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Issue 37, 2020
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On-demand acid-gated fluorescence switch-on in photo-generated nanospheres

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Herein, we introduce a fast, additive-free, ambient temperature photochemical approach – utilising the novel Diels–Alder cycloaddition of a photo-active ortho-methylbenzaldehyde (oMBA) with a terminal alkyne – for preparing functional acid-sensitive profluorescent nano-/microspheres in one step. Not previously reported, the possibility of applying such a reaction in the context of particle synthesis provides new possibilities for particle design, where multi-step reactivity can be gated into distinct steps. First, a photochemically-gated particle formation step yields a material possessing a reactive, spring-loaded intermediate at every cross-linking point. A second, on-demand step to initiate fluorescence generation subsequently imparts the properties of the chemical transformation to the material itself. The synthesised particles are narrow-disperse with an average diameter ranging from 170–380 nm.

Graphical abstract: On-demand acid-gated fluorescence switch-on in photo-generated nanospheres

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Supplementary files

Article information

28 Feb 2020
06 Apr 2020
First published
07 Apr 2020

Chem. Commun., 2020,56, 4986-4989
Article type

On-demand acid-gated fluorescence switch-on in photo-generated nanospheres

J. P. Hooker, F. Feist, L. Delafresnaye, F. Cavalli, L. Barner and C. Barner-Kowollik, Chem. Commun., 2020, 56, 4986
DOI: 10.1039/D0CC01557A

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