Synthesis and liquid crystalline behavior of hydrazide-functionalized triphenylenedicarboxyimides

Seven hydrazide-functionalised triphenylenedicarboxyimides (TDIs) which contain a benzamide group bearing different polar substitutes connected to the imide N atom have been studied with the aim to establish the effect of hydrogen bonding and polar substituents on their mesomorphism properties. Six...

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Published inLiquid crystals Vol. 49; no. 5; pp. 719 - 730
Main Authors Du, Yu, Zhao, Cai-Li, Fan, Sheng-Yuan, Yu, Wen-Hao, Xiang, Shi-Kai, Zhao, Ke-Qing, Feng, Chun, Wang, Bi-Qin
Format Journal Article
LanguageEnglish
Published Abingdon Taylor & Francis 09.04.2022
Taylor & Francis Ltd
Subjects
Benzamide
Benzene
Bonding strength
columnar phase
Crystal structure
Crystallinity
Dipole moments
High temperature
hydrazide-functionalised
Hydrazides
Hydrogen bonding
Liquid crystals
Low temperature
Mesophase
Self-assembly
Temperature dependence
Triphenylenedicarboxyimide
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Summary:Seven hydrazide-functionalised triphenylenedicarboxyimides (TDIs) which contain a benzamide group bearing different polar substitutes connected to the imide N atom have been studied with the aim to establish the effect of hydrogen bonding and polar substituents on their mesomorphism properties. Six of seven hydrazides each form two types of hexagonal columnar liquid crystalline (LC) phase, including a low-temperature Col ho phase and a high-temperature Col hd phase, which were confirmed by characteristic pseudo focal conic fan-shaped textures and XRD measurements. Temperature-dependent FT-IR studies indicated that hydrogen bonding is not strong enough to exist in the LC phases of these hydrazides and disfavours the stabilisation of the columnar mesophase. Nevertheless, dipole-dipole effects were found to favour the mesophase stabilities of these compounds, and the position of the lateral substituent attached to the end benzene ring has a significant impact on the self-assembly by affecting the overall dipole moment.
ISSN:0267-8292
1366-5855
DOI:10.1080/02678292.2021.2006811