A molecular motor from lignocellulose

Thomas Freese, Bálint Fridrich, Stefano Crespi, Anouk S. Lubbe, Katalin Barta*, Ben L. Feringa*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

Lignin is the largest natural source of functionalized aromatics on the planet, therefore exploiting its inherent structural features for the synthesis of aromatic products is a timely and ambitious goal. While the recently developed lignin depolymerization strategies gave rise to well-defined aromatic platform chemicals, the diversification of these structures, especially toward high-end applications is still poorly addressed. Molecular motors and switches have found widespread application in many important areas such as targeted drug delivery systems, responsive coatings for self-healing surfaces, paints and resins or muscles for soft robotics. They typically comprise a functionalized aromatic backbone, yet their synthesis from lignin has not been considered before. In this contribution, we showcase the synthesis of a novel light-driven unidirectional molecular motor from the specific aromatic platform chemical 4-(3-hydroxypropyl)-2,6-dimethoxyphenol (dihydrosynapyl alcohol) that can be directly obtained from lignocellulose via a reductive catalytic fractionation strategy. The synthetic path takes into account the principles of green chemistry and aims to maintain the intrinsic functionality of the lignin-derived platform molecule.

Original languageEnglish
Pages (from-to) 3689–3696
Number of pages8
JournalGreen Chemistry
Volume24
Issue number9
Early online dateApr-2022
DOIs
Publication statusPublished - 2022

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