Enantioselective and Chemoselective Optical Detection of Chiral Organic Compounds without Resorting to Chromatography

Bhushan, Ravi

doi:10.1002/asia.202300825

Cited by 4 publications

(2 citation statements)

References 144 publications

(351 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The development of stereoselective synthetic procedures for amino acid analogs is also intricately tied to the need for reliable and precise methods of chiral analysis [ 30 , 31 , 32 , 33 ].…”

Section: Discussionmentioning

confidence: 99%

A Thiourea Derivative of 2-[(1R)-1-Aminoethyl]phenol as a Chiral Sensor for the Determination of the Absolute Configuration of N-3,5-Dinitrobenzoyl Derivatives of Amino Acids

Aiello,

Recchimurzo,

Balzano

et al. 2024

Molecules

View full text Add to dashboard Cite

In the exploration of chiral solvating agents (CSAs) for nuclear magnetic resonance (NMR) spectroscopy designed for the chiral analysis of amino acid derivatives, notable advancements have been made with thiourea–CSAs. 1-TU, derived from 2-[(1R)-1-aminoethyl]phenol and benzoyl isothiocyanate, is effective in the enantiodifferentiation of N-3,5-dinitrobenzoyl (N-DNB) amino acids. In order to broaden the application of 1-TU for configurational assignment, enantiomerically enriched N-DNB amino acids were analyzed via NMR. A robust correlation was established between the relative position of specific 1H and 13C NMR resonances of the enantiomers in the presence of 1-TU. 1,4-Diazabicyclo[2.2.2]octane (DABCO) was selected for the complete solubilization of amino acid substrates. Notably, the para and ortho protons of the N-DNB moiety displayed higher frequency shifts for the (R)-enantiomers as opposed to the (S)-enantiomers. This trend was consistently observed in the 13C NMR spectra for quaternary carbons bonded to NO2 groups. Conversely, an inverse correlation was noted for quaternary carbon resonances of the carboxyl moiety, amide carbonyl, and methine carbon at the chiral center. This observed trend aligns with the interaction mechanism previously reported for the same chiral auxiliary. The configurational correlation can be effectively exploited under conditions of high dilution or, significantly, under sub-stoichiometric conditions.

show abstract

Section: Discussionmentioning

confidence: 99%

A Thiourea Derivative of 2-[(1R)-1-Aminoethyl]phenol as a Chiral Sensor for the Determination of the Absolute Configuration of N-3,5-Dinitrobenzoyl Derivatives of Amino Acids

Aiello,

Recchimurzo,

Balzano

et al. 2024

Molecules

View full text Add to dashboard Cite

show abstract

“…Thus, several approaches for enantioselective analysis have recently been proposed. As a few examples, detection with the utilization of host–guest-functionalized interfaces [molecularly imprinted or grafted with homochiral metal–organic frameworks (HMOFs)], the creation and application of intrinsically chiral surfaces, and fluorescence- or phosphorescence-based sensors. − …”

Section: Introductionmentioning

confidence: 99%

Homochiral Optical Fibers Coated with Nanoscale Films of Metal–Organic Frameworks and Double-Plasmonic Ag and Au for In Situ Enantioselective Detection

Miliutina,

Shilenko,

Burtsev

et al. 2024

ACS Appl. Nano Mater.

View full text Add to dashboard Cite

Chiral recognition and detection of organic compounds represent an important task in the pharmaceutical, biological, and chemical industries since the difference between organic isomers strictly determines their biological activity and medical impact. Common enantioselective analysis performed with sophisticated equipment requires specially trained staff and a longer period of time. In this work, we propose a functional plasmonic fiber for online enantioselective detection and recognition of small organic molecules–cysteine, tyrosine, and omeprazole. Two nanothick layers of plasmon-active metals (Au and Ag) were deposited on the core(s) of a single optical fiber, giving rise to two plasmon absorption bands, which are well evident in transmitted light. The metal surface(s) was grafted with homochiral metal–organic frameworks (HMOFs), with subnanometer chiral pores, which ensured the enantioselective capture of organic enantiomers from their solution. The capture of organic moieties by grafted HMOF(s) (l- or d-MOF-6) results in their preconcentration near the plasmon-active metals, i.e., in the space of plasmonic “evanescent plasmon wave” excitation. As a result of the local enantiomer capture and corresponding changes in the shrouding refractive index, the wavelength shift of the plasmon absorption band(s) position occurs (for one plasmon absorption band in the case of one enantiomer presence or for both plasmon absorption bands in the case of an enantiomer mixture). Such a design of functional double-plasmon-active optical fiber allows the qualitative and quantitative detection of the enantiomers of small organic molecules. The proposed enantioselective detection approach is simple, fast, and based on low-cost equipment.

show abstract

Classification and Identification of Perfume Scents by an Enantioselective Colorimetric Sensor Array of Chiral Metal‐Organic‐Framework‐Based Fabry‐Pérot Films

Zhan,

Kanj,

Heinke

2024

Chemistry A European J

View full text Add to dashboard Cite

Many odors, like perfumes, are complex mixtures of chiral and achiral molecules where the cost‐efficient (enantio‐)selective sensing represents a major technical challenge. Here, we present a colorimetric sensor array of surface‐mounted metal‐organic‐framework (SURMOF) films in Fabry–Pérot (FP) cavities. The optical properties of the FP‐SURMOF films with different chiral and achiral structures are affected by the (enantio‐)selective adsorption of the analytes in the SURMOF pores, resulting in different responses to the analyte molecules. The read‐out of the sensor array is performed by the digital camera of a common smartphone, where the RGB values are determined. By analyzing the sensor array data with simple machine learning algorithms, the analytes are discriminated. After demonstrating the enantioselective response for a pair of pure chiral odor molecules, we apply the sensor array to detect and discriminate a large number (16) of common commercial perfumes and eau de toilettes. While our untrained human nose is not able to discriminate all perfumes, the presented colorimetric sensor array can classify all perfumes with great classification accuracy. Moreover, the sensor array was used to identify unlabeled samples correctly. We foresee such an FP‐chiral‐SURMOF‐based sensor array as a powerful approach toward inexpensive selective odors sensing applications.

show abstract

Enantioselective and Chemoselective Optical Detection of Chiral Organic Compounds without Resorting to Chromatography

Cited by 4 publications

References 144 publications

A Thiourea Derivative of 2-[(1R)-1-Aminoethyl]phenol as a Chiral Sensor for the Determination of the Absolute Configuration of N-3,5-Dinitrobenzoyl Derivatives of Amino Acids

A Thiourea Derivative of 2-[(1R)-1-Aminoethyl]phenol as a Chiral Sensor for the Determination of the Absolute Configuration of N-3,5-Dinitrobenzoyl Derivatives of Amino Acids

Homochiral Optical Fibers Coated with Nanoscale Films of Metal–Organic Frameworks and Double-Plasmonic Ag and Au for In Situ Enantioselective Detection

Classification and Identification of Perfume Scents by an Enantioselective Colorimetric Sensor Array of Chiral Metal‐Organic‐Framework‐Based Fabry‐Pérot Films

Contact Info

Product

Resources

About