Molecular Design, Supramolecular Assembly, and Excellent Dye Adsorption Capacity of Natural Rigid Dehydroabietic Acid-Tailored Amide Organogelators

Abstract

It is very appealing to synthesize functional soft materials from natural and abundant plant diterpenes because they have conformationally rigid and chiral properties. Herein, dehydroabietic-based monoamide (DA-1) and diamide (DA-2) were designed by introducing device interactions, π–π stacking and hydrogen bonding, with an aromatic group, CO, and N–H. DA-1 and DA-2 can be gelled in a mixed solvent and a single solvent, respectively. Several novel supramolecular organic gels including highly entangled three-dimensional networks composed of rods or fibers were constructed. Interestingly, DA-2 forms a helical structure that is right-handed under the cooperative control of the solvent and the rigid structure of rosin. Gel formation was primarily driven by hydrogen bonding, π–π stacking, and van der Waals force. Combined with Gaussian calculation and X-ray diffraction (XRD), we established pack patterns for each system, revealing the roles played by rosin and amide groups. Moreover, the carbon tetrachloride gel of DA-2 can effectively remove Congo red in an aqueous solution, and the removal rate can reach 98.4%. This research explores an efficient organic gel for adsorbing Congo red dye with the secretions of pine trees.

Design and Properties of Novel Hydrophobic Natural Tea Saponin and Its Organogels

“…The gelation mechanism of physical gels formed by relying on non-covalent bonds is different from that of chemical gels. Physical gels are formed mainly by the self-assembly After selecting the appropriate strain, the test of the elastic modulus G ′ , the viscous modulus G ′′ , and the variation with shear frequency of the DC-TS organogel was started using the oscillation mode [21]. As shown in Figure 6, in the 0.1-50 Hz range of shear frequency [21,22], the modulus of the gel system did not change significantly with the change in the shear frequency, and the elastic modulus G ′ of the samples were all larger than their viscous modulus G ′′ , showing typical elastic fluid properties with elastic modulus values of about 7800 Pa and viscous modulus values of about 3700 Pa.…”

“…Physical gels are formed mainly by the self-assembly After selecting the appropriate strain, the test of the elastic modulus G ′ , the viscous modulus G ′′ , and the variation with shear frequency of the DC-TS organogel was started using the oscillation mode [21]. As shown in Figure 6, in the 0.1-50 Hz range of shear frequency [21,22], the modulus of the gel system did not change significantly with the change in the shear frequency, and the elastic modulus G ′ of the samples were all larger than their viscous modulus G ′′ , showing typical elastic fluid properties with elastic modulus values of about 7800 Pa and viscous modulus values of about 3700 Pa. When the shear frequency reached 50 Hz, the intersection of the elastic modulus G ′ and the viscous modulus G ′′ occurred, the elastic modulus G ′ was smaller than its viscous modulus G ′′ , and the organogel network was disrupted and changed from an elastomeric to a viscous flow state.…”

“…If the liquid in the vial stops flowing and becomes solid, it means that the gel has formed. In order to select the gel solvent more accurately, the concentration of forming gel was set as 3 times that in the literature [21], that is, 15 wt%.…”

Self-Assembly of a Series of Carbazole-Based Vinyl-benzoxazole Derivatives in Gel Phases

“…UV−vis absorption, fluorescence spectra, various microscopes (including scanning and transmission electron microscope and atom force and scanning tunneling microscope), and powder X-ray diffraction (PXRD) patterns were used to explore the detailed stacking. 29,30 The PXRD pattern can give information on the periodicity of the intermolecular packing, so it always acts a powerful tool to clarify the approximate long-range ordered packing model in the gels. However, speculative models are crude and sometimes unreliable.…”

“…So, the detailed stacking models of gelators are always needed. UV–vis absorption, fluorescence spectra, various microscopes (including scanning and transmission electron microscope and atom force and scanning tunneling microscope), and powder X-ray diffraction (PXRD) patterns were used to explore the detailed stacking. , …”