A photo-stable fluorescent chiral thiourea probe for enantioselective discrimination of chiral guests

Zhang, Xueyan; Yu, Qiuhan; Chen, Shengxin; Dai, Zhenya

doi:10.1039/c8nj00374b

Cited by 15 publications

(10 citation statements)

References 54 publications

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“…The antagonistic effect, namely the appearance or the enhancement of luminescence upon aggregation, already introduced above, is aggregation-induced emission (AIE). , Typically, non-planar molecules with a π-conjugated core would see their intramolecular motions slowed or stopped upon aggregation, thus preventing a non-radiative energy transfer from the excited state to the ground state to occur via intramolecular rotations or vibrations. For example, Dai and co-workers studied several tetraphenylene (TPE) chiral molecules displaying AIE and having thiourea moieties for chiral guest sensing and recognition. , …”

Section: Chiral Photoactive Precursors and Materialsmentioning

confidence: 99%

“…For example, Dai and co-workers studied several tetraphenylene (TPE) chiral molecules displaying AIE and having thiourea moieties for chiral guest sensing and recognition. 195,196 Along with TPE, fluorescent silole derivatives represent one of the most common motifs for AIE materials. It was proposed that the intramolecular rotation of the phenyl rings surrounding the silole core plays a prevalent part in the non-radiative energy transfer process, and that these rotations are prevented in the packed state.…”

Section: Siloles For Aie-cplmentioning

confidence: 99%

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Main-Group-Based Electro- and Photoactive Chiral Materials

2019

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This Review discusses the structure−property relationships in chiral molecules, macromolecules (polymers), and supramolecules (crystals, liquid crystals, or thin films) containing main-group elements. Chirality is a major property in our world, having a prominent influence on processes in biology, chemistry, and physics. Its impact in optics due to its interaction with electromagnetic waves gave rise to a multitude of effects, such as the Cotton effect and circularly polarized luminescence, making possible applications such as 3D displays and polarized sunglasses. Herein, a particular emphasis will be given to the influence of chirality on the conducting and optical properties of molecules or materials containing frontier heteroelements, particularly boron, silicon, phosphorus, and sulfur. These synergic materials are expected to become game-changers in the field of materials science by bringing new properties into the realm of reality, such as chirality-induced spin-selectivity, circularly polarized luminescence, and electrical magnetochiral anisotropy. This Review should be of interest for chemists and also physicists working in the fields of molecular and supramolecular chemistry, and molecular materials in the broadest sense.

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Section: Chiral Photoactive Precursors and Materialsmentioning

confidence: 99%

Section: Siloles For Aie-cplmentioning

confidence: 99%

Main-Group-Based Electro- and Photoactive Chiral Materials

2019

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“…4,5 Due to the advantageous features in cost, simplicity, sensitivity, real-time analysis and automation, optical techniques have attached substantial interests from researchers in recent years. [6][7][8] On the basic of the structural features and constitutional components, the developed chiral sensing can be divided to metal complex based-and polymer based-chiral probes, organic small molecule based-and nanomaterial based-chiral sensors. [9][10][11] For instance, Noguchi et al 12 designed oligophenylenevinylene-based fluorescent chiral sensor for 1,2cyclohexanedicarboxylic acid enantiomers; Wen et al 13 synthesized a fluorescent molecular probe (1,1′-bi-2-naphthol-based bis(naphthylimine) compound (R)-4) for detecting chiral functional amines.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent and Colorimetric Dual-signal Enantiomers Recognition via Enzyme Catalysis: The Case of Glucose Enantiomers Using Nitrogen-doped Silicon Quantum Dots/Silver Probe Coupled with β-D-Glucose Oxidase

Liu

et al. 2020

ANAL. SCI.

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Chiral enantiomers recognition is important but facing tough challenges in the direct quantitative determination for complex samples. In this work, via chosing nitrogen-doped silicon quantum dots (N-SiQD) as optical nanoprobe and constructing N-SiQD/silver (N-SiQD/Ag NPs) complex, β-D-GOx as model enzyme and glucose enantiomers as analytes, a fluorescent and colorimetric dualsignal chiral sensing strategy was proposed herein for chiral recognition based on specific enzymecatalyzed reaction. N-SiQD can exhibit intense fluorescence, while it can be quenched by Ag NPs owing to the formation of N-SiQD/Ag NPs. In the presence of glucose isomer, D-glucose is catalytically hydrolyzed by β-D-GOx to form H 2 O 2 owing to the specific enzyme catalyzed reaction between D-glucose and β-D-GOx, and H 2 O 2 can etch Ag NPs from the N-SiQD/Ag NPs probe to change the solution color from brown to colorless and restore the N-SiQD fluorescence; while these phenomena cannot be caused by L-glucose, a dual-signal sensing method was thus constructed for recognizing glucose enantiomers. It is believed that the chiral enantiomers recognition strategy via

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“…The sensing based on fluorescence is attractive due to the selectivity, high sensitivity and quick response time of fluorescence spectroscopy [3]. Great efforts have been made on the design, synthesis, and use of chiral fluorescent chemosensors [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. The first use of photophysical techniques for elucidation of chiral recognition by crown ethers was reported in 1980 [20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Complexation Studies of Optically Active Aza- and Diazacrown Ethers Containing a Pyrene Fluorophore Unit

Pál

Gede

Móczár

et al. 2019

Period. Polytech. Chem. Eng.

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Novel enantiopure azacrown [(R,R)-1 and (S,S)-1] and diazacrown [(R,R)-2–(R,R)-4 and (S,S)-2–(S,S)-4] ethers containing a pyrene fluorophore unit and two phenyl groups at their chiral centers were obtained in multistep syntheses. The action of these chemosensors is based on the photoinduced electron transfer (PET) process, thus they show fluorescence enhancement in the presence of protonated primary amines and amino acid esters. Their recognition abilities toward the enantiomers of 1-phenylethylamine hydrogen perchlorate (PEA), 1-(1-naphthyl) ethylamine hydrogen perchlorate (NEA), phenylglycine methyl ester hydrogen perchlorate (PGME), and phenylalanine methyl ester hydrogen perchlorate (PAME) were examined in acetonitrile using fluorescence spectroscopy.

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A photo-stable fluorescent chiral thiourea probe for enantioselective discrimination of chiral guests

Abstract: Herein, a chiral thiourea Schiff base derived from (1R,2R)-1,2-cyclohexanediamine and tetraphenylethylene (TPE) was applied as a highly effective chiral sensor for the enantioselective discrimination of various acids and aminesviaion-pair and hydrogen-bond interaction.

Cited by 15 publications

References 54 publications

Main-Group-Based Electro- and Photoactive Chiral Materials

Main-Group-Based Electro- and Photoactive Chiral Materials

Fluorescent and Colorimetric Dual-signal Enantiomers Recognition via Enzyme Catalysis: The Case of Glucose Enantiomers Using Nitrogen-doped Silicon Quantum Dots/Silver Probe Coupled with β-D-Glucose Oxidase

Synthesis and Complexation Studies of Optically Active Aza- and Diazacrown Ethers Containing a Pyrene Fluorophore Unit

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