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Two-photon absorption of oxindole-based push–pull molecular motors
Stratingh Institute for Chemistry, University of Groningen, 9747AG Groningen, The Netherlands.
Stratingh Institute for Chemistry, University of Groningen, 9747AG Groningen, The Netherlands.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. Stratingh Institute for Chemistry, University of Groningen, 9747AG Groningen, The Netherlands.ORCID iD: 0000-0002-5895-614X
Stratingh Institute for Chemistry, University of Groningen, 9747AG Groningen, The Netherlands.
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2024 (English)In: Journal of Photochemistry and Photobiology A: Chemistry, ISSN 1010-6030, E-ISSN 1873-2666, Vol. 453, article id 115649Article in journal (Refereed) Published
Abstract [en]

Future applications of light-driven molecular motors in bio-based systems and soft materials require their operation with benign, low-energy light irradiation. Here we report four rotary molecular motors based on oxindole units which can be driven by near-infrared light. By installing an electron-withdrawing CN group on the oxindole lower half, in direct conjugation through the alkene axle to the electron-donating OMe substituent on the upper half, our design establishes a rigid push–pull system which red-shifts the absorption maximum further into the visible region. We also show that the induced nonlinearity to the system increases their two-photon absorption cross section, and the operation of oxindole based molecular motors with 800 nm light for the very first time. The motors prepared in this work show improved performance compared to previous oxindole based motors, e.g. visible light addressability up to 530 nm and 1.5-fold increase in quantum yields in both directions, whilst retaining their desirable qualities of easy synthesis and fast rotation speed.

Place, publisher, year, edition, pages
Elsevier BV , 2024. Vol. 453, article id 115649
Keywords [en]
Molecular motors, Oxindole, Push–pull, Two photon absorption
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-366547DOI: 10.1016/j.jphotochem.2024.115649ISI: 001229505200001Scopus ID: 2-s2.0-85190304261OAI: oai:DiVA.org:kth-366547DiVA, id: diva2:1982599
Note

QC 20250708

Available from: 2025-07-08 Created: 2025-07-08 Last updated: 2025-07-08Bibliographically approved

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Pooler, Daisy R. S.

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