Photoswitchable electron-rich phosphines: using light to modulate the electron-donating ability of phosphines

Florenz Buß; Mowpriya Das; Daniel Janssen-Müller; Alexander Sietmann; Ankita Das; Lukas F. B. Wilm; Matthias Freitag; Michael Seidl; Frank Glorius; Fabian Dielmann

doi:10.1039/D3CC04050J

Photoswitchable electron-rich phosphines: using light to modulate the electron-donating ability of phosphines†‡

Florenz Buß,^a Mowpriya Das,^b Daniel Janssen-Müller,^bc Alexander Sietmann,^d Ankita Das,^b Lukas F. B. Wilm,^a Matthias Freitag,^b Michael Seidl,^d Frank Glorius

*^b and Fabian Dielmann

*^ad

Author affiliations

* Corresponding authors

^a Westfälische Wilhelms-Universität Münster, Institut für Anorganische und Analytische Chemie, Corrensstraße 30, Münster 48149, Germany

^b Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstraße 36, Münster 48149, Germany
E-mail: glorius@uni-muenster.de

^c Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, Göttingen 37077, Germany

^d Institute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, Center for Chemistry and Biomedicine, Innrain 80-82, Innsbruck A-6020, Austria
E-mail: fabian.dielmann@uibk.ac.at

Abstract

The synthesis and properties of photoswitchable electron-rich phosphines containing N-heterocyclic imines equipped with a photochromic dithienylethene unit are reported. Heteronuclear NMR spectroscopy and UV/vis studies reveal that the imine substituents undergo reversible electrocyclic ring-closing and ring-opening reactions upon exposure to UV and visible light, respectively. The photoisomerization alters the electron-donating ability of the phosphines by up to ΔTEP = 8 cm⁻¹.

Chemical Communications

Photoswitchable electron-rich phosphines: using light to modulate the electron-donating ability of phosphines†‡

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Photoswitchable electron-rich phosphines: using light to modulate the electron-donating ability of phosphines

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