The title compound, C23H22F6O4S2, a photochromic dithienylethene, is a promising material for optical storage and other optoelectrical devices. The molecule adopts a photoactive antiparallel conformation in the crystalline state. The distance between the two reactive C atoms which are involved in potential ring closure is 3.829 (4) A. The dihedral angles between the central cyclopentene ring and the adjacent thiophene rings are 55.38 (7) and 54.81 (9) degrees. The colourless crystals turn magenta when exposed to UV radiation and the process is reversible.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1107/S0108270105025758 | DOI Listing |
Chem Sci
December 2024
National Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University Wuhan 430079 P. R. China
Developing dithienylethene (DTE)-based fluorescence switches triggered by biocompatible visible light has always been a long-term goal in view of their potential in numerous biological scenarios. However, their practical availability is severely limited by the short visible light (generally less than 500 nm) required for photocyclization, their inability to achieve red or near-infrared emission, and their short fluorescence lifetimes. Herein, we present a novel DTE derivative featuring a dimethylamine-functionalized BF-curcuminoid moiety (NBDC) by using an "acceptor synergistic conjugation system" strategy.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560012, India.
Photoswitchable molecules with structural flexibility can exhibit a complex ground state potential energy landscape due to the accessibility of multiple metastable states at merely low energy barriers. However, conventional bulk analytical techniques are limited in their ability to probe these metastable ground states and their relative energies. This is partially due to the difficulty of inducing changes in small molecules in their ground state, as they do not respond to external stimuli, such as mechanical force, unless they are incorporated into larger polymer networks.
View Article and Find Full Text PDFACS Omega
December 2024
Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, Virginia 23529, United States.
Diarylethenes (DAEs) are an important class of photoswitchable compounds that typically undergo reversible photochemical conversions between the open and closed cyclized forms upon treatment with UV light or visible light. In this study, we introduced thioacid functional groups to several photochromic dithienylethene (DTE) derivatives and established a method that can be used to prepare these photoswitchable thioacids. Four thioacid-functionalized diarylethene derivatives were synthesized through the activation of carboxylic acids with -hydroxysuccinimide, followed by reactions with sodium hydrosulfide with yields over 90%.
View Article and Find Full Text PDFSpectrochim Acta A Mol Biomol Spectrosc
March 2025
Luoyang Key Laboratory of Organic Functional Molecules, College of Food and Drug, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934, PR China. Electronic address:
The development of photochromic dithienylethene (DTE) derivatives activated by visible light, particularly those exhibiting aggregation-induced emission (AIE) properties, is highly sought after for applications in photoelectric functional materials and biological systems. In this study, we rationally designed and successfully synthesized a novel cyanostilbene- and nitro-functionalized DTE derivative (6) featuring a reinforced acceptor (A)-DTE-acceptor (A) structural motif. Each of the two cyanostilbene fragments bearing nitrobenzene groups imparts both electron-withdrawing effects and AIE characteristics, thereby ensuring efficient visible light-driven photochromic performance.
View Article and Find Full Text PDFChemistry
December 2024
ISCR (Institut des Sciences Chimiques de Rennes), Univ Rennes, CNRS, UMR 6226, 35000, Rennes, France.
The synthetic methodology for the preparation of photoresponsive dioxazaborocanes-containing oligomers is developed. It relies on the transformation of the (diisopropylamino)boryl group (-BH(NiPr)) into a dioxazaborocane unit in the presence of β-aminodiols and involves a bis-borylated dithienylethene photochromic unit. The photophysical properties of the obtained oligomers are evaluated as well as their processability for the preparation of spin-coated films.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!