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Synthesis of Core-Modified Third-Generation Light-Driven Molecular Motors.


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.

SUBMITTER: Berrocal JA 

PROVIDER: S-EPMC7445741 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Synthesis of Core-Modified Third-Generation Light-Driven Molecular Motors.

Berrocal José Augusto JA   Pfeifer Lukas L   Heijnen Dorus D   Feringa Ben L BL  

The Journal of organic chemistry 20200730 16


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 in  ...[more]

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