Solvent Effects on the Actinic Step of Donor-Acceptor Stenhouse Adduct Photoswitching
Authors: Lerch MM., Di Donato M., Laurent AD., Medved M., Iagatti A., Bussotti L., Lapini A., Buma WJ., Foggi P., Szymanski W., Feringa BL
Autors Affiliation: Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, Groningen, 9747 AG, Netherlands; Department of Radiology, University of Groningen, University Medical Center Groningen, Hanzeplein 1, Groningen, 9713 GZ, Netherlands; European Laboratory for Non Linear Spectroscopy (LENS), via N. Carrara 1, Fiorentino, Sesto, 50019, Italy; Istituto Nazionale di Ottica, Largo Fermi 6, Firenze, 50125, Italy; Dipartimento di Chimica, Università di Perugia, via Elce di Sotto 8, Perugia, 06100, Italy; CEISAM, UMR CNRS 6230, BP 92208, 2 Rue de la Houssinière, Nantes, Cedex 3, 44322, France; Regional Centre of Advanced Technologies and Materials, Department of Physical Chemistry, Faculty of Science, Palacký University in Olomouc, 17. listopadu 1192/12, Olomouc, CZ-771 46, Czech Republic; Department of Chemistry, Faculty of Natural Sciences, Matej Bel University, Tajovského 40, Banská Bystrica, SK-97400, Slovakia; Van
Abstract: Donor-acceptor Stenhouse adducts (DASAs) are negative photochromes that switch with visible light and are highly promising for applications ranging from smart materials to biological systems. However, the strong solvent dependence of the photoswitching kinetics limits their application. The nature of the photoswitching mechanism in different solvents is key for addressing the solvatochromism of DASAs, but as yet has remained elusive. Here, we employ spectroscopic analyses and TD-DFT calculations to reveal changing solvatochromic shifts and energies of the species involved in DASA photoswitching. Time-resolved visible pump-probe spectroscopy suggests that the primary photochemical step remains the same, irrespective of the polarity and protic nature of the solvent. Disentangling the different factors determining the solvent-dependence of DASA photoswitching, presented here, is crucial for the rational development of applications in a wide range of different media.
Journal/Review: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume: 57 (27) Pages from: 8063 to: 8068
More Information: The authors gratefully acknowledge financial support from Laserlab-Europe (LENS002289, grant no. 654148), the Ministry of Education, Culture and Science (Gravitation program 024.001.035), The Netherlands Organization for Scientific Research (NWO-CW, Top grant to B.L.F., VIDI grant no. 723.014.001 for W.S.), the European Research Council (Advanced Investigator Grant, no. 227897 to B.L.F.) and the Royal Netherlands Academy of Arts and Sciences Science (KNAW). M.M. acknowledges the Czech Science Foundation (project no. 16-01618S), the Ministry of Education, Youth and Sports of the Czech Republic (grant NPU I, LO1305), the Grant Agency of the Slovak Republic (VEGA project No. 1/0737/17) and CMST COST Action CM1405 MOLIM: MOLecules In Motion. This research used computational resources of 1) the GENCI-CINES/IDRIS, 2) CCIPL (Centre de Calcul Intensif des Pays de Loire), 3) a local Troy cluster, and 4) the HPCC of the Matej Bel University in Banska Bystrica by using the infrastructure acquired in projects ITMS 26230120002 and 26210120002 supported by the Research and Development Operational Programme funded by the ERDF. The Swiss Study Foundation is acknowledged for a fellowship to M.M.L. We would like to thank Prof. Dr. Wesley R. Browne (University of Groningen, The Netherlands) for fruitful discussions.KeyWords: Biological materials; Light; Spectroscopic analysis; Spectroscopy, Donor acceptors; Photoswitches; Pump-probe spectroscopy; Solvatochromic shifts; Solvent dependence; Solvent effects; Td-dft calculations; Visible light, SolventsDOI: 10.1002/anie.201803058Citations: 13data from “WEB OF SCIENCE” (of Thomson Reuters) are update at: 2020-05-31References taken from IsiWeb of Knowledge: (subscribers only)Connecting to view paper tab on IsiWeb: Click hereConnecting to view citations from IsiWeb: Click here