Abstract
Chirality plays a key role in the physiological system, because molecular functionalities may drastically alter due to a change in chirality. We report herein a unique color indicator with a static helicity memory, which exhibits visible color changes in response to the chirality of chiral amines. A difference of less than 2% in the enantiomeric excess (ee) values causes a change in the absorption that is visible to the naked eyes. This was further quantified by digital photography by converting to RGB values. This system relies on the change in the tunable helical pitch of the π-conjugated polymer backbone in specific solvents and allows rapid on-site monitoring of chirality of nonracemic amines, including drugs, and the simultaneous quantitative determination of their ee values.
Highlights
Chirality is an important aspect in living systems
As part of our ongoing program to develop h-poly1-H–based advanced chiral materials for separating enantiomers [29], we serendipitously found that M-h-poly-1-Hs modified with (S)- and (R)-1-phenylethylamine (S- and R-2a), namely, M-h-poly1-S2a and M-h-poly-1-R2a, respectively, showed completely different colors in specific solvents
The carboxy groups of M-h-poly-1-H were modified with S- and R-2a via amide linkage using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as a condensing reagent, thereby quantitatively producing diastereomeric helices M-h-poly-1-S2a and M-hpoly-1-R2a, respectively
Summary
Chirality is an important aspect in living systems. For instance, a pair of enantiomers often exhibits totally different physiological activities depending on the homochirality of the biological molecule.
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