Barbier polymerization induced emission of cinnamaldehyde: a one-pot Grignard reaction?

Li, Deshan; Sheng, Yuqi; Wu, Liang‐Tao; Chen, Yu-Jiao; Xiao, Hang; Sun, Xiaoli; Bao, Hongli; Wan, Wen‐Ming

doi:10.1039/d2cc04902c

Cited by 13 publications

(7 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Artificial light‐harvesting systems are very attractive, which exhibit potential contributions in the fields of sustainable utilization of energy [8h,14] . Due to the AIE characteristics of PTPE, its self‐quenching effect is suppressed, which reveals that PTPE can be an ideal candidate donor for preparing artificial light‐harvesting systems.…”

Section: Resultsmentioning

confidence: 99%

Barbier Polymerization‐Induced Emission towards Fully Substituted Polyethylene Analogues with Non‐Traditional Intrinsic Luminescence

Xiao,

Shi,

et al. 2023

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

The properties of polyethylene are highly dependent on the variety and quantity of substitutions. Generally, polyethylene can only be fully substituted with fluorine atoms, mainly e. g., polytetrafluoroethylene and nafion, because atomic radius of fluorine atom is small enough. The preparation of fully substituted polyethylene analogues (FSPEA) and their non‐traditional intrinsic luminescence (NTIL) are attractive, especially for substitutions with relatively larger atomic radii than a fluorine atom. Here, Barbier polymerization‐induced emission (PIE) is demonstrated as a universal method for the molecular design of NTIL type FSPEAs with intriguing aggregation‐induced emission (AIE) behaviors. Through Barbier polymerization of diphenyldichloromethane and different peroxyesters in the presence of Mg in one pot, a series of FSPEAs, including polytriphenylethanol (PTPE), polydiphenylfurylethanol (PDPFE), polydiphenylthiophenylethanol (PDPTE) and polydiphenylnaphthylethanol (PDPNE) have been successfully prepared. Further potential applications for explosive detection, artificial light‐harvesting system and white phosphor‐converted light‐emitting diode are investigated. Therefore, this work opens up a new approach for the molecular design of FSPEA with non‐conjugated luminescence, which may cause inspirations to different research fields like polyolefin and luminescent materials.

show abstract

Section: Resultsmentioning

confidence: 99%

Barbier Polymerization‐Induced Emission towards Fully Substituted Polyethylene Analogues with Non‐Traditional Intrinsic Luminescence

Xiao,

Shi,

et al. 2023

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

show abstract

“…So, these results confirm that Barbier CARP is not an anionic polymerization, which also indicate that Barbier reaction could not be regarded as a one-pot Grignard reaction, even though they share very similar formula, similar to our previous reports. 39,44 To reveal the mechanism and behavior of this air Barbier CARP, the polymerization kinetics was studied. When [St]/[i-PrCl] was 5, a linear increase of M n from 5.0 to 20.7 kg/mol vs monomer conversion was observed up to full monomer conversion.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Also, similar to anionic polymerization literature, the Grignard reagent ( i -PrMgCl) could not initiate the polymerization of nonpolar St (Table , entry 8). So, these results confirm that Barbier CARP is not an anionic polymerization, which also indicate that Barbier reaction could not be regarded as a one-pot Grignard reaction, even though they share very similar formula, similar to our previous reports. , …”

Section: Resultsmentioning

confidence: 99%

Compatibility of Barbier Covalent-Anionic-Radical Polymerization with Air and Divinylbenzene

Chen

et al. 2023

Macromolecules

Self Cite

View full text Add to dashboard Cite

The controlled preparation of polymers with narrow molecular weight distribution (Đ) is highly desirable in polymer science, which generally requires relatively rigorous conditions like inert atmosphere, low temperature, or moderate conversion to reduce undesired side reactions and built-in bimolecular termination. Here, the compatibility of Barbier covalent-anionic-radical polymerization (CARP) is demonstrated with air and divinylbenzene (DVB). Through this Barbier CARP in air, narrow distributed polystyrenes with Đ as low as 1.09 are successfully prepared under mild conditions with full monomer conversion. Barbier CARP of DVB enables the preparation of poly(para-divinylbenzene) with Đ of 1.29, which exhibits versatile postpolymerization modification properties. Unpredictably, benzylic hydrogen atom affects this Barbier CARP significantly. This work therefore expands the method library for the preparation of polymers with low Đ, where rigorous conditions are not required.

show abstract

“…[ 2‐16 ] In comparison with traditional luminescent polymer designed by incorporating luminescent moieties into polymer chain through multiple steps, PIE represents a facile and feasible strategy to realize NTIL through different polymerization methods in one pot. [ 12,16‐20 ]…”

Section: Background and Originality Contentmentioning

confidence: 99%

Nucleophilic Substitution Polymerization‐Induced Emission of 1,3‐Dicarbonyl Compounds as a Versatile Approach for Aggregation‐Induced Emission Type Non‐Traditional Intrinsic Luminescence^†

Chen

et al. 2023

Chin. J. Chem.

