Optical Chirality Sensing with a Stereodynamic Aluminum Biphenolate Probe

The Journal of Organic Chemistry
Zeus A de Los SantosChristian Wolf

Abstract

The determination of the enantiopurity and the concentration of chiral compounds by chiroptical sensing with molecular probes is increasingly attractive for high-throughput screening applications including streamlined asymmetric reaction development. In this study, we use stereodynamic aluminum biphenolate complexes for quantitative ee and concentration analysis of amino alcohols and α-hydroxy acids. An important feature of the tropos biphenolate ligand used is the presence of a phenylacetylene antenna for optimal chirality recognition and CD/UV responses at high wavelengths. The complexation-driven chirality amplification yields strong CD signals, which allows quantitative chiroptical sensing with good accuracy. We show that aluminate biphenolate sensors can exhibit linear and nonlinear correlations between the induced CD signals and the enantiomeric composition or concentration of the chiral substrate.

References

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Citations

Jul 9, 2020·Chemical Communications : Chem Comm·Sara SheykhiPavel Anzenbacher
Sep 3, 2020·Advanced Materials·Xiaosheng YanYun-Bao Jiang
Mar 16, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ankur GogoiGuan-Yu Zhuo
Jul 25, 2020·The Journal of Organic Chemistry·Samantha L PilicerChristian Wolf
Feb 25, 2020·Langmuir : the ACS Journal of Surfaces and Colloids·Minggao QinChuanliang Feng
Oct 1, 2019·Journal of the American Chemical Society·F Yushra ThanzeelChristian Wolf

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