A Helically-twisted Stereodynamic Probe for Chiroptical Sensing of Chiral Amines through Point-to-helical Chirality Transmission.

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2025-01-02 DOI:10.1002/asia.202401376

Aasheesh Srivastava, Akash Kumar Sharma, Arunima Cheran, Jatish Kumar

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Abstract

Chiral amines and amino alcohols form an important category of molecules employed in the designing of new drugs and catalyst. Herein, we present a helically-twisted stereodynamic dialdehyde probe 1 for the determining of absolute configuration, and enantiomeric excess of chiral amine and amino alcohols. Probe 1 is based on the pyridine-2,6-dicarboxamide (PDC) core and undergoes rapid interconversion between the P- and M- conformers. However, upon imine formation with chiral amines, probe 1 gets locked it in a single conformer majorly. This induces a strong CD signal in addition to changes in the UV-vis and fluorescence signals. The CD spectral change allowed for quantitative enantiomeric excess determination of chiral amines. Circular polarized luminescence (CPL) spectra having the glum of 1×10-3 was obtained upon imine formation between probe 1 and diamine 2. Single crystal X-ray diffraction studies (SCXRD) confirmed the twisted conformation in 1@(R)-4 and 1@(S)-4, stabilized by intramolecular hydrogen bonding between bound imine nitrogen and proximate amide group.

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).