Chiral, fluorescent microparticles constructed by optically active helical substituted polyacetylene: preparation and enantioselective recognition ability

Huang, Huajun; Yang, Wantai; Deng, Jianping

doi:10.1039/c4ra16466k

Cited by 18 publications

(17 citation statements)

References 77 publications

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“…For the achiral polymer (PMF), it formed racemic helical structures and thus no CD signal appeared in the CD spectrum. [40][41][42] Therefore we successfully prepared optically active helical polymers, L-PCMF and D-PCMF, and the optically inactive helical polymer PMF.…”

Section: Synthesis and Characterization Of Chiral Uorescent Nanobersmentioning

confidence: 99%

Electrospinning chiral fluorescent nanofibers from helical polyacetylene: preparation and enantioselective recognition ability

Yang

Zhao

et al. 2020

Nanoscale Adv.

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Chirality is ubiquitous in nature and closely related to the pharmacological effects of chiral drugs. Therefore, chiral recognition of molecular enantiomers becomes an important research theme. Fluorescence detection is highly sensitive and fast but has achieved only limited success in enantiomeric detection due to the lack of powerful chiral fluorescence detection materials. In this paper, a novel chiral fluorescent probe material, i.e. a chiral fluorescent nanofiber membrane, is prepared from chiral helical substituted polyacetylene by the electrospinning technique. The SEM images demonstrate the success in fabricating continuous, uniform nanofibers with a diameter of about 100 nm. Circular dichroism spectra show that the nanofibers exhibit fascinating optical activity. One of the enantiomeric chiral fluorescent membranes has chiral fluorescence recognition effects towards alanine and chiral phenylethylamine, while the other enantiomeric membrane does not. The prepared chiral fluorescent nano-materials are expected to find various applications in chirality-related fields due to their advantages such as chirality, fluorescence, and a high specific surface area. The established preparation approach also promises a potent and versatile platform for developing advanced nanofiber materials from conjugated polymers. † Electronic supplementary information (ESI) available: Structural formula, FT-IR spectra, GPC, electrospinning parameters, SEM images, digital photo of uorescent polymer membranes, CD and UV-vis absorption spectra, and uorescence emission spectra. See

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Section: Synthesis and Characterization Of Chiral Uorescent Nanobersmentioning

confidence: 99%

Electrospinning chiral fluorescent nanofibers from helical polyacetylene: preparation and enantioselective recognition ability

Yang

Zhao

et al. 2020

Nanoscale Adv.

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“…Various kinds of techniques have been proposed to discriminate the molecular chirality on the basis of optical property changes of the host sensors induced by the guest compounds. [21][22][23][24][25][26] However, most of them can only discriminate either central or axial chirality; sensors that can be used for various types of chirality are quite rare. 13,14 Until now, a wide variety of chiral fluorescent sensors have been reported using not only small molecules, such as binaphthyl-, 15, 16 1,8-diheteroarylnaphthalene-, 17,18 helicene- 19 and bis(oxazolinyl)phenol-based compounds, 20 but also synthetic macromolecules.…”

Section: Introductionmentioning

confidence: 99%

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

et al. 2016

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Chiral fluorescent sensors were designed and synthesized from naturally occurring optically active cellulose, in which a terthienyl moiety was used as a fluorescent signaling unit, and their chiral recognition abilities were investigated on the basis of an enantioselective fluorescence response to aromatic nitro compounds as quenchers. A cellulose phenylcarbamate derivative (Ce-1b) exhibited an apparent enantioselectivity for various types of aromatic nitro compounds containing either central or axial chirality. Considering the fact that a corresponding monosaccharide derivative showed almost no enantioselectivity, the chiral recognition ability of the cellulose-based fluorescence sensor is attributed to its regular higherorder structures, probably a one-handed helical conformation. The resolution ability of Ce-1b as a chiral stationary phase for high-performance liquid chromatography was basically higher than that of the previously reported cellulose tris( phenylcarbamate), revealing that the terthienyl-based pendant provides attractive chiral recognition sites along the helical backbone as well as the fluorescent functionality. † Electronic supplementary information (ESI) available. See

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“…From Deng's group, CPPs simultaneously possessing optical activity and fluorescence properties were prepared by precipitation polymerization of chiral acetylenic monomers containing fluorescent groups. [29] The optical activity of the CPPs aroused not only from the chiral pendant groups but also from the one-handed helical main chain of the polymers. Furthermore, the fluorescent CPPs showed enantioselective fluorescent recognition ability towards alanine and phenylethylamine enantiomers.…”

Section: Polymerization Of Chiral Monomersmentioning

confidence: 99%

“…Besides the applications introduced above, CPPs have also been applied in many other areas, such as selective detection, [80] cell imaging, [81] circularly polarized luminescence (CPL) , [82] and chiral recognition, [6,29,83] Readers can refer to the corresponding references for more details. With the practical applications systematically introduced above, CPPs are expected to be applied to more potential areas such as bioscience and pharmacology to further promote the advancements of chirality-related research.…”

Section: Othersmentioning

confidence: 99%

Preparation and Applications of Chiral Polymeric Particles

Zhang

Huang

Zhao

et al. 2018

Israel Journal of Chemistry

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Chiral polymeric particles (CPPs) have been gathering increasing interest as typical functional polymeric particles in recent decades. This article presents a review on the preparation and applications of CPPs. The methods for preparing CPPs are classified into two major groups: The first one is the direct polymerization of monomers and the other is the post-treatment of preformed polymers. CPPs have been explored as a unique type of chiral materials in various fields like asymmetric catalysis, enantioselective release, enantioselective crystallization, and enantioseparation. This review article is expected to accelerate the progress of scientific research dealing with CPPs and their applications in chirality-related fields.

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Chiral, fluorescent microparticles constructed by optically active helical substituted polyacetylene: preparation and enantioselective recognition ability

Abstract: Novel chiral fluorescent microparticles derived from helical substituted polyacetylene were prepared. The microparticles showed enantioselective recognition ability in both heterogeneous and homogeneous systems.

Cited by 18 publications

References 77 publications

Electrospinning chiral fluorescent nanofibers from helical polyacetylene: preparation and enantioselective recognition ability

Electrospinning chiral fluorescent nanofibers from helical polyacetylene: preparation and enantioselective recognition ability

Chiral fluorescent sensors based on cellulose derivatives bearing terthienyl pendants

Preparation and Applications of Chiral Polymeric Particles

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