Preparation of efficient organogelators based on pyrazine-2,5-dicarboxylic acid showing room temperature mesophase

A new series of 3,6-dimethyl-pyrazine-2,5-dicarboxylic acid derivatives were synthesized and both their gelation abilities and thermotropic properties were studied. These compounds are efficient organogelators and easily form stable gels in many organic solvents. Moreover, they are room temperature...

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Published inTetrahedron Vol. 71; no. 21; pp. 3221 - 3230
Main Authors Huang, Yaodong, Yuan, Yuqin, Tu, Wei, Zhang, Yan, Zhang, Meijie, Qu, Hongmei
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 27.05.2015
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Abstract A new series of 3,6-dimethyl-pyrazine-2,5-dicarboxylic acid derivatives were synthesized and both their gelation abilities and thermotropic properties were studied. These compounds are efficient organogelators and easily form stable gels in many organic solvents. Moreover, they are room temperature liquid crystals, which all show hexagonal columnar mesophase. Results of 1H nuclear magnetic resonance (1H NMR), Fourier transform infrared spectroscopy (FTIR) and ultra-violet-visible spectroscopy (UV) showed the driving forces of gelation are intra-hydrogen bonding, π–π stacking and van der Waals interaction. On the other hand, the intra-hydrogen bonding may be essential to the formation of mesophase. A Teas plot was constructed to estimate the gel formation of four synthesized pyrazinecarboxamides in organic solvents. [Display omitted]
AbstractList A new series of 3,6-dimethyl-pyrazine-2,5-dicarboxylic acid derivatives were synthesized and both their gelation abilities and thermotropic properties were studied. These compounds are efficient organogelators and easily form stable gels in many organic solvents. Moreover, they are room temperature liquid crystals, which all show hexagonal columnar mesophase. Results of 1H nuclear magnetic resonance (1H NMR), Fourier transform infrared spectroscopy (FTIR) and ultra-violet-visible spectroscopy (UV) showed the driving forces of gelation are intra-hydrogen bonding, π–π stacking and van der Waals interaction. On the other hand, the intra-hydrogen bonding may be essential to the formation of mesophase. A Teas plot was constructed to estimate the gel formation of four synthesized pyrazinecarboxamides in organic solvents. [Display omitted]
A new series of 3,6-dimethyl-pyrazine-2,5-dicarboxylic acid derivatives were synthesized and both their gelation abilities and thermotropic properties were studied. These compounds are efficient organogelators and easily form stable gels in many organic solvents. Moreover, they are room temperature liquid crystals, which all show hexagonal columnar mesophase. Results of H-1 nuclear magnetic resonance (H-1 NMR), Fourier transform infrared spectroscopy (FTIR) and ultra-violet-visible spectroscopy (UV) showed the driving forces of gelation are intra-hydrogen bonding, pi-pi stacking and van der Waals interaction. On the other hand, the intra-hydrogen bonding may be essential to the formation of mesophase. A Teas plot was constructed to estimate the gel formation of four synthesized pyrazinecarboxamides in organic solvents. (C) 2015 Elsevier Ltd. All rights reserved.
A new series of 3,6-dimethyl-pyrazine-2,5-dicarboxylic acid derivatives were synthesized and both their gelation abilities and thermotropic properties were studied. These compounds are efficient organogelators and easily form stable gels in many organic solvents. Moreover, they are room temperature liquid crystals, which all show hexagonal columnar mesophase. Results of 1H nuclear magnetic resonance (1H NMR), Fourier transform infrared spectroscopy (FTIR) and ultra-violet-visible spectroscopy (UV) showed the driving forces of gelation are intra-hydrogen bonding, π–π stacking and van der Waals interaction. On the other hand, the intra-hydrogen bonding may be essential to the formation of mesophase. A Teas plot was constructed to estimate the gel formation of four synthesized pyrazinecarboxamides in organic solvents.
Author Tu, Wei
Yuan, Yuqin
Huang, Yaodong
Zhang, Yan
Qu, Hongmei
Zhang, Meijie
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Keywords Stimuli responsive
Organogelator
Mesophase
Pyrazinecarboxamide
Self-assemble
GELATORS
PHASE
GELS
HANSEN SOLUBILITY PARAMETERS
GELATION
DERIVATIVES
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  start-page: 333
  year: 2008
  ident: WOS:000255373800010
  article-title: Synthesis and liquid crystalline properties of hydrazide derivatives: hydrogen bonding, molecular dipole, and smectic structures
  publication-title: LIQUID CRYSTALS
  doi: 10.1080/02678290801902556
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Snippet A new series of 3,6-dimethyl-pyrazine-2,5-dicarboxylic acid derivatives were synthesized and both their gelation abilities and thermotropic properties were...
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SubjectTerms ambient temperature
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
Fourier transform infrared spectroscopy
gelation
gels
liquid crystals
Mesophase
nuclear magnetic resonance spectroscopy
organic compounds
Organogelator
Physical Sciences
Pyrazinecarboxamide
Science & Technology
Self-assemble
solvents
Stimuli responsive
van der Waals forces
Title Preparation of efficient organogelators based on pyrazine-2,5-dicarboxylic acid showing room temperature mesophase
URI https://dx.doi.org/10.1016/j.tet.2015.04.010
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