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RESEARCH ARTICLE (Open Access)
Contents Vol 75(11)

Tuning the photoreactivity of photocycloaddition by halochromism†

Vinh X. Truong A B * and Christopher Barner-Kowollik https://orcid.org/0000-0002-6745-0570 A B C *
+ Author Affiliations
- Author Affiliations

A Centre for Materials Science, Queensland University of Technology (QUT), 2 George Street, Brisbane, Qld 4000, Australia.

B School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George Street, Brisbane, Qld 4000, Australia.

C Institute of Nanotechnology, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.

* Correspondence to: vx.truong@qut.edu.au, christopher.barnerkowollik@qut.edu.au

Handling Editor: Curt Wentrup

Australian Journal of Chemistry 75(11) 899-905 https://doi.org/10.1071/CH22103
Submitted: 12 May 2022  Accepted: 16 June 2022   Published: 25 July 2022

© 2022 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution 4.0 International License (CC BY)

Abstract

Harnessing the power of light for chemical transformation is a long-standing goal in organic synthesis, materials fabrication and engineering. Amongst all photochemical reactions, [2 + 2] photocycloadditions are inarguably the most important and most frequently used. These photoreactions have green characteristics by enabling new bond formation in a single step procedure under light irradiation, without the need for heat or chemical catalysis. More recently, substantial progress has been made in red-shifting the activation wavelength of photocycloadditions in response to research trends moving towards green and sustainable processes, and advanced applications in biological environments. In the past 5 years, our team has further expanded the toolbox of photocycloaddition reactions that can be triggered by visible light. In our exploration of photochemical reactivity, we found that reactivity is often red-shifted compared to the substrate’s absorption spectrum. Our efforts have resulted in red-shifted photochemical reactions, providing some of the lowest energy – and catalyst-free – photo-activated [2 + 2] cycloadditions (up to 550 nm). More recently, we introduced an additional level of control over such finely wavelength gated reactions by altering the pH of the reaction environment, thus exploiting halochromic effects to enhance or impede the photoreactivity of red-shifted [2 + 2] photocycloaddition reactions. In this account, we discuss the current state of halochromically regulated photochemical reactions and their potential in soft matter materials on selected examples.

Keywords: halochromism, hydrogels, photocrosslinking, photocycloaddition, regioselectivity, single chain nanoparticle, visible light, wavelength-orthogonal.


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