Supramolecular self-assembly of two-component systems comprising aromatic amides/Schiff base and tartaric acid

Xin Wang, Wei Cui, Bin Li, Xiaojie Zhang, Yongxin Zhang, Yaodong Huang

PDF(5846 KB)
PDF(5846 KB)
Front. Chem. Sci. Eng. ›› 2020, Vol. 14 ›› Issue (6) : 1112-1121. DOI: 10.1007/s11705-019-1865-5
RESEARCH ARTICLE
RESEARCH ARTICLE

Supramolecular self-assembly of two-component systems comprising aromatic amides/Schiff base and tartaric acid

Author information +
History +

Abstract

The gelating properties and thermotropic behaviors of stoichiometric mixtures of aromatic amides 1, 2, and the aromatic Schiff base 3 with tartaric acid (TA) were investigated. Among the three gelators, 2-TA exhibited superior gelating ability. Mixture 2-TA exhibits a smectic B phase and an unidentified smectic mesophase during both heating and cooling runs. The results of Fourier transform infrared spectroscopy and X-ray diffraction revealed the existence of hydrogen bonding and p-p interactions in 2-TA systems, which are likely to be the dominant driving forces for the supramolecular self-assembly. Additionally, it was established that all of the studied gel self-assemblies and mesophases possess a lamellar structure. The anion response ability of the tetrahydrofuran gel of 2-TA was evaluated and it was found that it was responsive to the stimuli of F, Cl, Br, I, AcO.

Graphical abstract

Keywords

supramolecular self-assembly / organogel / liquid crystal / tartaric acid / hydrogen bond

Cite this article

Download citation ▾
Xin Wang, Wei Cui, Bin Li, Xiaojie Zhang, Yongxin Zhang, Yaodong Huang. Supramolecular self-assembly of two-component systems comprising aromatic amides/Schiff base and tartaric acid. Front. Chem. Sci. Eng., 2020, 14(6): 1112‒1121 https://doi.org/10.1007/s11705-019-1865-5

