Adjusting and visualizing the stability of an acyl chloride through the delocalization effect and introducing AIEgens
Lu Liu1, Qing Wan1,2, Chen Gui1
1AIE-institute, State Key Laboratory of Luminescent Materials and Devices, Center for Aggregation-Induced Emission, Key Laboratory of Luminescence from Molecular Aggregates of Guangdong Province, South China University of Technology (SCUT), Guangzhou 510640, China. wangzhiming@scut.edu.cn.
Abstract:
Acyl chloride is an important functional group in acylation reactions, though its compounds are difficult to store and transport due to their high reactivity. In this research, phenanthro[9,10-d]imidazole is introduced into an acyl chloride agent of TPEPCl to enhance the stability via the delocalization effect. Meanwhile, rarely reported acyl chloride crystals have been achieved which could further prove its stability. The tetraphenylethylene group is also employed to visually monitor the changes of TPEPCl via fluorescent variation with the help of aggregation-induced emission (AIE) characteristics. The reactivity of TPEPCl could be stimulated by a strong alkaline solution or high temperature. Crystallography analyses of acyl TPE-PI derivatives are also discussed and the relationship between the delocalization structure and stability is determined. These findings help to stabilize, control and monitor the reactivities of active functional materials for applications.
More Related Videos
Related Concept Videos
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Acid Halides to Amides: Aminolysis
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
Acid Halides to Esters: Alcoholysis
Relative Stabilities of Alkenes
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene


