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Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

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Updated: Dec 22, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Chiral Fluorescent Recognition by Naphthalimide.

Xuanming Chen¹, Na Hu¹, Huifeng Wei¹

¹College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, China.

Journal of Fluorescence

|May 6, 2020

Summary

This summary is machine-generated.

This study introduces a novel chiral recognition method using a naphthalimide dye (NA) and cucurbituril (CB[7]) assembly. This fluorescent probe effectively distinguishes between D- and L-enantiomers of phenylalanine and phenylalaninol.

Keywords:

Chiral recognition. NA. CB[7]. Assembly

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores

Published on: August 19, 2013

Area of Science:

Analytical Chemistry
Supramolecular Chemistry
Chemical Sensing

Background:

Chirality is crucial in medicine and biochemistry, as enantiomers exhibit different pharmacological activities, metabolic pathways, and toxicities.
Accurate recognition of chiral molecules is a significant challenge and an active area of chemical research.
Developing sensitive and selective methods for chiral discrimination is essential for pharmaceutical and biochemical applications.

Purpose of the Study:

To develop a new fluorescent method for chiral molecular recognition.
To utilize a naphthalimide dye (NA) and cucurbit[7]uril (CB[7]) assembly as a chiral sensing platform.
To investigate the selective detection of D/L-phenylalanine and D/L-phenylalaninol.

Main Methods:

Formation of a 1:1 assembly between naphthalimide dye (NA) as a guest and cucurbit[7]uril (CB[7]) as a host.
Employing the NA⊂CB[7] assembly as a fluorescent probe.
Utilizing fluorescence titration to monitor the interaction with chiral analytes.

Main Results:

The NA⊂CB[7] assembly exhibited differential fluorescence response to D- and L-enantiomers.
Addition of D-phenylalanine or D-phenylalaninol resulted in partial fluorescence quenching of the assembly.
Addition of L-phenylalanine or L-phenylalaninol caused minimal change in the fluorescence intensity of the assembly.

Conclusions:

A chiral recognition platform based on an achiral NA⊂achiral CB[7] assembly was successfully constructed.
The developed method demonstrates selective recognition of D-enantiomers over L-enantiomers.
This approach offers a promising strategy for the fluorescent detection of chiral molecules.