A molecular motor from lignocellulose. Issue 9 (13th April 2022)

• Record Type: Journal Article
• Authors: Freese, Thomas; Fridrich, Bálint; Crespi, Stefano; Lubbe, Anouk S.; Barta, Katalin; Feringa, Ben L.
• Is Part Of: Green chemistry. Volume 24:Issue 9(2022)
• Page Start: 3689
• Page End: 3696
• Publication Date: 2022-04-13
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d2gc00291d
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : This work covers the development of a bio-based molecular motor in an overall yield of 10% when accessed through the lignin content of beech sawdust. Its unidirectional, continuous motion at room temperature is key for potential applications. 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.