Tenfold increase in the photostability of an azobenzene guest in vapor-deposited glass mixtures

Qiu, Yue; Antony, Lucas W.; Torkelson, John M.; de Pablo, Juan J.; Ediger, M. D.

doi:10.1063/1.5052003

Title: Tenfold increase in the photostability of an azobenzene guest in vapor-deposited glass mixtures

Abstract

Improvements to the photostability of organic glasses for use in electronic applications have generally relied on the modification of the chemical structure. We show here that the photostability of a guest molecule can also be significantly improved—without chemical modification—by using physical vapor deposition to pack molecules more densely. Photoisomerization of the substituted azobenzene, 4,4'-diphenyl azobenzene, was studied in a vapor-deposited glass matrix of celecoxib. We directly measure photoisomerization of trans- to cis-states via Ultraviolet-visible (UV-Vis) spectroscopy and show that the rate of photoisomerization depends upon the substrate temperature used during co-deposition of the glass. Photostability correlates reasonably with the density of the glass, where the optimum glass is about tenfold more photostable than the liquid-cooled glass. Molecular simulations, which mimic photoisomerization, also demonstrate that photoreaction of a guest molecule can be suppressed in vapor-deposited glasses. Finally, from the simulations, we estimate that the region that is disrupted by a single photoisomerization event encompasses approximately 5 molecules.

Authors:

^[1];

^[2];

^[3]; de Pablo, Juan J. ^[2];

^[1]

Univ. of Wisconsin, Madison, WI (United States)
Univ. of Chicago, IL (United States)
Northwestern Univ., Evanston, IL (United States)

Publication Date:: Tue Nov 27 00:00:00 EST 2018

Research Org.:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES); US Army Research Office (ARO)

OSTI Identifier:: 1610656

Grant/Contract Number:: SC0002161; W911NF-15-1-0568

Resource Type:: Journal Article: Accepted Manuscript

Journal Name:: Journal of Chemical Physics

Additional Journal Information:: Journal Volume: 149; Journal Issue: 20; Journal ID: ISSN 0021-9606

Publisher:: American Institute of Physics (AIP)

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 71 CLASSICAL AND QUANTUM MECHANICS, GENERAL PHYSICS; chemistry; physics

Citation Formats


                    Qiu, Yue, Antony, Lucas W., Torkelson, John M., de Pablo, Juan J., and Ediger, M. D. Tenfold increase in the photostability of an azobenzene guest in vapor-deposited glass mixtures.  United States: N. p., 2018. 
        Web.  doi:10.1063/1.5052003.

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                    Qiu, Yue, Antony, Lucas W., Torkelson, John M., de Pablo, Juan J., & Ediger, M. D. Tenfold increase in the photostability of an azobenzene guest in vapor-deposited glass mixtures.  United States.  https://doi.org/10.1063/1.5052003

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                    Qiu, Yue, Antony, Lucas W., Torkelson, John M., de Pablo, Juan J., and Ediger, M. D. 2018.  
        "Tenfold increase in the photostability of an azobenzene guest in vapor-deposited glass mixtures".  United States.  https://doi.org/10.1063/1.5052003.  https://www.osti.gov/servlets/purl/1610656.

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@article{osti_1610656,

  title        = {Tenfold increase in the photostability of an azobenzene guest in vapor-deposited glass mixtures},

  author       = {Qiu, Yue and Antony, Lucas W. and Torkelson, John M. and de Pablo, Juan J. and Ediger, M. D.},

  abstractNote = {Improvements to the photostability of organic glasses for use in electronic applications have generally relied on the modification of the chemical structure. We show here that the photostability of a guest molecule can also be significantly improved—without chemical modification—by using physical vapor deposition to pack molecules more densely. Photoisomerization of the substituted azobenzene, 4,4'-diphenyl azobenzene, was studied in a vapor-deposited glass matrix of celecoxib. We directly measure photoisomerization of trans- to cis-states via Ultraviolet-visible (UV-Vis) spectroscopy and show that the rate of photoisomerization depends upon the substrate temperature used during co-deposition of the glass. Photostability correlates reasonably with the density of the glass, where the optimum glass is about tenfold more photostable than the liquid-cooled glass. Molecular simulations, which mimic photoisomerization, also demonstrate that photoreaction of a guest molecule can be suppressed in vapor-deposited glasses. Finally, from the simulations, we estimate that the region that is disrupted by a single photoisomerization event encompasses approximately 5 molecules.},

  doi          = {10.1063/1.5052003},

  url          = {https://www.osti.gov/biblio/1610656},
  journal      = {Journal of Chemical Physics},

  issn         = {0021-9606},

  number       = 20,

  volume       = 149,

  place        = {United States},

  year         = {Tue Nov 27 00:00:00 EST 2018},

  month        = {Tue Nov 27 00:00:00 EST 2018}

}

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Title: Tenfold increase in the photostability of an azobenzene guest in vapor-deposited glass mixtures

Abstract

Citation Formats

50th Anniversary Perspective : Challenges in the Dynamics and Kinetics of Glass-Forming Polymers journal, August 2017

High-Modulus Organic Glasses Prepared by Physical Vapor Deposition journal, January 2010

Photochromic and fluorescent probe studies in glassy polymer matrices. 5. Effects of physical aging on bisphenol A polycarbonate and poly(vinyl acetate) as sensed by a size distribution of photochromic probes journal, August 1992

