Issue 14, 2020

Dynamic pH responsivity of triazole-based self-immolative linkers


Gating the release of chemical payloads in response to transient signals is an important feature of ‘smart’ delivery systems. Herein, we report a triazole-based self-immolative linker that can be reversibly paused or slowed and restarted throughout its elimination cascade in response to pH changes in both organic and organic-aqueous solvents. The linker is conveniently prepared using the alkyne–azide cycloaddition reaction, which introduces a 1,4-triazole ring that expresses a pH-sensitive intermediate during its elimination sequence. Using a series of model compounds, we demonstrate that this intermediate can be switched between active and dormant states depending on the presence of acid or base, cleanly gating the release of payload in response to a fluctuating external stimulus.

Graphical abstract: Dynamic pH responsivity of triazole-based self-immolative linkers

Supplementary files

Article information

Article type
Edge Article
29 Jan 2020
28 Feb 2020
First published
03 Mar 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2020,11, 3713-3718

Dynamic pH responsivity of triazole-based self-immolative linkers

D. A. Roberts, B. S. Pilgrim, T. N. Dell and M. M. Stevens, Chem. Sci., 2020, 11, 3713 DOI: 10.1039/D0SC00532K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity