Hydrogelators of cyclotriveratrylene derivatives
Fu Cai1, Jiang-Shan Shen, Jin-He Wang
1Department of Chemistry, College of Chemistry and Chemical Engineering, and the MOE Key Laboratory of Analytical Sciences, Xiamen University, Xiamen, 361005, China.
Organic & Biomolecular Chemistry
|January 4, 2012
Summary
Researchers developed novel rigid cavitand cyclotriveratrylene (CTV) supramolecular hydrogels. These hydrogelators exhibit luminescence, pH-triggered transitions, and stability, advancing hydrogel material design.
Area of Science:
- Supramolecular Chemistry
- Materials Science
Background:
- Development of cavity-based supramolecular hydrogels is limited by the scarcity of suitable hydrogelators.
- Cyclotriveratrylene (CTV) derivatives have shown potential in forming organogels.
Purpose of the Study:
- To create novel rigid cavitand cyclotriveratrylene (CTV) based supramolecular hydrogelators.
- To investigate the properties of these new hydrogelators and their resulting hydrogels.
Main Methods:
- Introduction of deprotonable (-COOH) or protonable (-NH2) terminal groups onto rigid, hydrophobic CTV backbones.
- Formation and characterization of supramolecular hydrogels (CTV-1 and CTV-2).
Main Results:
- Successful synthesis of optically anisotropic supramolecular hydrogels from new CTV hydrogelators.
- Hydrogels exhibit excellent thermostability and high tolerance to strong electrolytes.
- CTV-1 and CTV-2 hydrogels are luminescent and show reversible pH-dependent gel-to-sol and sol-to-gel transitions.
Conclusions:
- The creation of CTV-based hydrogelators demonstrates a viable route for developing advanced supramolecular hydrogels.
- Balancing hydrophilic and hydrophobic characteristics in gelator molecules is crucial for designing effective hydrogelators.
Related Concept Videos
01:20Aldehydes and Ketones with Water: Hydrate Formation
An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
01:26Thermal and Photochemical Electrocyclic Reactions: Overview
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
01:20Types of Step-Growth Polymers: Polyesters
The introduction of polyesters has brought major development to the textile industry. The wrinkle-free behavior of polyester blends has eliminated the need for starching and ironing clothes.
Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the polymer...
Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the polymer...
01:18Aromatic Hydrocarbon Cations: Structural Overview
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Removing one hydrogen from the intervening CH2 group with both...
01:20Anionic Chain-Growth Polymerization: Overview
The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...