Quantitative Chirality and Concentration Sensing of Alcohols, Diols, Hydroxy Acids, Amines and Amino Alcohols using Chlorophosphite Sensors in a Relay Assay

Abstract

Analytical methods that allow simultaneous determination of the concentration and enantiomeric composition of small sample amounts and are also compatible with highthroughput multi-well plate technology have received increasing attention in recent years. We now introduce a new class of broadly useful small-molecule probes and a relay sensing strategy that together accomplish these tasks with five classes of compounds including the challenging group of mono-alcohols-a scope that stands out among previously reported UV, fluorescence, and CD assays. Several chlorophosphite probes and aniline indicators have been evaluated and used for on-thefly CD/UV sensing following a continuous workflow. The wide application range of the readily available sensors is highlighted with almost 30 alcohols, diols, hydroxy acids, amines and amino alcohols, and the accuracy of the stereochemical analysis is showcased with samples covering a wide range of concentrations and enantiomeric ratios.

N-alkylation briefly constructs tunable multifunctional sensor materials: Multianalyte detection and reversible adsorption

“…The multianalyte detection concept, which was first proposed by De Silva's group ( Magri et al., 2006 ; Schmittel and Shu, 2012 ; Chen et al., 2015 ; Magri, 2021 ), has become a hotspot in the field of sensors owing to its advantages of high efficiency, rapidity, simultaneous recognition and in-situ detection ( Xu et al., 2017 ; Park et al., 2018 ; Zhang et al., 2018 ; Chen et al., 2019a ; Zhao et al., 2021 ; Slenders et al., 2021 ; Huang et al., 2021b ; Nakamitsu et al., 2021 ). Multianalyte sensors were originally designed for multiple metal ions ( Magri et al., 2006 ), but these systems have subsequently been developed for multiple bioactive molecules ( Yin et al., 2018 ; Zhang et al, 2020b ; Thanzeel et al., 2020 ), bacteria ( Zheng et al., 2018 ), etc. In some cases, multifunctional sensors based on fluorescent gels ( Zhang et al., 2018 ; Ozay et al., 2020 ) or polymers ( Ozay et al., 2020 ; Liu et al., 2020 ; Huang et al., 2021a ) can simultaneously remove analytes, thus reducing the cost of pollutant treatment in practical applications.…”

Chiroptical Switching and Quantitative Chirality Sensing with (Pseudo)halogenated Quinones

“…In accordance with our chiral amine sensing study, these additional 21 substrates were selected to encompass structures exhibiting asmall aromatic ring as well as some that are devoid of ac hromophore and therefore increasingly challenging.N evertheless,d istinct CD effects were obtained without exception just by fast mixing of the assay components and CD analysis without further delay (see SI). [19,[38][39][40][41][42][43] Scheme 1. Chiroptical redox switching using NaBH 4 and air as external stimuli.…”

Four‐Component Ugi Reaction for Optical Chirality Sensing and Surface Nanoengineering of Chiral Self‐Assemblies

“…In this case, normally relatively weak dissymmetry factor of chiroptical properties such as CD signal will be given at around 10 −4 grade, ascribed to the small dot product between dipole moments [20] . Utilization of condensation reaction, click chemistry, metal‐ligand coordination, substitution reaction and supramolecular host‐guest complexation, chirality could transfer to chromophores with active CD or CPL activities, which have been applied in precise optical chirality determination of amine, acids and hydroxyl compounds [21–31] . The above reactions are normally occurred between two compounds including chiral small molecules and achiral chromophores.…”

“…[20] Utilization of condensation reaction, click chemistry, metal-ligand coordination, substitution reaction and supramolecular host-guest complexation, chirality could transfer to chromophores with active CD or CPL activities, which have been applied in precise optical chirality determination of amine, acids and hydroxyl compounds. [21][22][23][24][25][26][27][28][29][30][31] The above reactions are normally occurred between two compounds including chiral small molecules and achiral chromophores. Exploration of multiple component reaction route to induce the emergence of chiroptical properties and sensing applications is a promising strategy for multiple functional sensing and chiroptical applications.…”