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NEW JOURNAL OF CHEMISTRY · 2023 ·Vol. 47 ·期 42 ·19760-19766 · IF 3.3

A fluorescent sensor for rutin hydrate based on a cyanostilbene macrocycle

Bowen Zha,Ling Zheng,Sining Zheng,Liangbin Lin,Hongyu Guo,Fafu Yang

Rutin hydrate has some pharmacological properties and is widely available in human food and household samples. Although many methods based on large-scale instruments have been established for the detection of rutin hydrate, a simple, rapid and in situ measurement strategy was rarely reported up to now. In this work, a fluorescent sensor based on the cyanostilbene macrocycle (BCM) was developed for detecting rutin hydrate with high selectivity and sensitivity. BCM is a bis-cyanostilbene macrocycle with a bridging thiourea chain prepared by “1 + 1” condensation in 75% yield. BCM possessed a good fluorescence emission at 475 nm with an absolute fluorescence quantum yield of 0.26 in DMSO–H2O (5 : 95). It exhibited good selective detection for rutin hydrate among a series of normal ions and biomolecules with a “turn-off” fluorescence response. The binding constant of BCM for rutin hydrate was 2.4 × 104 M−1 and the detection limit attained 1.16 × 10−7 M. The 1 : 1 sensing mechanism was clarified using Job's plot, and 1H NMR and MS binding spectra. The sensing ability of BCM for rutin hydrate was successfully applied in detecting rutin hydrate in a test paper, three fruits and experiments of standard addition recovery with the recoveries of 90–95%, implying the simple, rapid and in situ detecting potential of BCM for rutin hydrate in real samples and the environment.

研究领域: 分析化学 · 药理学 · 食品科学
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Journal of Materials Chemistry C · 2022 ·Vol. 10 ·期 14 ·5598-5607 · IF 8.067

A chiral column core surrounded by peripheral emitting moieties: a novel strategy for constructing columnar liquid crystals with circularly polarized luminescence

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 · 光学
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JOURNAL OF MOLECULAR STRUCTURE · 2024 · IF 4

High contrast stimuli-responsive fluorescence emitters based on carbazole-cyanostilbene derivatives with aggregation induced emission properties

Wenlong Qu,Xiaoling Niu,Haoyu Ma,Yongliang Liu,Zhen Feng,Shengbo Zhu

Due to the aggregation induced emission (AIE) materials exhibiting obvious fluorescent emission changes under the external stimuli of heat, solvent, force and so on, significant efforts have been directed toward developing AIE-active materials with high contrast stimuli-responsive fluorescence behaviors. Herein, three electron-donor(D)-electron-acceptor(A) and D-A-D type organic fluorescence emitters of Cz-DC-tBu, Cz-DC-CN and Cz-DC-OMe were facilely synthesized using carbazole group as D unit and cyano group as A unit. They showed typical AIE features and exhibited remarkable color changes under mechanical force and in different polarity solvents, respectively. The stimuli-responsive mechanism of the compounds were investigated by powder X-ray Diffraction (PXRD) and density functional theory calculations (DFT), which revealed that the mechanofluorochromic behaviors were associated with the molecular packing modes, and the solvatochromic effects were caused by the intramolecular charge-transfer transition (ICT) effect. Significantly, it was found that Cz-DC-tBu showed high contrast stimuli-responsive behaviors through adjusting the substituent groups on the cyanostilbene unit with CN, OMe, and tBu groups, respectively. This study provided a new strategy for the design of AIE-active stimuli-responsive fluorescence emitters, and made them possible using in stress sensors, chemical detection, memory storage, anti-counterfeiting applications.

研究领域: 材料科学 · 有机化学
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Journal of Materials Chemistry C · 2018 ·Vol. 6 ·期 26 ·7119-7127 · IF 5.976

Preparation and properties of side chain liquid crystalline polymers with aggregation-induced emission enhancement characteristics

Yongjie Yuan,Jindi Li,Lifang He,Yiwu Liu,Hailiang Zhang

In this article, novel side chain liquid crystalline polymers (SCLCPs) based on cyanostilbene were synthesized to obtain luminescent liquid crystalline materials. The fluorescent luminescence behavior and liquid crystallinity of SCLCPs were evaluated and characterized by differential scanning calorimetry (DSC), polarized optical microscopy (POM), X-ray diffraction (XRD), ultraviolet spectroscopy (UV) and photoluminescence (PL) measurements. Testing results showed that all polymers exhibited good thermo-stability and stable double-layer smectic A phase below the clearing point temperature. The liquid crystalline properties of polymers were affected by the spacer length. The clearing point temperature (Ti) of SCLCPs decreased with increasing spacer length. All polymers were weakly emissive in good solvent but emitted stronger fluorescence in the aggregation state, showing aggregation-induced emission enhancement (AIEE) behavior. The fluorescent luminescence behavior of polymers was closely linked with chemical structure and the fluorescence quantum yield of polymers in solid phase, which increased with increasing spacer length.

研究领域: 材料科学 · 化学
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