Synthesis of Core-Modified Third-Generation Light-Driven Molecular Motors
Open Access
- 21 July 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (16), 10670-10680
- https://doi.org/10.1021/acs.joc.0c01235
Abstract
The synthesis and characterization of a series of light-driven third-generation molecular motors featuring various structural modifications at the central aromatic core are presented. We explore a number of substitution patterns, such as 1,2-dimethoxybenzene, naphthyl, 1,2-dichlorobenzene, 1,1':2',1''-terphenyl, 4,4''-dimethoxy-1,1':2',1''-terphenyl, and 1,2-dicarbomethoxybenzene, considered essential for designing future responsive systems. In many cases, the synthetic routes for both synthetic intermediates and motors reported here are modular, allowing for their post-functionalization. The structural modifications introduced in the core of the motors result in improved solubility and a bathochromic shift of the absorption maxima. These features, in combination with a structural design that presents remote functionalization of the stator with respect to the fluorene rotors, make these novel motors particularly promising as light-responsive actuators in covalent and supramolecular materials.Keywords
Funding Information
- Ministerie van Onderwijs, Cultuur en Wetenschap (024.001.035)
- H2020 European Research Council (694345, 793082)
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