Freese Thomas, Fridrich Bálint, Crespi Stefano, Lubbe Anouk S, Barta Katalin, Feringa Ben L
Stratingh Institute for Chemistry, University of Groningen Nijenborgh 4 9747 AG Groningen The Netherlands
Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz Heinrichstrasse 28/II 8010 Graz Austria
Green Chem. 2022 Apr 9;24(9):3689-3696. doi: 10.1039/d2gc00291d. eCollection 2022 May 10.
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 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.
木质素是地球上功能化芳烃的最大天然来源，因此利用其固有结构特征来合成芳烃产品是一个适时且宏伟的目标。虽然最近开发的木质素解聚策略产生了明确的芳烃平台化学品，但这些结构的多样化，尤其是在高端应用方面，仍然没有得到很好的解决。分子马达和开关已在许多重要领域得到广泛应用，如靶向药物递送系统、用于自修复表面的响应性涂层、油漆和树脂或用于软体机器人的肌肉。它们通常包含一个功能化的芳族主链，但此前尚未考虑过由木质素合成它们。在本论文中，我们展示了一种新型光驱动单向分子马达的合成，该分子马达由特定的芳烃平台化学品4-(3-羟丙基)-2,6-二甲氧基苯酚（二氢芥子醇）合成，该化学品可通过木质纤维素的还原催化分馏策略直接获得。合成路径考虑了绿色化学原理，旨在保持木质素衍生平台分子的固有功能。
