Abstract
Low photostability in aqueous solutions is the main drawback of synthetic photochromic dyes, which limits their switching performance and utility in biology, medicine, and life sciences. Even the most promising photochromes-reversibly photoswitchable diarylethenes (DAEs) with fluorescent "closed" forms-are known to undergo only several tens (typically 20-30) of switching cycles in aqueous solutions. In this work, we introduce water-soluble and highly photostable 1,2-[bis(2-ethyl/2-isobutyl-1-benzothiophene-1,1-dioxide-6-phenyl-3-yl)]perfluorocyclopentenes decorated with four -CONHC(CH2R)3 residues capped with 12 carboxylic acid groups (R = CH2CO2H, O(CH2)2CO2H). Under irradiation with UV (365 nm) and visible light (470 nm), they provide several hundred (for the "rapid" DAEs with isobutyl groups, up to 1000) full switching cycles in aqueous solutions without exclusion of air oxygen (outperforming the photoswitchable and fluorescent protein Dreiklang). The new branching approach based on secondary carboxamides with N-tert-alkyl residues decorated with polar groups may serve as a blueprint for the design of highly fatigue resistant and reversibly photoswitchable fluorescent probes applicable in life sciences as aqueous solutions.
Highlights
Organic photochromic dyes have been applied as molecular switches[1] in photo- and supramolecular chemistry, materials science, optogenetics, and bioimaging
The new branching approach based on secondary carboxamides with N
A challenging problem in the design of fluorescent diarylethenes (DAEs) relates to water solubility and switching performance in aqueous buffers.[6−8,11] We previously reported a series of polycarboxylated DAEs (DAE-n×COOH; Scheme 1, compounds 1a−c) and demonstrated their switching in aqueous solutions and first applications in superresolution microscopy.[6−8] We designed an automated setup and developed a uniform methodology for evaluation of the switching performance of DAEs.[8]
Summary
Organic photochromic dyes have been applied as molecular switches[1] in photo- and supramolecular chemistry, materials science, optogenetics, and bioimaging. (a) Photochromism of Sulfone Derivatives of DAEs with Fluorescent Closed-Ring Isomers Emitting Visible Light,[16,17] (b) Tetra- and Octa-Acids,[6,7] and (c) Long-Chain (6-R1-R2) and Short-Chain (7-R1-R2) DodecaAcids with N-(tert-Alkyl)amido Groups (DAE-12×COOH; This Work) photoswitchable DAEs with unprecedented fatigue resistance in aqueous solutions. These fluorescent molecular switches accommodate hundreds (up to 1000) of switching cycles in purely aqueous solutions without exclusion of air oxygen and under alternating irradiations with UV and visible light. The new synthetic fluorescent switchers can be seriously compared with the reversibly photoswitchable fluorescent proteins (rsFPs) Dreiklang and EGFP2
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