Hydroxyl–yne click polymerization: a facile strategy toward poly(vinyl amino ether ester)s with color-tunable luminescence

Jiang, Qimin; Zhang, Hongyan; Jiang, Qilin; Zhang, Shuyi; Guan, Shuyi; Huang, Wenyan; Xue, Xiaoqiang; Yang, Hongjun; Jiang, Li; Jiang, Bibiao; Komarneni, Sridhar

doi:10.1039/d2py01581a

Cited by 15 publications

(8 citation statements)

References 73 publications

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“…For example, very recently, Jiang and coworkers found that self-catalyzed hydroxyl-yne click polymerization could be realized in the presence of tertiary amine-containing alcohols, which could serve as both monomers and internal bases during the polymerization process. [123,124] The introduction of nitrogen atoms into alcohol monomers allows this polymerization to occur without an external base catalyst. Furthermore, activated alkynes mentioned above generally result in the partially conjugated polymers by X-yne click polymerizations.…”

Section: Monomer Scope Expansionmentioning

confidence: 99%

X‐yne click polymerization

Qin

Tang

2023

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Alkyne‐based click polymerizations have been nurtured into a powerful synthetic technique for the preparation of new polymers with advanced structures and versatile properties. Among them, the emerging thiol‐yne, hydroxyl‐yne, and amino‐yne click polymerizations have made remarkable progress from reactions to applications. These polymerizations avoid the usage of inherently dangerous monomers and are safer to operate than the classical azide‐alkyne click polymerization (AACP), making them more prospective for diverse applications. To greatly promote the new alkyne‐based click polymerizations beyond AACP, a new concept of “X‐yne click polymerization” is proposed to unify them, where “X” denotes the monomers that can react with alkynes under mild reaction conditions, including thiols, alcohols, amines, and other promising ones. In this review, we mainly present a brief account of the progress of X‐yne click polymerization and discuss in detail the challenges and opportunities in this field.

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Section: Monomer Scope Expansionmentioning

confidence: 99%

X‐yne click polymerization

Qin

Tang

2023

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“…When the carbon chain length of the diacrylates was shortened, the gaps between HOMOs and LUMOs became smaller, which contributed to the fluorescence red‐shift. Therefore, the tunable fluorescence might be ascribed to the distance of the tertiary amine and alkenyls (Figure 15b) [103].…”

Section: Polymerization‐induced Emission Without Aromatic Ringsmentioning

confidence: 99%

Recent progress on polymerization‐induced emission

Li,

Feng,

Wang

et al. 2023

Luminescence

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The aggregate luminescence behaviors of polymeric luminescent materials have been attracting great attention. However, the importance of the polymerization process on luminescence, namely, polymerization‐induced emission (PIE), has rarely been overviewed. In this review, recent advances in polymerization with PIE effects are summarized, including PIE with aromatic rings based on one‐/two‐/multi‐component polymerizations, and PIE without aromatic rings according to disparate mechanisms of polymerizations. Typical examples are selected to elaborate the basic design principles, as well as the properties and potential applications of the luminous polymers. Moreover, the challenges and perspectives in this area are also discussed.

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“…In this system, the tertiary amines incorporated in the structure of diol monomers act as catalysts. 58 Hence, we hypothesize that through careful selection of functional hydroxyl and activated alkyne monomers, a diverse array of valuable materials can be synthesized to contribute to the advancement of our sustainable society.…”

Section: ■ Introductionmentioning

confidence: 99%

“…More recently, Jiang, Komarneni, and co-workers have developed novel tertiary-amine-containing diol monomers capable of polymerizing with activated alkynes with no need for additional organocatalysts or solvents. In this system, the tertiary amines incorporated in the structure of diol monomers act as catalysts . Hence, we hypothesize that through careful selection of functional hydroxyl and activated alkyne monomers, a diverse array of valuable materials can be synthesized to contribute to the advancement of our sustainable society.…”

Section: Introductionmentioning

confidence: 99%

Harnessing Activated Alkyne-Hydroxyl “Click” Chemistry for Degradable and Self-Healing Poly(urea vinyl ether ester)s

Maity,

Chen,

Wilson-Faubert

et al. 2023

Macromolecules

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The growing impact of polymers in modern-day applications necessitates the development of novel polymeric materials with versatile properties derived from readily available chemicals by employing experimentally simple and efficient polymerization techniques. The "click" reaction between activated alkynes and heteronucleophiles has emerged as a transition-metal catalyst-free, mild, and facile approach to synthesize a wide range of valuable polymeric materials. Interestingly, despite the abundance of hydroxyl groups in organic molecules, their weak nucleophilicity has resulted in their underutilization in "click" reactions. Herein, we harness the potential of hydroxyl nucleophiles for the "click" reaction with activated alkynes, leading to the development of a distinct class of polyureas (PUs) referred to as poly(urea vinyl ether ester)s (PUVEE)s. Utilizing systematically optimized mild polymerization conditions, we successfully obtained thermally stable PUVEEs, soluble in common polar organic solvents, exhibiting weight-average molecular weights of up to 14,000 g mol −1 . The current activated alkyne-hydroxyl "click" polymerization approach represents a sustainable, isocyanate (functional group with high toxicity)-free method for PU synthesis, wherein the commodity chemical urea serves as the direct source of urea functionality. Moreover, tuning the spacer chain length and the density of urea hydrogen bonds in the polymer backbone imparts diverse features to the developed PUVEEs, ranging from high stiffness to stretchability, with intriguing capacity for room-temperature self-healability. Additionally, the incorporated vinyl ether and ester functionalities contribute to the degradability of our PUVEEs into small molecules or oligomers under acidic conditions. Consequently, this class of PUs demonstrates high relevance in promoting sustainability through material reprocessability, via their self-healing property, and reduced environmental impact thanks to their degradability.

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Hydroxyl–yne click polymerization: a facile strategy toward poly(vinyl amino ether ester)s with color-tunable luminescence

Abstract: In this research, we developed a facile and environmentally friendly hydroxyl-yne click polymerization for preparing color-tunable unconventional fluorescent polymers, this polymerization could be performed under mild conditions without external catalyst...

Cited by 15 publications

References 73 publications

X‐yne click polymerization

X‐yne click polymerization

Recent progress on polymerization‐induced emission

Harnessing Activated Alkyne-Hydroxyl “Click” Chemistry for Degradable and Self-Healing Poly(urea vinyl ether ester)s

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