When crown ethers finally click: novel, click-assembled, fluorescent enantiopure pyridino-crown ether-based chemosensors – and an N-2-aryl-1,2,3-triazole containing one

Balázs Szemenyei,Mira Malmosi,Ildikó Móczár,Péter Huszthy,Dávid Pál,László Drahos,Péter Baranyai

doi:10.1039/d1nj04173h

Abstract

Fluorescent chemosensors containing differently connected 1,2,3-triazole units for enantiomeric recognition studies of chiral protonated primary amines and amino acid esters.

Highlights

Enantiomeric differentiation of chiral primary ammonium salts is of great importance,[1,2] because organic molecules with similar structures are often drug molecules
Our interest turned to 1,8-naphthalimides for their advantageous properties for sensing, easy synthesis and derivatization,[33] we prepared pyridino-crown ether (S,S)-3 (Fig. 1) into which a naphthalimide unit was introduced via a click reaction
Synthesis The synthesis of pyridino-crown ether type sensor molecules (S,S)1–(S,S)-4 containing a triazole unit is outlined in Schemes 1–3

Summary

Introduction

Enantiomeric differentiation of chiral primary ammonium salts is of great importance,[1,2] because organic molecules with similar structures are often drug molecules. There have been reported examples, where azides or alkynes bearing already fluorescent moieties were connected to macrocycles by a click reaction to obtain chemosensors having various fluorophores,[29] e.g., 1,8-naphthalimide among others.[31,32] Our interest turned to 1,8-naphthalimides for their advantageous properties for sensing, easy synthesis and derivatization,[33] we prepared pyridino-crown ether (S,S)-3 (Fig. 1) into which a naphthalimide unit was introduced via a click reaction.

Results

Conclusion