Issue 9, 2024

BP23C7: high-yield synthesis and application in constructing [3]rotaxanes and responsive pseudo[2]rotaxanes

Abstract

A biphenyl-23-crown-7 ether (BP23C7) is synthesized in 86% yield from commercially available starting materials. BP23C7 forms pseudo[2]rotaxane with a dibenzylammonium ion (DBA+), exhibiting a good association constant value (ka = 1 × 103 M−1). Subsequently, fluorophoric properties of BP23C7 and anthracene terminated axles are blended to create responsive pseudo[2]rotaxanes. The “turn-on” fluorescence response of BP23C7 due to the addition of fluoride and chloride anions to pseudo[2]rotaxane systems has been investigated. Concomitant fluorescence quenching of the anthracene moiety of corresponding axles due to ion-pair formation has been addressed. Furthermore, two variants of [23]crown ethers, i.e. BP23C7 and o-xylene-23-crown-7 ether (X23C7), are applied for constructing homo[3]rotaxane architectures. A half-axle comprising of DBA+ moiety and a terminal olefin is mixed separately with two [23]crown ethers and subjected to self-metathesis using Grubbs’ first-generation catalyst.

Graphical abstract: BP23C7: high-yield synthesis and application in constructing [3]rotaxanes and responsive pseudo[2]rotaxanes

Supplementary files

Article information

Article type
Paper
Submitted
23 Dec 2023
Accepted
12 Jan 2024
First published
12 Jan 2024

Org. Biomol. Chem., 2024,22, 1871-1884

BP23C7: high-yield synthesis and application in constructing [3]rotaxanes and responsive pseudo[2]rotaxanes

M. Prakashni and S. Dasgupta, Org. Biomol. Chem., 2024, 22, 1871 DOI: 10.1039/D3OB02094K

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