Controlled and Regioselective Ring-Opening Polymerization for Poly(disulfide)s by Anion-Binding Catalysis

Du, Tianyi; Shen, Boming; Dai, Jieyu; Zhang, Miaomiao; Chen, Xingjian; Yu, Peiyuan; Liu, Yun

doi:10.1021/jacs.3c10708

Cited by 4 publications

(2 citation statements)

References 97 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…What's more, achieving regionally selective PLA remains challenging due to the highly nucleophilic chain ends of PLA, which may react with S–S bond monomers or polymers to induce chain transfer and chemical irregularities. Du et al 49 addressed this issue using an anion-binding catalyst (Fig. 2H).…”

Section: Rop Polymerization Of La Moleculesmentioning

confidence: 99%

Biological applications of lipoic acid-based polymers: an old material with new promise

Yu,

Fang,

Luan

et al. 2024

J. Mater. Chem. B

View full text Add to dashboard Cite

show abstract

Section: Rop Polymerization Of La Moleculesmentioning

confidence: 99%

Biological applications of lipoic acid-based polymers: an old material with new promise

Yu,

Fang,

Luan

et al. 2024

J. Mater. Chem. B

View full text Add to dashboard Cite

show abstract

“…The precise control of the regiochemical outcome during polymerization is useful for material property tuning and macromolecular assembly. − With this in mind, we proposed a new monomer class, namely, 1-aryl-4-alkylbutatriene ( A ). The electronic difference between an aryl and alkyl group could potentially lead to a predominant HT connectivity.…”

Section: Introductionmentioning

confidence: 99%

Regioselective Condensation Polymerization of Propargylic Electrophiles Enabled by Catalytic Element-Cupration

Wang,

Zhu

2024

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Here, we report a set of new polymerization reactions enabled by the 1,2-regioselective hydro-and silylcupration of enyne-type propargylic electrophiles. Highly regioregular head-to-tail poly(2-butyne-1,4-diyl)s (HT-PBD), bearing either methyl or silylmethyl side chains, are synthesized for the first time. A rapid entry into carbon-rich copolymers with adjustable silicon content is developed via in situ monomer bifurcation. Furthermore, a one-pot polymerization/semireduction sequence is developed to access a cis-poly(butadiene)-derived backbone by a ligand swap on copper hydride species. Interestingly, borocupration, typically exhibiting identical regioselectivity with its hydro-and silyl analogues, seems to proceed in a 3,4-selective manner. Computational studies suggest the possible role of the propargylic leaving group in this selectivity switch. This work presents a new class of regioregular spcarbon-rich polymers and meanwhile a novel approach to organosilicon materials.

show abstract

The Integral Role of Conjugate Acids in Brønsted Base‐Catalyzed Regiodivergent Synthesis

Chen,

Marri,

Lin

2024

ChemCatChem

View full text Add to dashboard Cite

Catalyst‐controlled diversity‐oriented synthesis (CatDOS) is an important research area for expanding molecular complexities and achieving high atomic economics. Plenty of regiodivergent syntheses have been achieved through metal catalysis, covalent and non‐covalent organocatalysis by controlling the molecular recognition function of the catalysts. However, the development of regiodivergent CatDOS through Brønsted base in organocatalysis was relatively less than others. Numerous studies about Brønsted base organocatalysis have demonstrated the powerful molecular recognition abilities of their cationic conjugate acids (CA) mainly in controlling the stereoselectivity instead of the regioselectivity. This concept review aims to conceptualize a new perspective to consider the potential role of the cationic CA of Brønsted bases for regiodivergent CatDOS. Recent representative examples are selected to demonstrate the potential of cationic CA on site‐selectivity control in single‐bond and multiple‐bond formation reactions. The summarized results show that even CA of common tertiary amines, protic ammonium ions, could affect the regioselectivity in the early‐ or late‐stage step during multiple‐bond formation after initial deprotonation. The results also hinted that the properties and ion‐pairing interactions of CA could be more important than the basicity of bases in controlling regioselectivity. Perspectives and hypotheses for explanation of the mechanism of regioselectivity are also included in this review.

show abstract

Controlled and Regioselective Ring-Opening Polymerization for Poly(disulfide)s by Anion-Binding Catalysis

Cited by 4 publications

References 97 publications

Biological applications of lipoic acid-based polymers: an old material with new promise

Biological applications of lipoic acid-based polymers: an old material with new promise

Regioselective Condensation Polymerization of Propargylic Electrophiles Enabled by Catalytic Element-Cupration

The Integral Role of Conjugate Acids in Brønsted Base‐Catalyzed Regiodivergent Synthesis

Contact Info

Product

Resources

About