INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
·
2024
·Vol. 25
·期 11
·5606
·
IF 4.9
Rong Wang,Kaiyue Song,Zhaoqin Wei,Yue Sun,Xiaoxia Sun,Yu Hu
The chiral H8-BINOL derivatives R-1and R-2were efficiently synthesized via a Suzuki coupling reaction, and they can be used as novel dialdehyde fluorescent probes for the enantioselective recognition of R/S-2-amino-1-phenylethanol. In addition, R-1is much more effective than R-2. Scanning electron microscope images and X-ray analyses show that R-1can form supramolecular vesicles through the self-assembly effect of the π-π force and strong hydrogen bonding. As determined via analysis, the fluorescence of the probe was significantly enhanced by mixing a small amount of S-2-amino-1-phenylethanol into R-1, with a redshift of 38 nm, whereas no significant fluorescence response was observed in R-2-amino-1-phenylethanol. The enantioselective identification of S-2-amino-1-phenylethanol by the probe R-1was further investigated through nuclear magnetic titration and fluorescence kinetic experiments and DFT calculations. The results showed that this mechanism was not only a simple reactive probe but also realized object recognition through an ICT mechanism. As the intramolecular hydrogen bond activated the carbonyl group on the probe R-1, the carbonyl carbon atom became positively charged. As a strong nucleophile, the amino group of S-2-amino-1-phenylethanol first transferred the amino electrons to a carbonyl carbocation, resulting in a significantly enhanced fluorescence of the probe R-1and a 38 nm redshift. Similarly, S-2-amino-1-phenylethanol alone caused severe damage to the self-assembled vesicle structure of the probe molecule itself due to its spatial structure, which made R-1highly enantioselective towards it.
研究领域:
超分子化学
·
有机化学
·
分析化学
✓ 已验证
DOI
PubMed
高影响因子
RSC Advances
·
2022
·Vol. 12
·期 19
·11967-11973
·
IF 4.036
Yafeng Zhang,Huizhen Wang,Hu Yu,Xiaoxia Sun
Phenylalanine an essential aromatic amino acid for humans and animals, cannot be synthesized by humans and animals on their own. However, it synthesizes important neurotransmitters and hormones in the body and is involved in gluconeogenesis and lipid metabolism. Moreover, the two opposite configurations of phenylalanine have different activities. For example, L-phenylalanine is a biologically active optical isomer involved in crucial biological processes, the lack of which will lead to intellectual disability, while D-phenylalanine only acts as a chiral intermediate. In this research, an H8-BINOL chiral fluorescent sensor modified with 1,2,3-triazole was synthesized in high yield (95%) by nucleophilic substitution and click reaction. The chiral fluorescent sensor showed high enantioselectivity toward phenylalanine. L-Phenylalanine enhanced the fluorescence response of the probe significantly, while D-phenylalanine had no obvious fluorescence response change. The enantioselective fluorescence enhancement ratio [ef = (IL − I0)/(ID − I0), where I0 is the fluorescence of the sensor without amino acids] for the highest fluorescence intensity at 20.0 equivalents of amino acids was 104.48. In this way, the probe could be used to identify and differentiate different configurations of phenylalanine.
研究领域:
生物化学
·
分析化学
✓ 已验证
DOI
高影响因子
DYES AND PIGMENTS
·
2023
·
IF 4.5
Fangxiu Li,Yue Sun,Xiaoxia Sun,Yu Hu,Yanli Wu
Due to the hydrophilicity of furan ring and hydroxyl group, and hydrophobicity of benzene ring and cyclohexyl group, the compounds are easy to form hydrophilic and hydrophobic amphoteric vesicles through self-assembly. The self-assembled vesicles were designed and facilely synthesized using the 2-furanboronic acid and H 8 -BINOL by Suzuki coupling reaction, which could serve as a novel probe with high enantioselectivity for D/L-Phe. In SEM and TEM images, after adding the L-Phe, the vesicle structure of the H 8 -BINOL derivatives changed from spherical to dendritic nanotube structures. On the contrary, after the addition of D-Phe, the spherical vesicle structure changed only slightly, indicating that the material had specific recognition for L-Phe. Moreover, the new fluorescent probes had unique rigid structures and obvious enantioselective recognition for phenylalanine in fluorescence testes. In the methanol solution, after adding the L-Phe, the fluorescence intensity of R - 1 and S - 1 decreased significantly at 368 nm and increased at 306 nm, but D-Phe had no obvious fluorescence effect on the probes, which indicated that the fluorescent probes had a good guiding effect on the recognition of amino acids by chiral compounds.
✓ 已验证
DOI
高影响因子
ACS Applied Materials & Interfaces
·
2024
·
IF 8.3
Rong Wang,Kaiyue Song,Lixue Yang,Yue Sun,Xiaoxia Sun,Yu Hu
R-BTOBD exhibited significant aggregation-induced Emission (AIE) characteristics, including high brightness (αAIE ≈ 40), robust light stability, a substantial Stokes shift (128 nm), and a high signal-to-noise ratio, effectively overcoming aggregation-caused quenching (ACQ). Derived from the axially chiral R-H8–BINOL, R-BTOBD was synthesized via nucleophilic cyclization and exhibited pronounced self-assembly properties. Through robust intra- and intermolecular hydrogen bonding interactions, R-BTOBD formed diverse supramolecular structures, including spherical flower-like aggregates, hollow-core triangular tubules, hexagonal tubules, and irregular white block-like stacks. The specific morphology was influenced by factors such as solvent and pH. For fluorescence applications, R-BTOBD can be employed as an effective visual pH detector through an AIE-enhanced excited-state intramolecular proton transfer (AIE-ESIPT) mechanism. When incorporated into pH paper, it exhibited a bright yellow fluorescence across a wide pH range (pH 1–11), transitioning to an intense bright blue fluorescence under strongly basic conditions (pH 12–14). In chiral applications, R-BTOBD demonstrated potential as a chiral switching agent, leveraging the pronounced changes and inversions in its circular dichroism (CD) signals under varying aggregation states and pH conditions. Additionally, it serves as a specific chiral enantioselective fluorescence probe for l-lysine, demonstrating high efficiency and a low detection limit. Given its exceptional fluorescence and chiral properties, this fluorescent material has significant potential for diverse applications in fluorescence, chirality, and visual inspection.
研究领域:
材料科学
·
分析化学
·
生物化学
✓ 已验证
DOI
PubMed
高影响因子
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