ANALYTICAL CHEMISTRY
·
2020
·
IF 6.785
Shanshan Wu,Qiumin Ye,Datong Wu,Yongxin Tao,Yong Kong
Glycine (Gly), an achiral amino acid, has never been reported for enantioselective recognition owing to the absence of chiral sites. Herein, a facile strategy of chirality transfer is proposed to endow Gly with chirality. Optically active CuO, L-CuO, is first prepared, which can be used for the decoration of Gly through the formation of the Cu(Gly)2 complex. Successful chirality transfer from L-CuO to Gly is confirmed by circular dichroism (CD) spectra. The formation of the Cu(Gly)2 complex is further confirmed by Fourier transform infrared spectra and X-ray photoelectron spectroscopy. Next, the resultant L-CuO-Gly is used for chiral analysis of the isomers of tryptophan (Trp). Because of the higher affinity of L-CuO-Gly toward L-Trp than its isomer, the Trp isomers exhibit significant differences in their oxidation peak currents at the L-CuO-Gly-modified glassy carbon electrode (GCE) (IL-Trp/ID-Trp = 5.24). Finally, the practicability of the developed L-CuO-Gly/GCE is assessed, and the results indicate that it could be a reliable chiral sensor for the quantitative analysis of Trp isomers in nonracemic mixtures.
研究领域:
生物化学
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分析化学
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DOI
PubMed
高影响因子
MACROMOLECULES
·
2018
·
IF 5.914
Huli Yu,Kai Pan,Jianping Deng
Alkynylated carboxymethylcellulose (A-CMC) was used to construct optically active helical polymer microparticles (spherical and spindle-like) through suspension polymerization of achiral acetylic monomer. Taking advantage of the “sergeant and soldiers rule”, the chirality of A-CMC effectively transferred to the resulting helical polymers, thus inducing the latter to form predominantly one-handed screw sense and endowing the microparticles with optical activity. Simply adjusting the stirring speed in suspension polymerizations provided spherical and spindle-like microparticles. The microparticles were assembled by small spheres, under the guidance of oriented A-CMC macromolecular chains depending on stirring rate. The spherical and spindle microparticles demonstrated different enantio-differentiating release process due to their varied shape. A-CMC concurrently plays three roles in the present study: as stabilizing agent and chiral source for fabricating chiral helical polymer particles and as template for adjusting the particles’ shape. The study provides new approaches to utilize biomacromolecules as chiral source for developing novel chiral bioconjugated materials.
研究领域:
材料科学
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高分子化学
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生物材料
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产品关联
DOI
高影响因子
NEW JOURNAL OF CHEMISTRY
·
2021
·Vol. 45
·期 6
·3193-3201
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IF 3.591
Lianglin Zhang,Shuwei Lin,Yi Li,Baozong Li,Yonggang Yang
Four Ala–Ala dipeptides with a semi-perfluoroalkyl chain were synthesized. The intermolecular hydrogen bonding among amide groups and carboxyl groups as well as the hydrophobic association of semi-perfluoroalkyl chains drove the self-assembly of dipeptides. Homochiral dipeptides were able to self-assemble into coiled nanoribbons in a mixed solvent of DMSO/H2O (5/5, v/v), while entangled twisted nanofibers formed for heterochiral ones in a mixed solvent of DMSO/H2O (4/6, v/v). The handedness of self-assemblies and the stacking chirality of phenylene groups were controlled by the chirality of the alanine residue at the C-terminal. The vibration circular dichroism investigation indicated that the helicity of the semi-perfluoroalkyl chain was controlled by the handedness of dipeptide self-assemblies. The X-ray diffraction study showed that homochiral and heterochiral dipeptides underwent distinct molecular packing during the self-assembly. Our results clearly demonstrated that, through supramolecular self-assembly, the chirality transferred from the amino acid building block to the self-assemblies and eventually to the semi-perfluoroalkyl chain.
