[structure: see text] Bisbinaphthyl-based macrocycles are found to carry out highly enantioselective fluorescent recognition of alpha-hydroxycarboxylic acids. It is observed that within a certain concentration range, one enantiomer of the chiral acids can increase the fluorescence intensity of the macrocycles by 2-3-fold, while the other enantiomer scarcely enhances the fluorescence. Such unusually high enantioselective responses make these macrocycles very attractive as fluorescent sensors in determining the enantiomeric composition of alpha-hydroxycarboxylic acids.
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http://dx.doi.org/10.1021/ol026565c | DOI Listing |
Chemistry
January 2025
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, Freiburg im Breisgau, 79104, Germany.
Reliable radical precursors are crucial for photocatalytic processes. In particular, heteroatom-stabilized radicals have attracted considerable research interest in photocatalysis. Among them, α-amino radicals have received the most attention, while the research on α-hydroxy radicals is much less developed.
View Article and Find Full Text PDFPLoS One
April 2024
Institute of Chemical Industry of Forest Products, CAF Nanjing, Nanjing, China.
To enhance the yield of the one-step synthesis of terpinyl acetate from α-pinene and acetic acid, this study evaluated α-hydroxycarboxylic acid (HCA)-boric acid composite catalysts based on orthogonal experimental design. The most important factor affecting the terpinyl acetate content in the product was the HCA content. The catalytic performance of the composite catalyst was related to the pKa1 of HCA.
View Article and Find Full Text PDFMolecules
December 2023
Guangxi Key Laboratory of Superior Timber Trees Resource Cultivation, Guangxi Forestry Research Institute, Nanning 530002, China.
The complexation of boric acid (BA) with various α-hydroxycarboxylic acids (HCAs) was examined by analyzing the change in the optical rotation after the addition of BA to aqueous HCA solutions, and the catalytic properties of the complexes were examined by catalyzing the esterification of the HCAs. The absolute values of the optical rotation of the HCAs increased with increasing BA-to-HCA molar ratio, and the rate of change of the optical rotation gradually decreased as the BA-to-HCA molar ratio increased, reaching a minimum value at a molar ratio of approximately three. As a catalyst, BA could catalyze the acetylation of hydroxyl groups in addition to the esterification of HCAs.
View Article and Find Full Text PDFInt J Mol Sci
July 2023
Laboratory of Inorganic Chemistry and Advanced Materials, School of Chemical Engineering, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
The prospect of developing soluble and bioavailable Ti(IV) complex forms with physiological substrates, capable of influencing (patho)physiological aberrations, emerges as a challenge in the case of metabolism-related pathologies (e.g., diabetes mellitus 1 and 2).
View Article and Find Full Text PDFMolecules
June 2023
Guangxi Key Laboratory of Superior Timber Trees Resource Cultivation, Guangxi Forestry Research Institute, Nanning 530002, China.
To investigate the synergistic catalytic effects of boric acid and α-hydroxycarboxylic acids (HCAs), we analyzed and measured the effects of the complexation reactions between boric acid and HCAs on the ionization equilibrium of the HCAs. Eight HCAs, glycolic acid, D-(-)-lactic acid, (R)-(-)-mandelic acid, D-gluconic acid, L-(-)-malic acid, L-(+)-tartaric acid, D-(-)-tartaric acid, and citric acid, were selected to measure the pH changes in aqueous HCA solutions after adding boric acid. The results showed that the pH values of the aqueous HCA solutions gradually decreased with an increase in the boric acid molar ratio, and the acidity coefficients when boric acid formed double-ligand complexes with HCAs were smaller than those of the single-ligand complexes.
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