Issue 35, 2024

Side-chain modification of π-stacked helical poly(quinoline-2,3-diylmethylene) via thiol–ene reaction

Abstract

The modification of side-chain substituents is crucial in defining the structure and physical properties of polymers. In this study, we successfully developed a novel method for the versatile modification of side-chain substituents in poly(quinoline-2,3-diylmethylene) (PQM), a polymer characterized by its π-stacked helical structure. A monomer, featuring a reactive olefin moiety in the side chain of o-allenyl arylisocyanide, was synthesized, and a cyclo-copolymerization reaction was conducted using an organopalladium complex as the initiator. This reaction proceeded selectively, preserving the olefin moieties, and resulted in a π-stacked helical PQM with olefin moieties uniformly arranged along the helical axis. A thiol–ene reaction with various thiols enabled the introduction of a broad range of substituents into the PQM while maintaining its helical structure. Importantly, the addition of these substituents significantly enhanced the solubility and solvent stability of PQM. Notably, the incorporation of bulky sugar derivatives sustained the helical structure even in polar solvents such as acetonitrile. Additionally, this method facilitated the synthesis of block, random, and grafted copolymers, as well as grafted polymers with poly-lactides, expanding the array of potential applications. The development of this facile method for side-chain modification opens new possibilities for exploring the physical properties and functional applications of π-stacked PQM.

Graphical abstract: Side-chain modification of π-stacked helical poly(quinoline-2,3-diylmethylene) via thiol–ene reaction

Supplementary files

Article information

Article type
Paper
Submitted
28 May 2024
Accepted
08 Aug 2024
First published
09 Aug 2024

Polym. Chem., 2024,15, 3563-3571

Side-chain modification of π-stacked helical poly(quinoline-2,3-diylmethylene) via thiol–ene reaction

N. Kanbayashi, S. Odagaki and K. Onitsuka, Polym. Chem., 2024, 15, 3563 DOI: 10.1039/D4PY00583J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements