Supramolecular relay-control of organocatalysis with a hemithioindigo-based molecular motor
Grill K, Dube H (2020)
Publication Type: Journal article
Publication year: 2020
Journal
Book Volume: 142
Pages Range: 19300-19307
Journal Issue: 45
DOI: 10.1021/jacs.0c09519
Abstract
Integration of individual molecular components such as molecular motors or switches into larger meta-functional systems represents a current challenge at the forefront of molecular machine research. Here we present a modular supramolecular approach to relay the photoinduced geometry changes of a hemithioindigo based molecular motor into catalytic efficiency of a chemical reaction. Using the intrinsic chemical nature of the motor for recognition of different hydrogen-bonding organocatalysts a greater than 10-fold modulation in binding affinity is achieved upon photoisomerization. This change in affinity is then translated effectively into control of catalytic competence of the organocatalysts without direct interference by the motor. As an example the organocatalysed Michael addition reaction between nitrostyrene and 3-methoxy-dimethyl aniline was modulated in situ by visible light irradiation. Thus, dynamic and reversible remote control of catalytic processes by the switching capacity of a hemithioindigo molecular motor is established in a multicomponent chemical system. The high intrinsic modularity of this approach presents further advantages, e.g., for easy tailoring of conditions or facile exchange of catalysts and reactions. These results represent a first stepping stone into integrated chemical networks regulated by molecular machines in a fully dynamic way.
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Germany (DE)How to cite
APA:
Grill, K., & Dube, H. (2020). Supramolecular relay-control of organocatalysis with a hemithioindigo-based molecular motor. Journal of the American Chemical Society, 142(45), 19300-19307. https://doi.org/10.1021/jacs.0c09519
MLA:
Grill, Kerstin, and Henry Dube. "Supramolecular relay-control of organocatalysis with a hemithioindigo-based molecular motor." Journal of the American Chemical Society 142.45 (2020): 19300-19307.
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