References

[1]
Bhattacharjee S, Bhattacharya S. Orotic acid as a useful supramolecular synthon for the fabrication of an OPV based hydrogel: stoichiometry dependent injectable behavior. Chemical Communications, 2015, 51(31): 6765–6768
CrossRef Google scholar
[2]
Raeburn J, Adams D J. Multicomponent low molecular weight gelators. Chemical Communications, 2015, 51(25): 5170–5180
CrossRef Google scholar
[3]
Buerkle L E, Rowan S J. Supramolecular gels formed from multi-component low molecular weight species. Chemical Society Reviews, 2012, 41(18): 6089–6102
CrossRef Google scholar
[4]
Liu M H, Quyang G H, Niu D, Sang Y. Supramolecular gelaton: Towards the design of molecular gels. Organic Chemistry Frontiers : An International Journal of Organic Chemistry / Royal Society of Chemistry, 2018, 5(19): 2885–2900
CrossRef Google scholar
[5]
Tu T, Zhu H B, Fang W W, Zhang Y, Wu J J, Liu C. Advance between supramolecular gels and catalysis. Chemistry, an Asian Journal, 2018, 13(7): 712–729
CrossRef Google scholar
[6]
Verma I, Rajeev N, Mohiuddin G, Pal S K. Ordering transitions in liquid crystals triggered by bioactive cyclic amphiphiles: Potential application in label-free detection of amyloidogenic peptides. Journal of Physical Chemistry C, 2019, 123(11): 6526–6536
CrossRef Google scholar
[7]
Kato T, Mizoshita N, Kishimoto K. Functional liquid-crystalline assemblies: Self-organized soft materials. Angewandte Chemie International Edition, 2006, 45(1): 38–68
CrossRef Google scholar
[8]
Wang L Y, Liu S X, Li H M, Huang Y D. Preparation and properties of the two-component hydrogels based on pyrazine dicarboxylic acid and melamine. Chemical Journal of Chinese Universities, 2017, 38(5): 806–813
[9]
Mahapatra R D, Dey J. Instant gels from mixtures of amines and anhydrides at room temperature. Colloids and Surfaces. B, Biointerfaces, 2016, 147: 422–433
CrossRef Google scholar
[10]
Hamaguchi K, Kuo D, Liu M M, Sakamoto T, Yoshio M, Katayama H, Kato T. Nanostructured virus filtration membranes based on two component columnar liquid crystals. ACS Macro Letters, 2019, 8(1): 24–30
CrossRef Google scholar
[11]
Mahalingam T, Venkatachalam T, Jayaprakasam R, Vijayakumar V N. Structural and thermo-optic studies on linear double hydrogen bonded ferroelectric liquid crystal homologous series. Molecular Crystals and Liquid Crystals (Philadelphia, Pa.), 2016, 641(1): 10–24
CrossRef Google scholar
[12]
Yang J H, Christianson L A, Gellman S H. Comparison of an HXH three-center hydrogen bond with alternative two-center hydrogen bonds in a model system. Organic Letters, 1999, 1(1): 11–13
CrossRef Google scholar
[13]
Deebika B, Balamurugan S, Kannan P. Liquid crystalline H-bonded polymers influenced by chiral and achiral spacers. Journal of Polymer Research, 2012, 19(7): 9920–684
CrossRef Google scholar
[14]
Yamaguchi D, Eimura H, Yoshio M, Kato T. Redox-active supramolecular fibers of a nitronyl nitroxide-based gelator. Chemistry Letters, 2016, 45(8): 863–865
CrossRef Google scholar
[15]
Takemoto Y, Uchida Y, Shimono S, Yamauchi J, Tamura R. Preparation and magnetic properties of nitroxide radical liquid crystalline physical gels. Molecular Crystals and Liquid Crystals (Philadelphia, Pa.), 2017, 647(1): 279–289
CrossRef Google scholar
[16]
Huang Y, Zhang X, Cui W, Wang X, Li B, Zhang Y, Yang J. Novel liquid crystalline organogelators based on terephthalic acid and terephthalaldehyde derivatives: Properties and promotion through the formation of halogen bonding. New Journal of Chemistry, 2020, 44(2): 614–625
CrossRef Google scholar
[17]
Bao C Y, Lu R, Jin M, Xue P C, Tan C H, Liu G F, Zhao Y. Zhao Y Y. L-Tartaric acid assisted binary organogel system: Strongly enhanced fluorescence induced by supramolecular assembly. Organic & Biomolecular Chemistry, 2005, 3(14): 2508–2512
CrossRef Google scholar
[18]
Huang Y D, Yuan Y Q, Tu W, Zhang Y, Zhang M J, Qu H M. Preparation of efficient organogelators based on pyrazine-2,5-dicarboxylic acid showing room temperature mesophase. Tetrahedron, 2015, 71(21): 3221–3230
CrossRef Google scholar
[19]
Shishido Y, Anetai H, Takedam T, Hoshino N, Noro S, Nakamura T, Akutagawa T. Molecular assembly and ferroelectric response of benzenecarboxamides bearing multiple ‒CONHC14H29 chains. Journal of Physical Chemistry C, 2014, 118(36): 21204–21214
CrossRef Google scholar
[20]
Feng G L, Chen H H, Cai J H, Wen J W, Liu X B. L-Phenylalanine based low-molecular-weight efficient organogelators and their selective gelation of oil from oil/water mixtures. Soft Materials, 2014, 12(4): 403–410
CrossRef Google scholar
[21]
Yamanaka M, Aoyama R. Construction of two- or three-component low molecular weight gel systems. Bulletin of the Chemical Society of Japan, 2010, 83(7): 1127–1131
CrossRef Google scholar
[22]
Xue P C, Zhang Y, Jia J H, Xu D F, Zhang X F, Liu X L, Zhou H P, Zhang P, Lu R, Takafuji M, Ihara H. Solvent-dependent photophysical and anion responsive properties of one glutamide gelator. Soft Matter, 2011, 7(18): 8296–8304
CrossRef Google scholar
[23]
Cao X H, Zhao N, Lv H T, Gao A P, Shi A P, Wu Y Q. 4-Nitrobenzene thiourea self-assembly system and its transformation upon addition of Hg2+ ion: Applications as sensor to fluoride ion. Sensors and Actuators. B, Chemical, 2018, 266: 637–644
CrossRef Google scholar
[24]
Huang Y D, Liu S X, Xie Z F, Sun Z P, Chai W, Jiang W. Novel 1,2,3-triazole-based compounds: Iodo effect on their gelation behavior and cation response. Frontiers of Chemical Science and Engineering, 2018, 12(2): 252–261
CrossRef Google scholar
[25]
Gao A P, Li Y R, Lv H T, Liu D, Zhao N, Ding Q Q, Gao X H. Melamine tunable effect in a lenalidomide-based supramolecular self-assembly system via hydrogen bonding. New Journal of Chemistry, 2017, 41(16): 7924–7931
CrossRef Google scholar
[26]
Kaczmarczyk B. FTi.r. study of hydrogen bonds in aliphatic polyesteramides. Polymer, 1998, 39(23): 5853–5860
CrossRef Google scholar
[27]
Hermansson K. Blue-shifting hydrogen bonds. Journal of Physical Chemistry A, 2002, 106(18): 4695–4702
CrossRef Google scholar
[28]
Ghosh S, Goswami K, Ghosh K. Pyrrole-based tetra-amide for hydrogen pyrophosphate (HP2O73-) and F- ions in sol-gel medium. Supramolecular Chemistry, 2017, 29(12): 946–952
CrossRef Google scholar
[29]
Lin Q, Zhu X, Fu Y P, Zhang Y M, Fang R, Yang L Z, Wei T B. Rationally designed anion-responsive-organogels: Sensing F via reversible color changes in gel-gel states with specific selectivity. Soft Matter, 2014, 10(31): 5715–5723
CrossRef Google scholar
[30]
Song H H, Yoo J H, Doe J K, Lee K S, Choi Y K, Keum S R. Liquid crystal structures of spirobenzopyram derivatives. Molecular Crystals and Liquid Crystals (Philadelphia, Pa.), 2000, 349(1): 267–270
[31]
Marzec M, Popczyk J, Fąfara A, Wróbel S, Dąbrowski R. Antiferroelectric liquid crystals studied by differential scanning calorimetry and electrooptic methods. Ferroelectrics, 2002, 281(1): 123–134
CrossRef Google scholar

Acknowledgements

This work was supported by the Natural Science Foundation of Tianjin (No. 15JCYBJC20100).

RIGHTS & PERMISSIONS

2020 Higher Education Press
AI Summary AI Mindmap
PDF(5846 KB)

Accesses

Citations

Detail

Sections
Recommended

/