Xiong, Yaoyao; Vargas Jentzsch, Andreas; Osterrieth, Johannes W. M.; Sezgin, Erdinc; Sazanovich, Igor V.; Reglinski, Katharina; Galiani, Silvia; Parker, Anthony W.; Eggeling, Christian; Anderson, Harry L. published an article in 2018, the title of the article was Spironaphthoxazine switchable dyes for biological imaging.Computed Properties of 98946-18-0 And the article contains the following content:
Recent developments in super-resolution microscopy have significantly expanded the requirements for switchable dyes, leading to demand for specially designed mol. switches. We report the synthesis and characterization of a spironaphthoxazine photochromic switch (a derivative of palatinate purple) displaying high photoconversion (85-95%) under readily accessible 405 nm light, broad absorption in the visible, and excellent fatigue resistance. The indole substituent on this spironaphthoxazine is twisted out of conjugation with the naphthalene unit, yet it is crucial for activation with visible light. The open colored merocyanine form of the spironaphthoxazine reverts to the closed form with a lifetime of 4.7 s in dichloromethane at 20°C; this thermal reversion is even faster in more polar solvents. The photochem. quantum yields for ring-opening and ring-closing are approx. 8% and 1%, resp., in dichloromethane. The ring-opening and ring-closing reactions have been characterized by time-resolved IR and transient absorption spectroscopies. Ring opening occurs rapidly (τ = 2.1 ns) and efficiently (∼90%) from the singlet excited state to form an intermediate (assigned as a cisoid merocyanine), which returns to the closed ground state (τ = 4.5 ns) in competition with relaxation to the transoid open form (τ = 40 ns). Photochem. ring closing is a faster and simpler process: the excited state proceeds to the closed spirooxazine with a time constant of 0.28 ns. This photochromic switch can be used in conjunction with com. fluorescent dyes to create a small-mol. switchable fluorescent dyad that shows high contrast and good fatigue resistance in living cells. These properties make the dyads suitable for application in RESOLFT microscopy. The experimental process involved the reaction of tert-Butyl trichloroacetimidate(cas: 98946-18-0).Computed Properties of 98946-18-0
The Article related to spironaphthoxazine switchable dye biol imaging, Biochemical Methods: Spectral and Related Methods and other aspects.Computed Properties of 98946-18-0
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