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.

Copper(I)-Iodide Clusters as Carriers for Regulating and Visualizing Release of Aroma Molecules

“…In contrast to encapsulation, the chemical approach relies on nonvolatile and odorless precursors named “profragrances”. − In these systems, volatile molecules are tethered to appropriate substrates through labile chemical bonds. In response to external stimuli, including pH, moisture, and light, the fragrance molecules are then released upon the cleavage of covalent bonds or weak interactions. − However, the applicability of the two routes may be limited by their respective disadvantages, such as uncontrolled release in the case of physical encapsulation or delicate pre-design and specialized organic synthesis in the case of chemical conjugation. Furthermore, their synthesis time is longer than desired.…”

Substituent effect on controlled release of fragrant aldehydes from pH-triggered nicotinoylhydrazone-based precursors

“…11,12 The profragrance system consists of fragrances and substrates bonded together, and the perfume molecules are gradually released once triggered by moisture, heat, light, enzymes and so on with the tunable release rate controlled by the intensity of the stimulus. [13][14][15] Recent innovations in the field are dual-controllable, 16 photolysable (under sunlight, 17 especially), 18 non-covalent bondable, 19 and dynamic covalent bondable profragrances, 20,21 while the latter, in contrast to "classical" profragrances, 22,23 are of particular relevance for this work.…”

Light-Responsive Mesoporous Silica Nanoparticles Loaded with Osmanthus Fragrance for Improving Leather Odor

“…In view of the dilemma, exploring a new strategy is of great importance to realize controlled, uniform, and sustained fragrance release on leather. In recent decades, an ambient-responsive profragrance delivery system has been gradually developed due to the controllable and steady release. − However, the profragrance system only controllably released certain fragrances such as alcohol, aldehyde, and ketone, failing to load various kinds of fragrance molecules, which limits improvement of leather odor. Hence, how to realize ambient-responsive release of various fragrances urgently needs to be addressed.…”