Photocontrollable Release with Coumarin-Based Profragrances.

Abstract

The achievement of controllable and lasting scent on a targeted surface is a long-term goal in the field of flavors and fragrances. Herein, we design a novel series of phototriggered coumarin-based profragrances conjugated with volatile carboxylic fragrances via activatable chemical bridge of ester group, thereby achieving the controllable release of volatile fragrances under ambient conditions. Upon exposure to light, the fragile ester group of profragrances allows the slow release of fragrance molecules, building up a new light-sensitive fragrance delivery system. The incorporated coumarin unit of CM-OH as phototrigger is killing two birds with one stone, that is, precise photocontrollable release of fragrance molecules, and unprecedented fluorescence intensity to monitor the releasing process of fragrance molecules with linear relationship (R2 > 0.95). In comparison, the light-induced releasing amount from profragrances of CM-O-EA, CM-O-PEA, CM-O-PA, and CM-O-CA is much lower than corresponding free fragrances by 33-, 8.5-, 13-, and 983-fold, respectively. As demonstrated, the coumarin-based profragrances provide a phototriggered platform to realize the controllable release of volatile fragrances, resulting in a long-lasting headspace concentration on the targeted surface of wallpaper.