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Kim Kuntze1,2, Daisy R S Pooler1, Mariangela Di Donato3,4

  • 1Stratingh Institute for Chemistry, University of Groningen Nijenborgh 4 9746 AG Groningen The Netherlands b.l.feringa@rug.nl stefano.crespi@kemi.uu.se.

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New barbituric acid molecular motors harness light for motion. A unique hydroxy group facilitates rapid isomerization via an intramolecular hydrogen bond, achieving high quantum yields.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Photochemistry

Background:

  • Visible-light-driven molecular motors are crucial for nanoscale applications.
  • Overcrowded alkene-based motors represent a significant advancement in the field.
  • Barbituric acid derivatives offer a novel scaffold for motor design.

Purpose of the Study:

  • To introduce a new class of visible-light-driven molecular motors based on barbituric acid.
  • To elucidate the mechanism of action, focusing on the role of a unique hydroxy group.
  • To investigate the efficiency and operational characteristics of these novel motors.

Main Methods:

  • Femto- and nanosecond transient absorption spectroscopy to probe excited-state dynamics.
  • Molecular dynamics simulations to model conformational changes and interactions.
  • Low-temperature proton nuclear magnetic resonance (¹H NMR) experiments for structural analysis.

Main Results:

  • The barbituric acid motors operate analogously to second-generation overcrowded alkene motors.
  • A tertiary stereogenic center with a hydroxy group was serendipitously introduced.
  • The hydroxy group forms an intramolecular hydrogen bond, driving sub-picosecond excited-state isomerization.

Conclusions:

  • The intramolecular hydrogen bond is key to the motor's rapid isomerization mechanism.
  • Computational studies predict an excited-state "lasso" mechanism.
  • These motors exhibit a high predicted quantum yield for isomerization (68% in gas phase).