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Issue 11, 2018
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Spironaphthoxazine switchable dyes for biological imaging

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Abstract

Recent developments in super-resolution microscopy have significantly expanded the requirements for switchable dyes, leading to demand for specially designed molecular 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 photochemical quantum yields for ring-opening and ring-closing are approximately 8% and 1%, respectively, in dichloromethane. The ring-opening and ring-closing reactions have been characterized by time-resolved infrared 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). Photochemical 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 commercial fluorescent dyes to create a small-molecule 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.

Graphical abstract: Spironaphthoxazine switchable dyes for biological imaging

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Publication details

The article was received on 10 Jan 2018, accepted on 17 Feb 2018 and first published on 20 Feb 2018


Article type: Edge Article
DOI: 10.1039/C8SC00130H
Citation: Chem. Sci., 2018,9, 3029-3040
  • Open access: Creative Commons BY license
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    Spironaphthoxazine switchable dyes for biological imaging

    Y. Xiong, A. Vargas Jentzsch, Johannes W. M. Osterrieth, E. Sezgin, I. V. Sazanovich, K. Reglinski, S. Galiani, A. W. Parker, C. Eggeling and H. L. Anderson, Chem. Sci., 2018, 9, 3029
    DOI: 10.1039/C8SC00130H

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