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Title: Triazolium based ionic liquid crystals: Effect of asymmetric substitution

Abstract

A new series of ten different asymmetrical 1-dodecyl-3-alkyl-triazolium bromides, [C 12C nTr][Br], has been synthesized and their mesomorphic behavior studied by DSC (differential scanning calorimetry), POM (polarizing optical microscopy) and SAXS (small angle X-ray scattering). The influence of the chain length of the triazolium salts is investigated to explore the effect of asymmetric substitution on the phase behaviour of these compounds. For that reason, the length of one alkyl chain was varied from 14 to 1 carbon atoms (n = 14, 12, 10, 8–4, 2, 1) while the other alkyl chain was kept at 12 carbon. Single crystal X-ray structure analysis of compounds [C 12C 12Tr][Br] and [C 12C 5Tr][Br] reveal that the cations adopt a U-shaped conformation with head-to-head arranged triazolium cores. In contrast, for [C 12C 1Tr][Br], a rod like shape of the cation with interdigitated alkyl chains is found. All investigated compounds are thermotropic liquid crystals. Higher ordered smectic phases, smectic C as well as smectic A phases were found depending on the chain length of the cation. Moreover, the clearing point temperature decreases with decreasing chain length with exception for the n-dodecyl-3-alkyltrizoliumbromides with the two shortest alkyl chains, [C 12C 2Tr][Br] and [C 12C 1Tr][Br], whichmore » present higher clearing temperatures (86 and 156 °C) and are structurally distinctly different.« less

Authors:
 [1];  [2]
  1. Ruhr-Univ. Bochum, Bochum (Germany)
  2. Ruhr-Univ. Bochum, Bochum (Germany); Ames Lab., Ames, IA (United States)
Publication Date:
Research Org.:
Ames Laboratory (AMES), Ames, IA (United States)
Sponsoring Org.:
USDOE Advanced Research Projects Agency - Energy (ARPA-E)
OSTI Identifier:
1239144
Report Number(s):
IS-J-8632
Journal ID: ISSN 2046-2069; RSCACL
Grant/Contract Number:  
AC02-07CH11358
Resource Type:
Accepted Manuscript
Journal Name:
RSC Advances
Additional Journal Information:
Journal Volume: 5; Journal Issue: 22; Journal ID: ISSN 2046-2069
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Stappert, K., and Mudring, A. -V. Triazolium based ionic liquid crystals: Effect of asymmetric substitution. United States: N. p., 2015. Web. doi:10.1039/c4ra14961k.
Stappert, K., & Mudring, A. -V. Triazolium based ionic liquid crystals: Effect of asymmetric substitution. United States. doi:10.1039/c4ra14961k.
Stappert, K., and Mudring, A. -V. Tue . "Triazolium based ionic liquid crystals: Effect of asymmetric substitution". United States. doi:10.1039/c4ra14961k. https://www.osti.gov/servlets/purl/1239144.
@article{osti_1239144,
title = {Triazolium based ionic liquid crystals: Effect of asymmetric substitution},
author = {Stappert, K. and Mudring, A. -V.},
abstractNote = {A new series of ten different asymmetrical 1-dodecyl-3-alkyl-triazolium bromides, [C12CnTr][Br], has been synthesized and their mesomorphic behavior studied by DSC (differential scanning calorimetry), POM (polarizing optical microscopy) and SAXS (small angle X-ray scattering). The influence of the chain length of the triazolium salts is investigated to explore the effect of asymmetric substitution on the phase behaviour of these compounds. For that reason, the length of one alkyl chain was varied from 14 to 1 carbon atoms (n = 14, 12, 10, 8–4, 2, 1) while the other alkyl chain was kept at 12 carbon. Single crystal X-ray structure analysis of compounds [C12C12Tr][Br] and [C12C5Tr][Br] reveal that the cations adopt a U-shaped conformation with head-to-head arranged triazolium cores. In contrast, for [C12C1Tr][Br], a rod like shape of the cation with interdigitated alkyl chains is found. All investigated compounds are thermotropic liquid crystals. Higher ordered smectic phases, smectic C as well as smectic A phases were found depending on the chain length of the cation. Moreover, the clearing point temperature decreases with decreasing chain length with exception for the n-dodecyl-3-alkyltrizoliumbromides with the two shortest alkyl chains, [C12C2Tr][Br] and [C12C1Tr][Br], which present higher clearing temperatures (86 and 156 °C) and are structurally distinctly different.},
doi = {10.1039/c4ra14961k},
journal = {RSC Advances},
number = 22,
volume = 5,
place = {United States},
year = {2015},
month = {1}
}

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    • The Journal of Organic Chemistry, Vol. 75, Issue 12
    • DOI: 10.1021/jo100618d

    A Novel Modular Approach to Triazole-Functionalized Phthalocyanines Using Click Chemistry
    journal, January 2009

    • Juríček, Michal; Kouwer, Paul H. J.; Rehák, Juraj
    • The Journal of Organic Chemistry, Vol. 74, Issue 1
    • DOI: 10.1021/jo802078f

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