Chiral Triols for Enantiomeric Separation of Anions

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Solution Overview

Problem

Existing chiral anion-binding agents are often achiral or prepared through difficult and non-stereoselective processes, limiting their use in enantiomeric separation of chiral anions.

Innovation Solution

Development of chiral triols with two perfluorinated aliphatic side chains, prepared through a highly stereoselective and efficient process, which exhibit high anion-binding constants and enable enantiomeric separation of chiral anions by selective enantiomeric coordination.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing chiral anion-binding agents are used, then anion binding capability is achieved, but the agents are achiral or prepared through difficult and non-stereoselective processes

Engineering Contradiction:

Improveanion binding capabilityVSAvoidstereoselective preparation

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The invention changes the chemical structure parameters by introducing perfluorinated aliphatic chains (C1-C12) attached to a central carbon with three hydroxyl groups, creating a specific chiral configuration that enables both high anion binding capability and stereoselective preparation through controlled synthesis conditions

Inventive Principle:

Principle #35Parameter changes

2Reliability

If achiral compounds are used for anion binding, then binding capability is achieved, but enantiomeric separation of chiral anions is prevented

Engineering Contradiction:

Improveanion binding capabilityVSAvoidenantiomeric separation capability

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The invention introduces asymmetry by creating a chiral center at the central carbon atom bonded to three hydroxyl groups and a perfluorinated aliphatic chain, making the compound itself chiral and thus capable of enantiomeric separation through selective coordination with chiral anions

Inventive Principle:

Principle #4Asymmetry

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The chiral triols achieve anion-binding constants up to 4400 M^-1 and facilitate enantiomeric separation of chiral anions, demonstrating high selectivity and efficiency in coordinating preferential enantiomers.

Implementation Method 1

the rigidity of the structure imposed by the cyclic nature of the molecule combined with the hydrogen bonding ability of the alcohol groups allows these compounds to efficiently bind anions

Methodology Applied

Scientific EffectHydrogen bonding:

Implementation Method 2

contacting a compound of formula (I) with a mixture comprising a pair of enantiomers of a chiral anion, so as to obtain a complex (C) consisting of said compound of formula (I) and one enantiomer of said pair

Methodology Applied

Scientific EffectEnantiomeric coordination:

Data Source

PatentEP3757085B1Perfluorinated polyols and their use for the enantiomeric separation of chiral anions

Publication Date: 2021.11.10 CENT NAT DE LA RECH SCI (C N R S)

Figure 1~2

AI summary

The invention relates to perfluorinated polyols and their use for enantiomeric separation of chiral anions. It also relates to a process for preparing such perfluorinated polyols, and to a process for the enantiomeric separation of chiral anions.