研究领域:
生物化学
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材料科学
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分子生物学
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产品关联
DOI
高影响因子
DYES AND PIGMENTS
·
2021
·
IF 4.889
Rongqiao Wang,Shibing Chen,Qiaoru Chen,Hongyu Guo,Fafu Yang
abstract Porphyrin with circularly polarized luminescence (CPL) in aggregated state was seldom presented due to the strong aggregation-caused quenching (ACQ) effect at aggregation. This work designed and synthesized a novel porphyrin derivative ( CPL-P ) with good CPL behaviour in aggregated states based on the strong AIE-FRET effect and good chirality transfer of liquid crystalline porphyrin, which was constructed by using porphyrin unit as core with four AIE cyanostilbene groups bearing peripheral chiral alkyl chains. CPL-P exhibited orderly hexagonal columnar mesophase between 62.5 °C and 113.2 °C. It displayed excellent fluorescence emission at 640–760 nm in aggregated states due to the AIE-FRET effect between cyanostilbene unit and porphyrin moiety. Moreover, CPL-P showed the strong circular dichroism and CPL properties in aggregated states based on the effective chiral transfer of the spiral liquid crystalline self-assembly. The |g lum | value for mesophase attained 6.6 × 10 −3 based on the combining effect of AIE-FRET and chiral transfer. This research supplied a new strategy for transferring typical achiral porphyrin with ACQ effect to luminescent molecule with good CPL behaviour in aggregated state.
研究领域:
化学
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材料科学
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DOI
高影响因子
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
·
2020
·Vol. 22
·期 30
·17299-17305
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IF 3.43
Chenyang Zhou,Ya Chu,Linlin Ma,Yingqian Zhong,Chao Wang,Yalan Liu,Haoyue Zhang,Beibei Wang,Xia Feng,Xi Yu,Xiaotao Zhang,Yan Sun,Xiaozeng Li,Guangjiu Zhao
In this work, we introduced halogen-substituted chiral molecules as A-site cations to synthesize a series of novel organic–inorganic hybrid two-dimensional (2D) chiral perovskite materials (R-X-p-mBZA)2PbBr4 (X = H, F, Cl, Br; p: para-position; mBZA = α-methylbenzylamine) for the first time. This halogen-substituted cation strategy collectively solved problems of narrow emission, weak chirality and low photoluminescence quantum yield (PLQY) for the emerged chiral perovskites. Photoluminescence (PL) spectra are significantly broadened due to the additional emission from self-trapped excitons (STEs) besides free excitons (FEs) states modulated by introducing significant disorder to the Pb–Br–Pb angle. The chirality of A-site chiral molecules is transferred and amplified to entire perovskite materials by fixing the chiral molecules at A-site via the interaction of halogen atoms. Furthermore, their PLQYs are improved with the reduction of energy gap and inhibition of the non-radiative transition from STEs to ground state. The halogen-substituted A-site cation strategy can be performed to develop organic–inorganic hybrid chiral perovskites with various optoelectronic applications.
研究领域:
材料科学
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光学
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产品关联
DOI
PubMed
高影响因子
Frontiers of Optoelectronics
·
2024
·Vol. 17
·期 1
·1-7
·
IF 4.1
Li Zha,Li Wancai,Li Dehui,Tang Wei,Liang Huageng,Song Huaibing,Chen Chao,Gao Liang,Tang Jiang
Chiral inorganic semiconductors with high dissymmetric factor are highly desirable, but it is generally difficult to induce chiral structure in inorganic semiconductors because of their structure rigidity and symmetry. In this study, we introduced chiral ZnO film as hard template to transfer chirality to CsPbBr 3 film and PbS quantum dots (QDs) for circularly polarized light (CPL) emission and detection, respectively. The prepared CsPbBr 3 /ZnO thin film exhibited CPL emission at 520 nm and the PbS QDs/ZnO film realized CPL detection at 780 nm, featuring high dissymmetric factor up to around 0.4. The electron transition based mechanism is responsible for chirality transfer. Graphical Abstract
研究领域:
材料科学
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光学
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产品关联
DOI
PubMed
高影响因子
ChemPlusChem
·
2018
·Vol. 83
·期 11
·1038-1043
·
IF 3.205
Song Wang,Hejin Jiang,Li Zhang,Jian Jiang,Minghua Liu
