Controllable fragrance release mediated by spontaneous hydrogen bonding with poss–thiourea derivatives

Abstract

The purpose of achieving the long-lasting fragrance perception leads to nanocarrier-based profragrances in perfume applications. Herein, we report a family of novel profragrance systems based on polyhedral oligomeric silsesquioxane (POSS) derivatized thioureas (POSS thioureas) that enable linkage of volatile carbonyl fragrances with the spontaneous formation of fragile hydrogen bonds. This profragrance platform addresses the dilemma of the volatile nature of aroma-materials on the one hand, and the desired long-lasting effects on the other. Their releasing performance as profragrances is investigated by headspace solid-phase microextraction (SPME) in combination with gas chromatography (GC) analysis under water as the external humidity stimulus, indicating that the fragrance concentration released from the POSS–thiourea-based profragrance is up to four times higher than the neat reference of the corresponding perfume aldehydes. Furthermore, deposition of the novel profragrance system onto wallpaper results in excellent retentive capacity for volatile aldehydes. Given the low essential toxicity, the POSS–thiourea system has been demonstrated as a suitable profragrance for practical application to perfume delivery.