Solvent Effects on the Actinic Step of Donor-Acceptor Stenhouse Adduct Photoswitching

Year: 2018

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: Univ Groningen, Stratingh Inst Chem, Ctr Syst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands; Univ Groningen, Univ Med Ctr Groningen, Dept Radiol, Hanzepl 1, NL-9713 GZ Groningen, Netherlands; European Lab Non Linear Spect LENS, Via N Carrara 1, I-50019 Sesto Fiorentino, Italy; Ist Nazl Ottica, Largo Fermi 6, I-50125 Florence, Italy; Univ Perugia, Dipartimento Chim, Via Elce Sotto 8, I-06100 Perugia, Italy; CEISAM, UMR CNRS 6230, BP 92208,2 Rue Houssiniere, F-44322 Nantes 3, France; Palacky Univ, Fac Sci, Dept Phys Chem, Reg Ctr Adv Technol & Mat, 17 Listopadu 1192-12, CZ-77146 Olomouc, Czech Republic; Matej Bel Univ, Fac Nat Sci, Dept Chem, Tajovskeho 40, SK-97400 Banska Bystrica, Slovakia; Univ Amsterdam, Vant Hoff Inst Mol Sci, Sci Pk 904, NL-1098 XH Amsterdam, Netherlands.

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, Solvents
DOI: 10.1002/anie.201803058

ImpactFactor: 12.257
Citations: 75
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