X-ray Diffraction Analysis of Nonequilibrium States in Crystals: Observation of an Unstable Conformer in Flash-Cooled Crystals journal, March 2004

Glass transition in vapor deposited thin films of toluene journal, August 2009

Enhanced Electrical Properties and Air Stability of Amorphous Organic Thin Films by Engineering Film Density journal, November 2017

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

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Tenfold increase in the lifetime of blue phosphorescent organic light-emitting diodes journal, September 2014

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Characteristics and Significance of the Amorphous State in Pharmaceutical Systems journal, January 1997

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Colloquium : The glass transition and elastic models of glass-forming liquids journal, September 2006

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Highly Efficient TADF OLEDs: How the Emitter-Host Interaction Controls Both the Excited State Species and Electrical Properties of the Devices to Achieve Near 100% Triplet Harvesting and High Efficiency journal, August 2014

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The effect of chemical structure on the stability of physical vapor deposited glasses of 1,3,5-triarylbenzene journal, August 2015

Highly stable glasses of celecoxib: Influence on thermo-kinetic properties, microstructure and response towards crystal growth journal, January 2015

Photostability Can Be Significantly Modulated by Molecular Packing in Glasses journal, August 2016

Character of Devitrification, Viewed from Enthalpic Paths, of the Vapor-Deposited Ethylbenzene Glasses journal, December 2011

Organic host materials for phosphorescent organic light-emitting diodes journal, January 2011

Surface diffusion and surface crystal growth of tris -naphthyl benzene glasses journal, August 2016

50th Anniversary Perspective : Challenges in the Dynamics and Kinetics of Glass-Forming Polymers
journal, August 2017

High-Modulus Organic Glasses Prepared by Physical Vapor Deposition
journal, January 2010

Photochromic and fluorescent probe studies in glassy polymer matrices. 5. Effects of physical aging on bisphenol A polycarbonate and poly(vinyl acetate) as sensed by a size distribution of photochromic probes
journal, August 1992

X-ray Diffraction Analysis of Nonequilibrium States in Crystals: Observation of an Unstable Conformer in Flash-Cooled Crystals
journal, March 2004

Glass transition in vapor deposited thin films of toluene
journal, August 2009

Enhanced Electrical Properties and Air Stability of Amorphous Organic Thin Films by Engineering Film Density
journal, November 2017

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

Organic Light-Emitting Diodes with 30% External Quantum Efficiency Based on a Horizontally Oriented Emitter
journal, March 2013

Vapor-deposited non-crystalline phase vs ordinary glasses and supercooled liquids: Subtle thermodynamic and kinetic differences
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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

Stability of thin film glasses of toluene and ethylbenzene formed by vapor deposition: an in situ nanocalorimetric study
journal, January 2010

Perspective: Highly stable vapor-deposited glasses
journal, December 2017

Tenfold increase in the lifetime of blue phosphorescent organic light-emitting diodes
journal, September 2014

Photostability of laser dyes incorporated in formamide SiO2 ORMOSILs
journal, July 2006

Polymeric solid-state dye lasers
journal, February 1995

A nonconjugated radical polymer glass with high electrical conductivity
journal, March 2018

Vapor-deposited organic glasses exhibit enhanced stability against photodegradation
journal, January 2018

Characteristics and Significance of the Amorphous State in Pharmaceutical Systems
journal, January 1997

Root Causes of the Limited Electroluminescence Stability of Organic Light-Emitting Devices Made by Solution-Coating
journal, May 2018

Colloquium : The glass transition and elastic models of glass-forming liquids
journal, September 2006

Stability of organic solar cells: challenges and strategies
journal, January 2016

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journal, January 2007

Glasses of three alkyl phosphates show a range of kinetic stabilities when prepared by physical vapor deposition
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Communication: Surface-facilitated softening of ordinary and vapor-deposited glasses
journal, August 2017

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journal, June 2011

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journal, May 2018

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

Photochromic and fluorescent probe studies in glassy polymer matrices. 4. Effects of physical aging on poly(methyl methacrylate) as sensed by a size distribution of photochromic probes
journal, March 1992

Highly Efficient TADF OLEDs: How the Emitter-Host Interaction Controls Both the Excited State Species and Electrical Properties of the Devices to Achieve Near 100% Triplet Harvesting and High Efficiency
journal, August 2014

Photodegradation of the organic/metal cathode interface in organic light-emitting devices
journal, August 2010

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

Anomalously high-density glass of ethylbenzene prepared by vapor deposition at temperatures close to the glass-transition temperature
journal, June 2008

High-Throughput Ellipsometric Characterization of Vapor-Deposited Indomethacin Glasses
journal, August 2013

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

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

The effect of chemical structure on the stability of physical vapor deposited glasses of 1,3,5-triarylbenzene
journal, August 2015

Highly stable glasses of celecoxib: Influence on thermo-kinetic properties, microstructure and response towards crystal growth
journal, January 2015

Photostability Can Be Significantly Modulated by Molecular Packing in Glasses
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Character of Devitrification, Viewed from Enthalpic Paths, of the Vapor-Deposited Ethylbenzene Glasses
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Organic host materials for phosphorescent organic light-emitting diodes
journal, January 2011

Surface diffusion and surface crystal growth of tris -naphthyl benzene glasses
journal, August 2016