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Hemiphosphoindigos as a platform for chiroptical or water soluble photoswitching

Author

Listed:
  • Fabien Kohl

    (Department of Chemistry and Pharmacy)

  • Theresa Vogl

    (Department of Chemistry and Pharmacy)

  • Frank Hampel

    (Department of Chemistry and Pharmacy)

  • Henry Dube

    (Department of Chemistry and Pharmacy)

Abstract

Photoswitches are important molecular tools to precisely control the behavior of matter by using light irradiation. They have found application in virtually all applied chemical fields from chemical biology to material sciences. However, great challenges remain in advanced property design including tailored chiroptical responses or water solubility. Here, hemiphosphoindigo (HPI) photoswitches are presented as capable phosphorus-based photoswitches and a distinct addition to the established indigoid chromophore family. Phosphinate is embedded in the core indigoid chromophore and the resulting optimized photoswitches display high thermal stabilities, excellent fatigue resistance and high isomer enrichment. A series of planar, twisted and heterocyclic HPIs are investigated to probe design strategies for advantageous photophysical properties. The phosphinate provides a platform for easily accessible, water-soluble photoswitches, especially interesting for biological applications. Its chiral nature further allows light-induced modulation of chiroptical properties. HPIs therefore open up a distinct structural space for photoswitch generation and advanced light-responsive applications.

Suggested Citation

  • Fabien Kohl & Theresa Vogl & Frank Hampel & Henry Dube, 2025. "Hemiphosphoindigos as a platform for chiroptical or water soluble photoswitching," Nature Communications, Nature, vol. 16(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-56942-3
    DOI: 10.1038/s41467-025-56942-3
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    References listed on IDEAS

    as
    1. Maximilian Sacherer & Frank Hampel & Henry Dube, 2023. "Diaryl-hemiindigos as visible light, pH, and heat responsive four-state switches and application in photochromic transparent polymers," Nature Communications, Nature, vol. 14(1), pages 1-12, December.
    2. Manuel Guentner & Monika Schildhauer & Stefan Thumser & Peter Mayer & David Stephenson & Peter J. Mayer & Henry Dube, 2015. "Sunlight-powered kHz rotation of a hemithioindigo-based molecular motor," Nature Communications, Nature, vol. 6(1), pages 1-8, December.
    3. Benjamin Lukas Regen-Pregizer & Ani Ozcelik & Peter Mayer & Frank Hampel & Henry Dube, 2023. "A photochemical method to evidence directional molecular motions," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    4. Aaron Gerwien & Peter Mayer & Henry Dube, 2019. "Green light powered molecular state motor enabling eight-shaped unidirectional rotation," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
    5. Serena Seshadri & Luke F. Gockowski & Jaejun Lee & Miranda Sroda & Matthew E. Helgeson & Javier Read de Alaniz & Megan T. Valentine, 2020. "Self-regulating photochemical Rayleigh-Bénard convection using a highly-absorbing organic photoswitch," Nature Communications, Nature, vol. 11(1), pages 1-8, December.
    6. Susanne Kirchner & Anna-Lena Leistner & Peter Gödtel & Angelika Seliwjorstow & Sven Weber & Johannes Karcher & Martin Nieger & Zbigniew Pianowski, 2022. "Hemipiperazines as peptide-derived molecular photoswitches with low-nanomolar cytotoxicity," Nature Communications, Nature, vol. 13(1), pages 1-14, December.
    7. Sandra Wiedbrauk & Thomas Bartelmann & Stefan Thumser & Peter Mayer & Henry Dube, 2018. "Simultaneous complementary photoswitching of hemithioindigo tweezers for dynamic guest relocalization," Nature Communications, Nature, vol. 9(1), pages 1-9, December.
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