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Frontiers of Chemical Science and Engineering

Front. Chem. Sci. Eng.    2020, Vol. 14 Issue (6) : 1112-1121     https://doi.org/10.1007/s11705-019-1865-5
RESEARCH ARTICLE
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()
Key Laboratory of Systems Bioengineering (Ministry of Education), School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China
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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.

Keywords supramolecular self-assembly      organogel      liquid crystal      tartaric acid      hydrogen bond     
Corresponding Author(s): Yaodong Huang   
Just Accepted Date: 29 May 2020   Online First Date: 30 July 2020    Issue Date: 11 September 2020
 Cite this article:   
Xin Wang,Wei Cui,Bin Li, et al. Supramolecular self-assembly of two-component systems comprising aromatic amides/Schiff base and tartaric acid[J]. Front. Chem. Sci. Eng., 2020, 14(6): 1112-1121.
 URL:  
http://journal.hep.com.cn/fcse/EN/10.1007/s11705-019-1865-5
http://journal.hep.com.cn/fcse/EN/Y2020/V14/I6/1112
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Xin Wang
Wei Cui
Bin Li
Xiaojie Zhang
Yongxin Zhang
Yaodong Huang
Fig.1  Scheme 1 Chemical structures of 1, 2 and 3.
Solvent 1-TA 2-TA 3-TA
Methanol SP 23.7 PG
Ethanol SP 43.5 38.2
2-Propanol S 32.7 PG
n-Hexanol 53.4 23.7 PG
CH2Cl2 S 52.8 PG
Chloroform S 16.2 (t) S
Carbon tetrachloride PG 52.8 SP
Hexane SP Ins PG
Cyclohexane 26.7 Ins PG
Diethyl ether Ins Ins PG
Petroleum ether Ins Ins SP
Dioxane PG 29.7 PG
Tetrahydrofuran S 11.7 58.2
Acetone PG 19.2 16.3
Ethyl acetate SP 1.5 (t) 33.0
Benzene S 20.7 (t) S
Toluene S 38.9 S
Xylene S 29.7 S
Chlorobenzene S 8.8 (t) S
Pyridine 107.6 52.8 S
Acetonitrile PG 23.7 PG
Triethylamine PG Ins S
N,N-Dimethyl formamide 105.5 14.6 58.2
Tab.1  Gelation properties of the stoichiometric mixtures of 1-TA, 2-TA and 3-TAa)
Fig.2  Plots of Tgel vs. the concentration of 2-TA in a two-component gel system in ethyl acetate (red) and acetone (blue).
Fig.3  SEM images of xerogels obtained from the gels of (a) 2-TA in ethyl acetate, (b) 2-TA in chloroform, (c) 1-TA in n-hexanol, and (d) 3-TA in tetrahydrofuran.
Fig.4  XRD patterns of the xerogels from (a) 1-TA in hexanol, (b) 2-TA in ethyl acetate, (c) 2-TA in chloroform, and (d) 3-TA in tetrahydrofuran.
Fig.5  FT-IR spectra of compound 2 and the xerogel of 2-TA in chloroform.
2 Powder/cm–1 2-TA gel/cm–1 TA Powder/cm–1
u(N–H) 3343 3336
u(C=O) 1681 1692 1730?1720
u(–OH) 3238 3640?3610
u(C=N) 1594 1591
uas(CH2) 2914 2921
us(CH2) 2847 2853
d(N–H) 1524 1507
Tab.2  Typical absorption bands of 2 and 2-TA at three different states
Fig.6  Scheme 2 Proposed hydrogen bonding network of the 2-TA two-component system.
Fig.7  The anion response test of the tetrahydrofuran gel of 2-TA.
Fig.8  Polarized optical micrograph of 2-TA at (a) 181 °C, (b) 165 °C, (c) 85 °C upon cooling from isotropic liquid and (d) 171 °C, (e) 178 °C, (f) 182 °C upon the second heating run.
Fig.9  DSC first cooling run and second heating run of 2-TA.
Procedure Transition Temperature/°C DH/(kcal?mol–1)
Heating Cr→ Sm X 106.50 6.5
Sm X→Sm B 154.45 2.0
Sm B→ I 177.35 3.8
Cooling I→ Sm B 168.87 –3.9
Sm B→Sm X 147.71 –1.9
Sm X→ Cr 90.68 –11.8
Tab.3  Phase transition temperatures and corresponding enthalpy values of 2-TAa)
Fig.10  The variable-temperature powder X-ray diffraction of 2-TA at 130 and 154 °C.
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