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Photocontrollable Release with Coumarin-Based Profragrances.

Ming Liu¹, Jianwei Han¹, Chenxu Yan¹

¹Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China.

ACS Applied Bio Materials

|January 13, 2022

Summary

Scientists developed light-sensitive profragrances for controlled scent release. These coumarin-based compounds enable long-lasting fragrance delivery on surfaces like wallpaper, monitored by fluorescence.

Keywords:

coumarin fluorescence monitoring photocontrollability profragrances wallpaper

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Area of Science:

Organic Chemistry
Materials Science
Fragrance Technology

Background:

Controllable and lasting scent release on surfaces is a key challenge in flavors and fragrances.
Existing fragrance delivery systems often lack precise control over release kinetics and longevity.

Purpose of the Study:

To design and synthesize novel phototriggered coumarin-based profragrances for controlled fragrance release.
To establish a light-sensitive fragrance delivery system with integrated monitoring capabilities.

Main Methods:

Conjugation of volatile carboxylic fragrances with coumarin derivatives via an activatable ester linkage.
Photocleavage of the ester bond upon light exposure to trigger fragrance release.
Fluorescence spectroscopy to monitor the release process and quantify fragrance concentration.

Main Results:

A series of coumarin-based profragrances were successfully synthesized.
Light exposure enabled slow and controllable release of volatile fragrances under ambient conditions.
The coumarin moiety provided fluorescence monitoring of fragrance release with high linearity (R² > 0.95).
Profragrances demonstrated significantly reduced fragrance release compared to free fragrances, indicating controlled delivery.

Conclusions:

Coumarin-based profragrances offer a versatile phototriggered platform for controlled fragrance release.
This system achieves long-lasting scent on surfaces, demonstrated by sustained wallpaper fragrance.
The integrated fluorescence monitoring allows precise control and understanding of the release dynamics.