View full text Add to dashboard Cite

Comprehensive Summary Nucleophilic substitution reaction and 1,3‐dicarbonyl compounds play significant roles in organic chemistry, and non‐traditional intrinsic luminescence (NTIL) has become an emerging research area. Here, we demonstrate the successful nucleophilic substitution polymerization of 1,3‐dicarbonyl compounds, including acetylacetone, 3,5‐heptanedione, methyl acetoacetate, cyclopentane‐1,3‐dione, 1,3‐indandione, 1‐phenyl‐1,3‐butanedione and dibenzoylmethane, where reactive hydrogens at α position of 1,3‐dicarbonyl compounds are involved. Through this base catalyzed nucleophilic substitution polycondensation between 1,3‐dicarbonyl compounds and α,α’‐dibromo xylene, a series of nonconjugated poly(1,3‐dicarbonyl)s have been successfully prepared with high yield (up to >99%) under mild conditions. Investigations reveal that this nucleophilic substitution polycondensation exhibits self‐accelerating effect and flexible stoichiometry characteristics, which exhibits advantages over traditional polycondensation methods. This polymerization also exhibits intriguing polymerization‐induced emission (PIE) characteristics, where nonconjugated poly(1,3‐dicarbonyl)s exhibit intriguing chemical structure dependent aggregation‐induced emission (AIE) type NTIL. This work therefore expands the monomer, method, chemical structure and property libraries of polymer chemistry, which may cause inspirations to polymerization methodology, PIE, AIE and NTIL.

show abstract

Barbier polymerization induced emission of cinnamaldehyde: a one-pot Grignard reaction?

Abstract: The Barbier reaction is generally regarded as a one-pot Grignard reaction. Here, Grignard reaction of cinnamaldehyde is demonstrated to give 1,2-addition product, while Barbier reaction of cinnamaldehyde yields macromolecule with...

Cited by 13 publications

References 35 publications

Barbier Polymerization‐Induced Emission towards Fully Substituted Polyethylene Analogues with Non‐Traditional Intrinsic Luminescence

Barbier Polymerization‐Induced Emission towards Fully Substituted Polyethylene Analogues with Non‐Traditional Intrinsic Luminescence

Compatibility of Barbier Covalent-Anionic-Radical Polymerization with Air and Divinylbenzene

Nucleophilic Substitution Polymerization‐Induced Emission of 1,3‐Dicarbonyl Compounds as a Versatile Approach for Aggregation‐Induced Emission Type Non‐Traditional Intrinsic Luminescence^†

Contact Info

Product

Resources

About

Barbier polymerization induced emission of cinnamaldehyde: a one-pot Grignard reaction?

Abstract: The Barbier reaction is generally regarded as a one-pot Grignard reaction. Here, Grignard reaction of cinnamaldehyde is demonstrated to give 1,2-addition product, while Barbier reaction of cinnamaldehyde yields macromolecule with...

Cited by 13 publications

References 35 publications

Barbier Polymerization‐Induced Emission towards Fully Substituted Polyethylene Analogues with Non‐Traditional Intrinsic Luminescence

Barbier Polymerization‐Induced Emission towards Fully Substituted Polyethylene Analogues with Non‐Traditional Intrinsic Luminescence

Compatibility of Barbier Covalent-Anionic-Radical Polymerization with Air and Divinylbenzene

Nucleophilic Substitution Polymerization‐Induced Emission of 1,3‐Dicarbonyl Compounds as a Versatile Approach for Aggregation‐Induced Emission Type Non‐Traditional Intrinsic Luminescence†

Contact Info

Product

Resources

About

Nucleophilic Substitution Polymerization‐Induced Emission of 1,3‐Dicarbonyl Compounds as a Versatile Approach for Aggregation‐Induced Emission Type Non‐Traditional Intrinsic Luminescence^†