With or without a co-solvent? highly efficient ultrafast phenanthrenequinone-electron rich alkene (PQ-ERA) photoclick reactions

Author:

Doze Anna M.12ORCID,Fu Youxin1ORCID,Di Donato Mariangela34ORCID,Hilbers Michiel F.5ORCID,Luurtsema Gert2ORCID,Elsinga Philip H.2ORCID,Buma Wybren Jan56ORCID,Szymanski Wiktor178ORCID,Feringa Ben L.1ORCID

Affiliation:

1. Centre for Systems Chemistry, Stratingh Institute for Chemistry, Faculty of Science and Engineering, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands

2. Department of Nuclear Medicine and Molecular Imaging, University of Groningen, University Medical Centre Groningen, Hanzeplein 1, 9713 GZ Groningen, The Netherlands

3. LENS (European Laboratory for Non-Linear Spectroscopy), via N. Carrara 1, 50019 Sesto Fiorentino (FI), Italy

4. ICCOM-CNR, via Madonna del Piano 10, 50019 Sesto Fiorentino (FI), Italy

5. Van ’t Hoff Institute for Molecular Sciences, University of Amsterdam Science Park 904, 1098 XH Amsterdam, The Netherlands

6. Institute for Molecules and Materials, FELIX Laboratory, Radboud University, Toernooiveld 7c, 6525 ED Nijmegen, The Netherlands

7. Department of Radiology, Medical Imaging Center, University of Groningen, University Medical Centre Groningen, Hanzeplein 1, 9713 GZ Groningen, The Netherlands

8. Department of Medicinal Chemistry, Photopharmacology and Imaging, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV, Groningen, The Netherlands

Abstract

The commonly used solubilizing co-solvent DMSO was found to quench the triplet state of PQ in PQ-ERA photoclick reactions. DMSO-free conditions lead to exceptionally high photoreaction quantum yields and rate constants.

Funder

Ministerie van Onderwijs, Cultuur en Wetenschap

Horizon 2020 Framework Programme

Publisher

Royal Society of Chemistry (RSC)

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