Impact of Substitution Pattern and Chain Length on the Thermotropic Properties of Alkoxy-Substituted Triphenyl-Tristriazolotriazines

Impact of Substitution Pattern and Chain Length on the Thermotropic Properties of Alkoxy-Substituted Triphenyl-Tristriazolotriazines

Tristriazolotriazines (TTTs) with a threefold alkoxyphenyl substitution were prepared and studied by DSC, polarized optical microscopy (POM) and X-ray scattering. Six pentyloxy chains are sufficient to induce liquid-crystalline behavior in these star-shaped compounds. Thermotropic properties of TTTs...

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Main Authors: Thorsten Rieth, Natalie Tober, Daniel Limbach, Tobias Haspel, Marcel Sperner, Niklas Schupp, Philipp Wicker, Stefan Glang, Matthias Lehmann, Heiner Detert
Format: Article
Language:English
Published: MDPI AG 2020-12-01
Series:Molecules
Subjects:
star-shaped compounds
discotic liquid crystals
X-ray diffraction
differential scanning calorimetry
polarizing optical microscopy
swallow-tail
Online Access:https://www.mdpi.com/1420-3049/25/23/5761
id doaj-6026965e383f4d22808985d342771b66
record_format Article
spelling doaj-6026965e383f4d22808985d342771b662020-12-08T00:01:44ZengMDPI AGMolecules1420-30492020-12-01255761576110.3390/molecules25235761Impact of Substitution Pattern and Chain Length on the Thermotropic Properties of Alkoxy-Substituted Triphenyl-TristriazolotriazinesThorsten Rieth0Natalie Tober1Daniel Limbach2Tobias Haspel3Marcel Sperner4Niklas Schupp5Philipp Wicker6Stefan Glang7Matthias Lehmann8Heiner Detert9Department for Chemistry, Johannes Gutenberg-University, 55099 Mainz, GermanyDepartment for Chemistry, Johannes Gutenberg-University, 55099 Mainz, GermanyDepartment for Chemistry, Johannes Gutenberg-University, 55099 Mainz, GermanyDepartment for Chemistry, Johannes Gutenberg-University, 55099 Mainz, GermanyDepartment for Chemistry, Johannes Gutenberg-University, 55099 Mainz, GermanyDepartment for Chemistry, Johannes Gutenberg-University, 55099 Mainz, GermanyDepartment for Chemistry, Johannes Gutenberg-University, 55099 Mainz, GermanyDepartment for Chemistry, Johannes Gutenberg-University, 55099 Mainz, GermanyInstitute for Organic Chemistry, Julius-Maximilians-University, 97074 Würzburg, GermanyDepartment for Chemistry, Johannes Gutenberg-University, 55099 Mainz, GermanyTristriazolotriazines (TTTs) with a threefold alkoxyphenyl substitution were prepared and studied by DSC, polarized optical microscopy (POM) and X-ray scattering. Six pentyloxy chains are sufficient to induce liquid-crystalline behavior in these star-shaped compounds. Thermotropic properties of TTTs with varying substitution patterns and a periphery of linear chains of different lengths, branching in the chain and swallow-tails, are compared. Generally, these disks display broad and stable thermotropic mesophases, with the tangential TTT being superior to the radial isomer. The structure–property relationships of the number of alkyl chains, their position, length and structure were studied.https://www.mdpi.com/1420-3049/25/23/5761star-shaped compoundsdiscotic liquid crystalsX-ray diffractiondifferential scanning calorimetrypolarizing optical microscopyswallow-tail
collection DOAJ
language English
format Article
sources DOAJ
author Thorsten Rieth
Natalie Tober
Daniel Limbach
Tobias Haspel
Marcel Sperner
Niklas Schupp
Philipp Wicker
Stefan Glang
Matthias Lehmann
Heiner Detert
spellingShingle Thorsten Rieth
Natalie Tober
Daniel Limbach
Tobias Haspel
Marcel Sperner
Niklas Schupp
Philipp Wicker
Stefan Glang
Matthias Lehmann
Heiner Detert
Impact of Substitution Pattern and Chain Length on the Thermotropic Properties of Alkoxy-Substituted Triphenyl-Tristriazolotriazines
Molecules
star-shaped compounds
discotic liquid crystals
X-ray diffraction
differential scanning calorimetry
polarizing optical microscopy
swallow-tail
author_facet Thorsten Rieth
Natalie Tober
Daniel Limbach
Tobias Haspel
Marcel Sperner
Niklas Schupp
Philipp Wicker
Stefan Glang
Matthias Lehmann
Heiner Detert
author_sort Thorsten Rieth
title Impact of Substitution Pattern and Chain Length on the Thermotropic Properties of Alkoxy-Substituted Triphenyl-Tristriazolotriazines
title_short Impact of Substitution Pattern and Chain Length on the Thermotropic Properties of Alkoxy-Substituted Triphenyl-Tristriazolotriazines
title_full Impact of Substitution Pattern and Chain Length on the Thermotropic Properties of Alkoxy-Substituted Triphenyl-Tristriazolotriazines
title_fullStr Impact of Substitution Pattern and Chain Length on the Thermotropic Properties of Alkoxy-Substituted Triphenyl-Tristriazolotriazines
title_full_unstemmed Impact of Substitution Pattern and Chain Length on the Thermotropic Properties of Alkoxy-Substituted Triphenyl-Tristriazolotriazines
title_sort impact of substitution pattern and chain length on the thermotropic properties of alkoxy-substituted triphenyl-tristriazolotriazines
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2020-12-01
description Tristriazolotriazines (TTTs) with a threefold alkoxyphenyl substitution were prepared and studied by DSC, polarized optical microscopy (POM) and X-ray scattering. Six pentyloxy chains are sufficient to induce liquid-crystalline behavior in these star-shaped compounds. Thermotropic properties of TTTs with varying substitution patterns and a periphery of linear chains of different lengths, branching in the chain and swallow-tails, are compared. Generally, these disks display broad and stable thermotropic mesophases, with the tangential TTT being superior to the radial isomer. The structure–property relationships of the number of alkyl chains, their position, length and structure were studied.
topic star-shaped compounds
discotic liquid crystals
X-ray diffraction
differential scanning calorimetry
polarizing optical microscopy
swallow-tail
url https://www.mdpi.com/1420-3049/25/23/5761
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AT stefanglang impactofsubstitutionpatternandchainlengthonthethermotropicpropertiesofalkoxysubstitutedtriphenyltristriazolotriazines
AT matthiaslehmann impactofsubstitutionpatternandchainlengthonthethermotropicpropertiesofalkoxysubstitutedtriphenyltristriazolotriazines
AT heinerdetert impactofsubstitutionpatternandchainlengthonthethermotropicpropertiesofalkoxysubstitutedtriphenyltristriazolotriazines
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