Issue 4, 2023

Topochemical polymerization in phenylalanine anchored chiral diacetylenes for chiroptical properties and tunable thermo-, halo-, solvatochromism

Abstract

Chiral polymers always have the edge over their achiral analogues owing to the effective utilization of asymmetry to mimic nature in multiple ways. Chirality in tandem with conjugation in polymers creates an excellent platform for optoelectronic properties, leading to futuristic applications based on chiral photonics. Herein, we design two symmetric bis-functionalised phenylalanine tethered chiral diacetylene (DA) monomers that exhibit efficient topochemical polymerization into conjugated ene–yne polydiacetylene (PDA) with an intense red colour. The efficacy of the photopolymerization can be modulated by altering the peripheral functional groups. Interestingly, the individual enantiomers and their mixture show comparable photopolymerization owing to co-assembly. However, the chiroptical properties of the mixtures can be tweaked by the enantiomeric excess complying with the majority rule principle. Finally, the individual chiral PDA exhibits visible changes in optoelectronic and chiroptical properties under external perturbation e.g. temperature, volatile organic solvent and pH, that are investigated using UV-visible and circular dichroism spectroscopy. Such topochemical polymerization assisted by ordered self-assembly in peptide-tethered diacetylene provides convenient access to smart, responsive, chiral optoelectronic materials.

Graphical abstract: Topochemical polymerization in phenylalanine anchored chiral diacetylenes for chiroptical properties and tunable thermo-, halo-, solvatochromism

Supplementary files

Article information

Article type
Paper
Submitted
21 Nov 2022
Accepted
16 Dec 2022
First published
19 Dec 2022

New J. Chem., 2023,47, 1657-1665

Topochemical polymerization in phenylalanine anchored chiral diacetylenes for chiroptical properties and tunable thermo-, halo-, solvatochromism

A. Maulik, C. Miglani, N. A. Mavlankar, J. P. Joseph, V. C. Chandran and A. Pal, New J. Chem., 2023, 47, 1657 DOI: 10.1039/D2NJ05708E

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