Graphical Supramolecular gels formed from hemin and histidine amphiphiles were tested as artificial enzymes to catalyse the oxidation of the chiral substrate L-DOPA to L-dopachrome. The supramolecular gel made up of left-handed helices enhanced the catalytic activity of hemin effectively, and more interestingly, it exhibited enantioselectivity. Supramolecular co-assembly provides an efficient way to combine structural and functional units through noncovalent interactions and produce materials with enhanced performance. Here, using a chiral amphiphilic histidine derivative (LHC18 or DHC18) as a gelator, we have successfully co-assembled the gelator and hemin through gelation. During the co-assembly, the chiral information of the gelator was transcribed into the assemblies, and thus right- and left-handed helical ribbons from LHC18-Hemin and DHC18-Hemin co-assemblies were obtained, respectively, which were confirmed by CD spectra and SEM observations. These helical ribbons were used as artificial enzymes to catalyse the oxidation reaction of 3,4-dihydroxy-L-phenylalanine (L-DOPA). The catalytic activity of hemin in supramolecular gels can be effectively enhanced over that of free hemin. Moreover, by virtue of induced chirality, the supramolecular gels of LHC18-Hemin and DHC18-Hemin exhibited obvious enantioselective activity. This work provides a way to combine chirality transfer and supramolecular asymmetric catalysis.
研究领域:
生物化学
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材料科学
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产品关联
DOI
PubMed
高影响因子
Journal of Materials Chemistry C
·
2022
·Vol. 10
·期 14
·5598-5607
·
IF 8.067
Tianwen Fan,Xiaohong Chen,Denghui Liu,ShiJian Su,Hongyu Guo,Fafu Yang
The chiral transfer from peripheral chiral groups to the fluorescence achiral core has been confirmed as an effective strategy for preparing CPL liquid crystalline materials. In this work, we introduced a novel strategy for constructing columnar liquid crystals with CPL emission based on a chiral column core with peripheral emitting moieties. Three (1R, 2R)-1,2-cyclohexanediamine-bridged bis-cyanostilbene derivatives with pentyl, octyl or dodecyl chains (CC-5, CC-8 and CC-12) were synthesized in high yields. They possessed excellent aggregation-induced emission in various aggregated states. They displayed good gel properties and CC-8 exhibited an orderly self-assembled fibrous structure due to the cooperation of hydrogen bonds, van der Waals forces and π–π interaction forces. They showed a hexagonal columnar mesophase with chiral units as the core of the column surrounded by the moieties of cyanostilbene with alkyl chains. The CD and CPL investigation suggested that they had good CD and CPL properties for achiral cyanostibene units, suggesting the effective chiral transfer from the chiral column core to the peripheral emitting moieties. The highest CD and CPL properties were observed for CC-8 with octyl chains in the mesophase. This kind of chiral transfer from the core to the periphery was reported for the first time and supplied a new strategy for preparing CPL materials based on achiral dyes.
研究领域:
材料科学
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光学
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DOI
高影响因子
Journal of Materials Chemistry C
·
2020
·Vol. 8
·期 39
·13632-13641
·
IF 7.059
Youde Chen,Peng Lu,Yongjie Yuan,Hailiang Zhang
Circularly polarized luminescent (CPL) materials show great potential applications in asymmetric synthesis, chemical sensors, biological probes, 3D displays and other fields. However, the preparation of high efficiency circularly polarized luminescent materials with a high solid fluorescence quantum yield and a large glum value is still a challenge. This article creatively combines the construction strategy of CPL materials and side-chain chiral liquid crystal polymer materials to engineer a series of new CPL-active side-chain chiral liquid crystal polymers (named PGAC-m, m is the spacer length, m = 4, 6, 10). The chiral poly(L-glutamate) with an α-helical secondary structure is devised as the backbone, and the cyanostilbene with aggregation-induced emission enhancement (AIEE) characteristics is applied as luminescent mesogen pendants, which is covalently linked to the backbone by different spacer lengths. The phase structure and the photophysical properties of PGAC-m were characterized in detail. The experimental results show that PGAC-m can self-assemble to form a lamellar-ordered chiral smectic C (SmC*) phase structure and show typical AIEE characteristics with high solid-state quantum yield. The chirality of polypeptides can be transferred to cyanostilbene, which makes PGAC-m emit circularly polarized light. Meanwhile, the chiral helix structure of PGAC-m can effectively enlarge the glum value, and therefore PGAC-m shows high solid quantum yield and a large glum value. Interestingly, the photophysical properties of PGAC-m can be regulated by changing the spacer length. The solid fluorescence quantum yield of PGAC-m decreases gradually with the increase of spacer length, while the glum value shows the opposite trend. The maximum solid fluorescence quantum yield and the glum value of PGAC-m can be 34.1% and 4.5 × 10−2, respectively.
研究领域:
材料科学
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光学
·
高分子化学
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产品关联
DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
·
2021
·
IF 6.165
Hongyu Guo,Qi Yu,Yuzhi Xiong,Fafu Yang
The first ionic liquid crystals with circularly polarized luminescence were observed based on diphenylacrylonitrile-imidazole salts bearing chiral alkyl chains. Their ordered spiral hexagonal columnar mesophase with long alkyl chains leaded to the effective chiral transfer and chiroptical amplification, resulting in high luminescence dissymmetry factors.
研究领域:
材料科学
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光学
·
分子化学
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DOI
高影响因子
Soft Matter
·
2021
·Vol. 17
·期 40
·9040-9046
·
IF 3.679
Tianwen Fan,Bangyi Zhou,Hongyu Guo,Fafu Yang
In previous studies, the increasing alkyl length of liquid crystalline molecules enhanced the chiral transfer and resulted in better CPL performance. But no work concerned the influence of alkyl lengths on CPL properties for non-liquid crystalline systems. In this research, three R-binaphthol-based cyanostilbene derivatives with various alkyl chains (BC-5, BC-8 and BC-12) were prepared in yields of 60–69%. They did not exhibit liquid crystalline behavior but were seen as soft materials at room temperature. They displayed excellent AIE fluorescence in aggregated states. Chiroptical investigations suggested good CD and CPL properties for their cyanostilbene units, indicating the successful chiral transfer from the binaphthol moieties to cyanostilbene units. Moreover, the values of gabs for CD signals and glum for CPL signals displayed the changing order of BC-5 > BC-8 > BC-12. These results suggested that the shorter alkyl chains for non-liquid crystalline systems led to stronger CPL emission, which was opposite to the results of the liquid crystalline molecules. This work provided a new strategy for the design and synthesis of chiroptical materials with good CPL properties based on non-liquid crystalline molecules.
研究领域:
有机化学
·
材料科学
✓ 已验证
DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
·
2025
·
IF 5.2
Hongyu Guo,Yanling Huang,Liangbin Lin,Shibing Chen,Fafu Yang
A high luminescence asymmetry factor (g lum ) and an excellent luminescence quantum yield in aggregated state are crucial factors for evaluating the application potential of circularly polarized luminescence (CPL) materials, yet achieving both simultaneously remains challenging. In this work, two AIE-active fluorogens based on two conjugated cyano-distyrylbenzenes attaching one or two cholesterol moieties with amide groups as spacers ( BiCDB-1Ch and BiCDB-2Ch ) were designed and synthesized. Both BiCDB-1Ch and BiCDB-2Ch showed the excellent CPL properties in aggregated states based on their hydrogen-bonding columnar liquid crystalline self-assembly. The absolute fluorescence quantum yield of BiCDB-1Ch with stronger D-A structure was 0.43 and the g lum value was as high as 0.30, which was the highest one among the reported columnar CPL liquid crystals. The detailed liquid crystalline self-assembly behaviour and the mechanism of efficient chirality transfer and amplification were elucidated, providing a strategic approach for developing the novel liquid crystalline materials with superior CPL performance.
研究领域:
材料科学
·
光学
·
有机化学
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）