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Title: Influence of Hydrogen Bonding on the Kinetic Stability of Vapor Deposited Glasses of Triazine Derivatives

Abstract

It has recently been established that physical vapor deposition (PVD) can produce organic glasses with enhanced kinetic stability, high density, and anisotropic packing, with the substrate temperature during deposition (Tsubstrate) as the key control parameter. The influence of hydrogen bonding on the formation of PVD glasses has not been fully explored. Herein, we use a high-throughput preparation method to vapor-deposit three triazine derivatives over a wide range of Tsubstrate, from 0.69 to 1.08Tg, where Tg is the glass transition temperature. These model systems are structural analogues containing a functional group with different H-bonding capability at the 2-position of a triazine ring: (1) 2-methylamino-4,6-bis(3,5-dimethyl-phenylamino)-1,3,5-triazine (NHMe) (H-bond donor), (2) 2-methoxy-4,6-bis(3,5-dimethyl-phenylamino)-1,3,5-triazine (OMe) (H-bond acceptor), and (3) 2-ethyl-4,6-bis(3,5-dimethyl-phenylamino)-1,3,5-triazine (Et) (none). Using spectroscopic ellipsometry, we find that the Et and OMe compounds form PVD glasses with relatively high kinetic stability, with the transformation time (scaled by the α-relaxation time) on the order of 103, comparable to other highly stable glasses formed by PVD. In contrast, PVD glasses of NHMe are only slightly more stable than the corresponding liquid-cooled glass. Using IR spectroscopy, we find that both the supercooled liquid and the PVD glasses of the NHMe derivative show a higher average number of bonded NHmore » per molecule than that in the other two compounds. These results suggest that H-bonds hinder the formation of stable glasses, perhaps by limiting the surface mobility. Interestingly, despite this difference in kinetic stability, all three compounds show properties typically observed in highly stable glasses prepared by PVD, including a higher density and anisotropic molecular packing (as characterized by IR and wide-angle X-ray scattering).« less

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [3]; ORCiD logo [2]; ORCiD logo [1]
  1. Departement de chimie, Universite de Montreal, C.P. 6128, Succ. Centre-Ville, Montreal, Quebec H3C 3J7, Canada
  2. Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States
  3. Department of Chemistry and Chemical Engineering, Royal Military College of Canada, Kingston, Ontario K7K 7B4
Publication Date:
Research Org.:
University of Wisconsin-Madison
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1352153
DOE Contract Number:  
SC0002161
Resource Type:
Data
Data Type:
Figures/Plots
Country of Publication:
United States
Availability:
University of Wisconsin-Madison
Language:
English
Subject:
36 MATERIALS SCIENCE; Stable glasses, Hydrogen bonding, Infrared spectroscopy, wide angle x-ray scattering, Spectroscopic Ellipsometry

Citation Formats

Laventure, Audrey, Gujral, Ankit, Lebel, Olivier, Ediger, Mark, and Pellerin, Christian. Influence of Hydrogen Bonding on the Kinetic Stability of Vapor Deposited Glasses of Triazine Derivatives. United States: N. p., 2017. Web. doi:10.11578/1352153.
Laventure, Audrey, Gujral, Ankit, Lebel, Olivier, Ediger, Mark, & Pellerin, Christian. Influence of Hydrogen Bonding on the Kinetic Stability of Vapor Deposited Glasses of Triazine Derivatives. United States. doi:10.11578/1352153.
Laventure, Audrey, Gujral, Ankit, Lebel, Olivier, Ediger, Mark, and Pellerin, Christian. Wed . "Influence of Hydrogen Bonding on the Kinetic Stability of Vapor Deposited Glasses of Triazine Derivatives". United States. doi:10.11578/1352153. https://www.osti.gov/servlets/purl/1352153.
@article{osti_1352153,
title = {Influence of Hydrogen Bonding on the Kinetic Stability of Vapor Deposited Glasses of Triazine Derivatives},
author = {Laventure, Audrey and Gujral, Ankit and Lebel, Olivier and Ediger, Mark and Pellerin, Christian},
abstractNote = {It has recently been established that physical vapor deposition (PVD) can produce organic glasses with enhanced kinetic stability, high density, and anisotropic packing, with the substrate temperature during deposition (Tsubstrate) as the key control parameter. The influence of hydrogen bonding on the formation of PVD glasses has not been fully explored. Herein, we use a high-throughput preparation method to vapor-deposit three triazine derivatives over a wide range of Tsubstrate, from 0.69 to 1.08Tg, where Tg is the glass transition temperature. These model systems are structural analogues containing a functional group with different H-bonding capability at the 2-position of a triazine ring: (1) 2-methylamino-4,6-bis(3,5-dimethyl-phenylamino)-1,3,5-triazine (NHMe) (H-bond donor), (2) 2-methoxy-4,6-bis(3,5-dimethyl-phenylamino)-1,3,5-triazine (OMe) (H-bond acceptor), and (3) 2-ethyl-4,6-bis(3,5-dimethyl-phenylamino)-1,3,5-triazine (Et) (none). Using spectroscopic ellipsometry, we find that the Et and OMe compounds form PVD glasses with relatively high kinetic stability, with the transformation time (scaled by the α-relaxation time) on the order of 103, comparable to other highly stable glasses formed by PVD. In contrast, PVD glasses of NHMe are only slightly more stable than the corresponding liquid-cooled glass. Using IR spectroscopy, we find that both the supercooled liquid and the PVD glasses of the NHMe derivative show a higher average number of bonded NH per molecule than that in the other two compounds. These results suggest that H-bonds hinder the formation of stable glasses, perhaps by limiting the surface mobility. Interestingly, despite this difference in kinetic stability, all three compounds show properties typically observed in highly stable glasses prepared by PVD, including a higher density and anisotropic molecular packing (as characterized by IR and wide-angle X-ray scattering).},
doi = {10.11578/1352153},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Wed Feb 01 00:00:00 EST 2017},
month = {Wed Feb 01 00:00:00 EST 2017}
}

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