Controlling pH-Sensitive Chemical Reactions Pathways with Light - a Tale of Two Photobases: an Arrhenius and a Brønsted

• Published in: Chemistry : a European journal p. e202303767
• Main Authors: Yucknovsky, Anna, Amdursky, Nadav
• Format: Journal Article
• Language: English
• Published: Germany 11-12-2023
• Subjects: Photobases; 6-Methoxyquinoline; Alizarin Red S; Dynamic networks; Malachite green carbinol base
• ISSN: 1521-3765

Light-gated chemical reactions allow spatial and temporal control of chemical processes. Here, we suggest a new system for controlling pH-sensitive processes with light using two photobases of Arrhenius and Brønsted types. Only after light excitation do Arrhenius photobases undergo hydroxide ion dissociation, while Brønsted photobases capture a proton. However, none can be used alone to reversibly control pH due to the limitations arising from excessively fast or overly slow photoreaction timescales. We show here that combining the two types of photobases allows light-triggered and reversible pH control. We show an application of this method in directing the pH-dependent reaction pathways of the organic dye Alizarin Red S simply by switching between different wavelengths of light, i.e., irradiating each photobase separately. The concept of a light-controlled system shown here of a sophisticated interplay between two photobases can be integrated into various smart functional and dynamic systems.