Circularly Polarized Luminescence of Aluminum Complexes for Chiral Sensing of Amino Acid and Amino Alcohol

Abstract

Determination of the absolute configuration (AC) of chiral molecules is ak ey issue in many fields related to chirality such as drug development, the asymmetric reaction screening, and the structure determination of natural compounds. Although variousm ethods, such as X-ray crystallography and NMR spectroscopy,a re used to determine the AC, asimple and cheap alternative methodisa lways anticipated. So far,e lectronic circular dichroism (ECD) spectroscopy has been widely used to ascertain the AC and enantiomeric excess (ee)v alues by applying appropriate organic probes. Here, circularly polarizedl uminescence (CPL) spectroscopy was applied to determine the AC and ee values of as eries of amino acid and amino alcohol. The measurements were conductedb ym ixingt he amino acids or amino alcohols with an achiral 1-hydroxy-2-naphthaldehyde.U pon in situ formation of the Schiff base complexes, the system showede mission enhancement and CPL in the presence of Al 3 + ,w hose intensity and sign can be used to assign the chiral senseo ft he amino acids and amino alcohols. Thea uthenticity of the method was furthercompared with the established CD spectroscopy, revealing that CPL spectra of formed Al 3 + complex were effective to determine the AC of chiral species.

Self‐Reporting Activated Ester‐Amine Reaction for Enantioselective Multi‐Channel Visual Detection of Chiral Amines

“…Because of the presence of both helicity and photoluminescence, CPL was expected for the final products, [24] which could also be used as enantioselective CPL detector to determine the configuration and ee value of chiral amines (Figure 5a) [25] . For chiral amines such as 2‐nonanamine, 1‐cyclohexylethylamine, and 1‐phenylethylamine, the CPL signals of the obtained solution had the same sign regardless of the opposite configurations (Figure S46), suggesting that the screw sense of the resultant polymer was controlled by the initial chiral amide pendant in sP‐PFP‐C9* .…”

Synthesis of Substituted 1‐Hydroxy‐2‐Naphthaldehydes by Rhodium‐Catalyzed C−H Bond Activation and Vinylene Transfer of Enaminones with Vinylene Carbonate

“…make them a kind of excited state intramolecular proton transfer (ESIPT) probe [1a–b] . In addition, metal mixed‐ligand chelates based on 1‐hydroxy‐2‐naphthaldehydes often possess optical and magnetic properties [1c–d] . Thus, development of novel and efficient protocols for the synthesis of 1‐hydroxy‐2‐naphthaldehyde derivatives will be valuable for the screening of biological and optoelectronic molecules.…”

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.…”