Recent advances in asymmetric organocatalysis based on helical polymers

Zhou, Li; He, Kaifei; Liu, Na; Wu, Zong‐Quan

doi:10.1039/d2py00483f

Cited by 36 publications

(15 citation statements)

References 76 publications

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“…recent years, many groups including Suginome, Yashima, Gellman, and others have reported helical polymers in the application of asymmetric catalysts. [51,[186][187][188][189][190][191][192][193] Suginome et al reported helical poly(quinoxaline-2,3-diyl)s bearing metal-binding sites could be used as chiral ligands for asymmetric hydrosilylation of styrenes, due to the high purity for a one-handed screw sense and stability. [186] Subsequently, the same group synthesized a similar polymer-based catalyst by "Majority-Rules".…”

Section: Chiral Liquid-crystalline Elastomermentioning

confidence: 99%

Supramolecular chiral polymeric aggregates: Construction and applications

et al. 2022

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Inspired by the mystery of natural homochirality, the design and construction of artificial chiral systems with special functions including mechanics, chiroptical devices, and chiral separation have aroused the great interest of scientists. Due to its diverse conformations and components, polymers become an excellent candidate to construct artificial chiral aggregates, which provides an opportunity to fabricate advanced chiral materials. Herein, in this review, we summarized not only the different strategies for construction and regulation of supramolecular chirality in chiral or achiral polymer systems, mainly including post-assembly and polymerizationinduced chiral self-assembly in chiral polymer systems and several chirality transfer and induction strategies in achiral polymer systems, but also the formation mechanisms of chiral aggregates by the chirality amplification from the molecular level to supramolecular level. Furthermore, we present the typical applications of chiral polymeric aggregates in circularly polarized light emission, chiral recognition and separation, and chiral elastomer. Finally, the current challenges and future directions of chiral polymeric aggregates are also elaborated. K E Y W O R D S aggregates, chiral applications, chiral assembly, chirality, polymers INTRODUCTION OF CHIRALITY Chirality in diverse scalesIn nature, chiral structures are widespread at various hierarchical levels, such as the chiral amino acid molecules, the double-helical structure of DNA biomacromolecules, the helical shape of bacterial flagella, and even the visible plant cane and galaxy (Figure 1). [1,2] Scientists have also been working on mimicking helical phenomena in nature and exploring the mechanism of chiral information transfer and amplification, so as to reveal the origin of life and develop advanced functional materials. [3][4][5][6] According to the assembling structures of chiral substances at the molecular level and above, chirality can generally be divided into molecular chirality, supramolecular chirality, and macrochirality, which isThis is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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Section: Chiral Liquid-crystalline Elastomermentioning

confidence: 99%

Supramolecular chiral polymeric aggregates: Construction and applications

et al. 2022

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“…Bio(macro) molecules, for example, nucleic acids, polysaccharides, and amino acids, adopt chiral structure with sophisticated functions. Such biological systems have inspired scientists to design and construct artificial chiral materials for the applications of separation, [1][2][3][4] catalysis, [5][6][7] and sensing, [8][9][10] etc. [11][12][13][14] To be specific, researchers have approached chiral matter in terms of their photophysical properties, including circular dichroism (CD) and circularly polarized luminescence (CPL) which provide chiral information in ground and excited states, respectively.…”

Section: Introductionmentioning

confidence: 99%

Polymer‐Based Circularly Polarized Luminescent Materials

Zhong

Zhao

Deng

2023

Advanced Optical Materials

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Chiral materials capable of generating circularly polarized luminescence (CPL) have gained rapidly growing research interest by virtue of their peculiar photophysical characteristics and far‐reaching applications. Amongst various CPL materials, polymer‐based CPL materials have constituted an important class owing to their abundant types, ease of manufacture, high thermal stability, as well as, tunable properties. The present work reviews the latest advances in constructing polymer‐based CPL materials, which are classified based on the interaction modes between chiral and luminescent components, that is, covalent interaction, non‐covalent interaction, as well as, without covalent and non‐covalent interactions. The newly emerging categories of polymer‐based CPL materials, that is, nonconventional fluorescence‐based CPL materials, circularly polarized room temperature phosphorescence, and polymer‐based CPL materials with thermally activated delayed fluorescence properties are also presented. Typical applications of the polymer‐based CPL emitters in organic light‐emitting diodes, information security encryption, and optical sensors are further discussed. Additionally, the current challenges and future perspectives in this field are summarized. This review article is expected to stimulate more unprecedented achievements derived from polymer‐based CPL materials, thus further promoting their future practical applications.

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“…The helix is an essential secondary structure in biomacromolecules and ubiquitous in nature, − playing an important role in living systems. Inspired by nature, scientists, especially chemists, have designed and prepared various helical polymers. − Among them, helical poly(phenyl isocyanide)s (PPIs) exhibit a stable helical structure and have attracted great attention because of their wide applications in chiral separation, chiral recognition, asymmetric catalysis, etc. − PPIs are commonly prepared using Ni(II), Rh(III), or Pd(II) complexes. − Among them, Pd(II) complexes are air-stable and highly active. Because the Pd(0)/ t -Bu 3 P system can initiate the polymerization of relevant fluorine monomers to afford Pd(II)-terminated PF, this Pd(II)-containing PF could be expected to serve as a catalyst for the polymerization of phenyl isocyanide monomers, rendering functional PF- b -PPI copolymers, exhibiting distinctive optical properties and self-assembly behavior.…”

Section: Introductionmentioning

confidence: 99%

Polyfluorene-block-poly(phenyl isocyanide) Copolymers: One-Pot Synthesis, Helical Assembly, and Circularly Polarized Luminescence

et al. 2023

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Optically active π-conjugated block copolymers are of considerable significance and interest, but their controlled synthesis and helical self-assembly remain challenging. In this study, π-conjugated block copolymers consisting of polyfluorene (PF) and poly(phenyl isocyanide) (PPI) segments were facilely prepared in one pot through two sequential polymerizations. First, a Pd(II)terminated PF precursor was synthesized via the Suzuki cross-coupling polymerization of 7-bromo-9,9-dihexylfluorene-2-boronic acid pinacol ester, which was catalyzed using a Pd(0)/t-Bu 3 P system. Then, PF-b-PPI copolymers with controlled molar mass and narrow dispersities were fabricated via controlled polymerization of phenyl isocyanide monomers utilizing Pd(II)terminated PF as the catalyst. Benefiting from the π-conjugated structure of the PF block and the helicity of the PPI block, the resulting PF-b-PPI copolymers could self-assemble into single-handed helical nanofibers. In the self-assembly process, chirality was transferred from the helical PPI block to the self-assembled helical nanofibers, thereby endowing them with optical activity and excellent circularly polarized luminescence properties.

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Recent advances in asymmetric organocatalysis based on helical polymers

Abstract: Helical polymers have attracted increasing attentions in recent years because of their extensive applications in many fields inculding chiral recognition and seperation, asymmetric catalysis, circularly polarized luminescence, liquid crystallization and...

Cited by 36 publications

References 76 publications

Supramolecular chiral polymeric aggregates: Construction and applications

Supramolecular chiral polymeric aggregates: Construction and applications

Polymer‐Based Circularly Polarized Luminescent Materials

Polyfluorene-block-poly(phenyl isocyanide) Copolymers: One-Pot Synthesis, Helical Assembly, and Circularly Polarized Luminescence

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