1,2‐Dihydro‐1‐hydroxy‐2,3,1‐benzodiazaborine Bearing an Acridine Moiety as a Circular Dichroism Probe for Determination of Absolute Configuration of Mono‐Alcohols

Abstract

A new chiral probe molecule for mono‐alcohols is developed by using 1,2‐dihydro‐1‐hydroxy‐2,3,1‐benzodiazaborine (DAB) bearing an acridine moiety 1. In the presence of mono‐alcohols, DAB 1 forms borate 2 by boronic ester formation, followed by coordination of the acridine moiety to the boron atom. Borate 2 has a chiral center on the boron atom and works as a stereodynamic circular dichroism (CD) probe molecule for chiral mono‐alcohols based on the π–π interaction between the acridine moiety and the carbon–carbon unsaturated moiety on mono‐alcohols.

Experimental and Computational Study of Aminoacridines as MALDI(−)-MS Matrix Materials for the Analysis of Complex Samples

“…4-AA was synthesized following the procedure from Shimo et al 37 For the preparation of 1-AA, the same synthetic methodology was used with slight modifications: 1-nitroacridine was separated from its 3-nitro isomer with column chromatography (eluent: toluene/ethyl acetate/triethylamine 100:5:1), and the reduction was carried out on 10% Pd/C with hydrazine hydrate as the hydrogen source.…”

Boronic acid based dynamic click chemistry: recent advances and emergent applications

“…Shimo et al 58 utilised the DAB moiety to develop a probe for the determination of the absolute configuration of mono-alcohols. The probe, containing a tri-coordinated boron species ( 11 B NMR: δ = 27 ppm), was obtained by mixing 2-FPBA and acridine hydrazine.…”

“…By applying mass spectrometry, they achieved a detection limit of 0.36 mg L À1 and quantitation limits of 1.17 mg L À1 with high accuracy. Shimo et al 58 utilised the DAB moiety to develop a probe for the determination of the absolute conguration of monoalcohols. The probe, containing a tri-coordinated boron species ( 11 B NMR: d ¼ 27 ppm), was obtained by mixing 2-FPBA and acridine hydrazine.…”

2‐Quinolyl Benzodiazaborine: A Tunable Platform for Aggregation‐Induced Emission Luminogens via Formation of Dimeric Borate Crystals with Acid Additives

“…The mechanism of the borate formation is different from that of our previous DAB system with an acridine moiety. [5] In the previous system, the acridine nitrogen directly coordinated to the boron atom upon the boronic ester formation with alcohols (Scheme 1a). In contrast, the 2-quinoline moiety of DAB 1 worked as a Brønsted base to TFA and the generated CF 3 COO À anion coordinated to the boron atom (Figure 1a).…”

“…[3] We have focused on 1,2-dihydro-1-hydroxy-2,3,1-benzodiazaborine (DAB), a boron-containing heteroaromatic compound that is easily synthesized from 2-formylphenylboronic acid and hydrazine, [4] and recently reported a chiral probe for monoalcohols by utilizing boronic ester formation of DAB bearing an acridine moiety (Scheme 1a). [5] During further investigation into DAB-based sensing systems, we have unexpectedly found that DAB 1 with a 2-quinoline moiety was readily converted to corresponding borates 2 upon addition of carboxylic acids, which exhibited strong AIE effects (Scheme 1b).…”