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Abstract
Light is an exceptional external stimulus for establishing precise control over the properties and functions of chemical and biological systems, which is enabled through the use of molecular photoswitches. Ideal photoswitches are operated with visible light only, show large separation of absorption bands and are functional in various solvents including water, posing an unmet challenge. Here we show a class of fully-visible-light-operated molecular photoswitches, Iminothioindoxyls (ITIs) that meet these requirements. ITIs show a band separation of over 100 nm, isomerize on picosecond time scale and thermally relax on millisecond time scale. Using a combination of advanced spectroscopic and computational techniques, we provide the rationale for the switching behavior of ITIs and the influence of structural modifications and environment, including aqueous solution, on their photochemical properties. This research paves the way for the development of improved photo-controlled systems for a wide variety of applications that require fast responsive functions.
The design of photoswitches which operate in the visible light regime, show a large separation of absorption bands and are functional in various solvents is challenging. Here the authors report Iminothioindoxyls as visible-light operated photoswitches with a band separation of 100 nm.
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1 University Medical Center Groningen, University of Groningen, Department of Radiology, Medical Imaging Center, Groningen, The Netherlands; University of Groningen, Faculty of Science and Engineering, Centre for Systems Chemistry, Stratingh Institute for Chemistry, Groningen, The Netherlands (GRID:grid.4830.f) (ISNI:0000 0004 0407 1981)
2 Palacký University in Olomouc, Faculty of Science, Regional Centre of Advanced Technologies and Materials, Olomouc, Czech Republic (GRID:grid.10979.36) (ISNI:0000 0001 1245 3953); Matej Bel University, Faculty of Natural Sciences, Department of Chemistry, Banská Bystrica, Slovak Republic (GRID:grid.24377.35) (ISNI:0000 0001 2359 0697)
3 University of Nantes, CEISAM UMR CNRS 6230, Nantes, France (GRID:grid.4817.a)
4 European Laboratory for Non Linear Spectroscopy (LENS) via N. Carrara 1, Sesto Fiorentino, Italy (GRID:grid.4817.a); INO, Istituto Nazionale di Ottica, Firenze, Italy (GRID:grid.425378.f) (ISNI:0000 0001 2097 1574)
5 INO, Istituto Nazionale di Ottica, Firenze, Italy (GRID:grid.425378.f) (ISNI:0000 0001 2097 1574); University of Amsterdam, Van’t Hoff Institute for Molecular Sciences, Amsterdam, The Netherlands (GRID:grid.7177.6) (ISNI:0000000084992262)
6 University of Groningen, Faculty of Science and Engineering, Centre for Systems Chemistry, Stratingh Institute for Chemistry, Groningen, The Netherlands (GRID:grid.4830.f) (ISNI:0000 0004 0407 1981)
7 Radboud University, Institute for Molecules and Materials, FELIX Laboratory, Nijmegen, The Netherlands (GRID:grid.5590.9) (ISNI:0000000122931605)
8 Radboud University, Institute for Molecules and Materials, FELIX Laboratory, Nijmegen, The Netherlands (GRID:grid.5590.9) (ISNI:0000000122931605); University of Florence, Department of Chemistry ‘Ugo Shiff’, Sesto Fiorentino (FI), Italy (GRID:grid.8404.8) (ISNI:0000 0004 1757 2304)
9 University Medical Center Groningen, University of Groningen, Department of Radiology, Medical Imaging Center, Groningen, The Netherlands (GRID:grid.8404.8); University of Groningen, Faculty of Science and Engineering, Centre for Systems Chemistry, Stratingh Institute for Chemistry, Groningen, The Netherlands (GRID:grid.4830.f) (ISNI:0000 0004 0407 1981)