez-Silveira, Marta; Ràfols-Ribé, Joan
  • Physical Chemistry Chemical Physics, Vol. 17, Issue 46
  • DOI: 10.1039/C5CP04692K

Quick AS NEXAFS Tool ( QANT ): a program for NEXAFS loading and analysis developed at the Australian Synchrotron
journal, January 2016

  • Gann, Eliot; McNeill, Christopher R.; Tadich, Anton
  • Journal of Synchrotron Radiation, Vol. 23, Issue 1
  • DOI: 10.1107/S1600577515018688

Dynamics of glass-forming liquids. XVI. Observation of ultrastable glass transformation via dielectric spectroscopy
journal, March 2013

  • Chen, Z.; Sepúlveda, A.; Ediger, M. D.
  • The Journal of Chemical Physics, Vol. 138, Issue 12
  • DOI: 10.1063/1.4771695

Thermal Evaporation versus Spin-Coating: Electrical Performance in Columnar Liquid Crystal OLEDs
journal, July 2015

  • Eccher, Juliana; Zajaczkowski, Wojciech; Faria, Gregório C.
  • ACS Applied Materials & Interfaces, Vol. 7, Issue 30
  • DOI: 10.1021/acsami.5b03496

Surface mobility of molecular glasses and its importance in physical stability
journal, May 2016


Glassy Carbon as an Absolute Intensity Calibration Standard for Small-Angle Scattering
journal, August 2009

  • Zhang, Fan; Ilavsky, Jan; Long, Gabrielle G.
  • Metallurgical and Materials Transactions A, Vol. 41, Issue 5
  • DOI: 10.1007/s11661-009-9950-x

Molecular Structure of Canonical Liquid Crystal Interfaces
journal, March 2017

  • Sadati, Monirosadat; Ramezani-Dakhel, Hadi; Bu, Wei
  • Journal of the American Chemical Society, Vol. 139, Issue 10
  • DOI: 10.1021/jacs.7b00167

Hiking down the Energy Landscape:  Progress Toward the Kauzmann Temperature via Vapor Deposition
journal, April 2008

  • Kearns, Kenneth L.; Swallen, Stephen F.; Ediger, M. D.
  • The Journal of Physical Chemistry B, Vol. 112, Issue 16
  • DOI: 10.1021/jp7113384

Surface effects and anchoring in liquid crystals
journal, March 1991


Distribution functions in three liquid crystals from X-ray diffraction measurements
journal, September 1979


Horizontal orientation of linear-shaped organic molecules having bulky substituents in neat and doped vacuum-deposited amorphous films
journal, February 2009


Origin of Anisotropic Molecular Packing in Vapor-Deposited Alq3 Glasses
journal, December 2018

  • Bagchi, Kushal; Jackson, Nicholas E.; Gujral, Ankit
  • The Journal of Physical Chemistry Letters, Vol. 10, Issue 2
  • DOI: 10.1021/acs.jpclett.8b03582

Surface‐induced ordering: A model for vapor‐deposition growth of amorphous materials
journal, April 1994


Birefringent Stable Glass with Predominantly Isotropic Molecular Orientation
journal, August 2017


Substrate temperature controls molecular orientation in two-component vapor-deposited glasses
journal, January 2016

  • Jiang, J.; Walters, D. M.; Zhou, D.
  • Soft Matter, Vol. 12, Issue 13, p. 3265-3270
  • DOI: 10.1039/C6SM00262E

Thermodynamic investigation on glassy states of pure simple compounds
journal, November 1974


Influence of Molecular Shape on the Thermal Stability and Molecular Orientation of Vapor-Deposited Organic Semiconductors
journal, July 2017

  • Walters, Diane M.; Antony, Lucas; de Pablo, Juan J.
  • The Journal of Physical Chemistry Letters, Vol. 8, Issue 14, p. 3380-3386
  • DOI: 10.1021/acs.jpclett.7b01097

Molecular orientation in small-molecule organic light-emitting diodes
journal, January 2011

  • Yokoyama, Daisuke
  • Journal of Materials Chemistry, Vol. 21, Issue 48
  • DOI: 10.1039/c1jm13417e

Carrier Transport Properties of Monodisperse Glassy-Nematic Oligofluorenes in Organic Field-Effect Transistors
journal, January 2005

  • Yasuda, Takeshi; Fujita, Katsuhiko; Tsutsui, Tetsuo
  • Chemistry of Materials, Vol. 17, Issue 2
  • DOI: 10.1021/cm048532s

Mobility enhancement in conjugated polymer field-effect transistors through chain alignment in a liquid-crystalline phase
journal, July 2000

  • Sirringhaus, H.; Wilson, R. J.; Friend, R. H.
  • Applied Physics Letters, Vol. 77, Issue 3
  • DOI: 10.1063/1.126991

Order Induced Charge Carrier Mobility Enhancement in Columnar Liquid Crystal Diodes
journal, November 2013

  • Eccher, Juliana; Faria, Gregório C.; Bock, Harald
  • ACS Applied Materials & Interfaces, Vol. 5, Issue 22
  • DOI: 10.1021/am403681q

Orientational anisotropy in simulated vapor-deposited molecular glasses
journal, September 2015

  • Lyubimov, Ivan; Antony, Lucas; Walters, Diane M.
  • The Journal of Chemical Physics, Vol. 143, Issue 9
  • DOI: 10.1063/1.4928523