Self-assembled nanovesicles based on chiral bis-H<sub>8</sub>-BINOL for Fe<sup>3+</sup> recognition and secondary recognition of <scp>l</scp>-cysteine by 1 + 1 complex

Tao, Jisheng; Wang, Huizhen; Sun, Yue; Sun, Xiaoxia; Hu, Yu

doi:10.1039/d3ra07654g

Cited by 8 publications

(1 citation statement)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Overall, the unique combination of structural features of the H 8 -BINOL derivative allows for spontaneous self-assembly into vesicles, which exhibits important implications for various applications [ 28 , 29 ]. Previously, our group began preliminary studies on the self-assembled structure of H 8 -BINOL and developed novel probes based on the existing studies [ 30 , 31 , 32 ].…”

Section: Introductionmentioning

confidence: 99%

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

Wang,

Song,

Wei

et al. 2024

IJMS

Self Cite

View full text Add to dashboard Cite

The chiral H8-BINOL derivatives R-1 and R-2 were 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-1 is much more effective than R-2. Scanning electron microscope images and X-ray analyses show that R-1 can 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-1 was 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-1 and 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-1 highly enantioselective towards it.

show abstract

Section: Introductionmentioning

confidence: 99%

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

Wang,

Song,

Wei

et al. 2024

IJMS

Self Cite

View full text Add to dashboard Cite

show abstract

Design, Synthesis and Application of 1,4‐disubstituted 1,2,3‐triazole Based Chemosensors: A Promising Avenue

Malik,

Yadav,

Bhushan

2024

The Chemical Record

View full text Add to dashboard Cite

The 1,2,3‐triazole‐based chemosensors, synthesized through Cu(I)‐catalyzed azide‐alkyne cycloaddition via ‘click chemistry’, offer a straightforward yet highly effective method for detecting metal cations and anions with remarkable accuracy, selectivity and sensitivity, making them invaluable across various fields such as chemistry, pharmacology, environmental science and biology. The selective recognition of these ions is crucial due to their significant roles in biological and physiological processes, where even slight concentration variations can have major consequences. The article reviews literature from 2017 to 2024, highlighting advancements in the synthesis of 1,2,3‐triazole‐based ligands and their application (along with sensing mechanism) for detection of various ions causing health and environmental hazards. The detection aspects have been discussed sequentially for the transition‐, inner transition‐, and the metals from the s or p block of the periodic table.

show abstract

Recent advances in photoresponsive-based triazole sensors and their applications in biomaterials

Rajasekar,

Narendran,

Mary

et al. 2024

Results in Chemistry

View full text Add to dashboard Cite

Self-assembled nanovesicles based on chiral bis-H₈-BINOL for Fe³⁺ recognition and secondary recognition of l-cysteine by 1 + 1 complex

Abstract: A novel fluorescent “off” sensor, R-β-d-1, was obtained in high yield (91.2%) by using octahydronaphthol as a backbone, introducing an alkyne group at the 2-position, and linking azido-glucose via a click reaction.

Cited by 8 publications

References 41 publications

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

Design, Synthesis and Application of 1,4‐disubstituted 1,2,3‐triazole Based Chemosensors: A Promising Avenue

Recent advances in photoresponsive-based triazole sensors and their applications in biomaterials

Contact Info

Product

Resources

About

Self-assembled nanovesicles based on chiral bis-H8-BINOL for Fe3+ recognition and secondary recognition of l-cysteine by 1 + 1 complex

Abstract: A novel fluorescent “off” sensor, R-β-d-1, was obtained in high yield (91.2%) by using octahydronaphthol as a backbone, introducing an alkyne group at the 2-position, and linking azido-glucose via a click reaction.

Cited by 8 publications

References 41 publications

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

Design, Synthesis and Application of 1,4‐disubstituted 1,2,3‐triazole Based Chemosensors: A Promising Avenue

Recent advances in photoresponsive-based triazole sensors and their applications in biomaterials

Contact Info

Product

Resources

About

Self-assembled nanovesicles based on chiral bis-H₈-BINOL for Fe³⁺ recognition and secondary recognition of l-cysteine by 1 + 1 complex