Related Experiment Video
Updated: Jun 28, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Boron-Catalyzed C1 Copolymerization of Arsonium and Sulfoxonium Ylides toward Unrepresented Structures and
Mingtao Zhou1, Nikos Hadjichristidis1
1Polymer Synthesis Laboratory, KAUST Catalysis Center, Physical Sciences and Engineering Division, King Abdullah University of Science and y (KAUST), Thuwal, 23955, Kingdom of, Saudi Arabia.
Abstract:
The first synthesis of well-defined poly(methylene-co-1,1-diphenylpropenenylene) (C1-co-C1'), equivalent to poly(ethylene-co-diphenylbutadiene) copolymers was accomplished by C1 copolymerization of novel diphenylpropenyl triphenyl arsonium ylides (Ph2AY) and dimethylsulfoxonium methylide (Me2SY) using B-thexylborepane as initiator. All polymerization conditions, including feed ratio, temperature, and reaction time, were optimized. A series of photoluminescent poly(ethylene-co-diphenylbutadiene)s were synthesized at different feed ratios, opening a new synthetic horizon for poly(ethylene-co-disubstitutedbutadiene) copolymers. Notably, a new C1 segment, arising from a double bond rearrangement, was confirmed by NMR, resulting in an unprecedented two-monomer three-structure random terpolymer. An unexpected red-shift phenomenon in the fluorescence spectra was observed with increasing the ratio of Ph2AY in the copolymer. This shift is attributed to the aggregation of diphenylbutadiene segment, similar to through-space conjugation (TSC), likely induced by a decrease in the crystallinity of copolymers. Furthermore, another disubstituted allylic triphenyl arsonium ylides, (E)-2-phenylbutenyl triphenyl arsonium ylide (MePhAY) was also synthesized and investigated. These additional compounds expand the knowledge and the potential applications of such copolymerization techniques in advanced materials.
More Related Videos
09:58Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
08:51Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Related Concept Videos
Cationic Chain-Growth Polymerization: Mechanism
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...