Chapter 33
Turn-on Mode Photoswitchable
Fluorescent Diarylethenes
for Super-Resolution Fluorescence
Microscopy
Masakazu Morimoto and Masahiro Irie
Abstract Sulfone derivatives of 1,2-bis(2-alkyl-6-aryl-1-benzothiophen-3yl)perfluorocyclopentene have been developed as a new type of turn-on mode photoswitchable fluorescent molecules for super-resolution fluorescence microscopy.
Upon irradiation with ultraviolet (UV) light, the open-ring isomers undergo cyclization reactions to produce the closed-ring isomers, which emit brilliant fluorescence
with high quantum yields ( f ~ 0.9). Upon irradiation with visible light, the
closed-ring isomers revert back to the initial open-ring isomers and the fluorescence
vanishes. The cycloreversion quantum yields of the fluorescent diarylethenes were
tuned by appropriate chemical modifications to fulfill the requirements for the
different types of super-resolution imaging techniques. A turn-on mode fluorescent
diarylethene that shows solvatochromism of fluorescence in the closed-ring form
is potentially applicable to multicolor super-resolution imaging of microscopic
environmental polarity. Unprecedented reversible photoswitching of fluorescent
diarylethene molecules upon irradiation with single-wavelength visible light was
found and has been successfully applied to super-resolution fluorescence imaging.
Keywords Diarylethene · Fluorescence · Photochromism · Photoswitch ·
Super-resolution fluorescence microscopy
33.1 Introduction
Fluorescent molecules with photoswitching ability have been attracting much attention because of their potential applications to optical memory media as well as superresolution fluorescence microscopy [1–5]. Photoswitchable fluorescent molecules
can be constructed by integrating both photochromic and fluorescent chromophores
M. Morimoto (B) · M. Irie
Department of Chemistry and Research Center for Smart Molecules, Rikkyo University, 3-34-1
Nishi-Ikebukuro, Toshima-ku, Tokyo 171-8501, Japan
e-mail: m-morimoto@rikkyo.ac.jp
M. Irie
e-mail: iriem@rikkyo.ac.jp
© Springer Nature Singapore Pte Ltd. 2020
H. Miyasaka et al. (eds.), Photosynergetic Responses in Molecules
and Molecular Aggregates, https://doi.org/10.1007/978-981-15-5451-3_33
563
Turn-on Mode Photoswitchable
Fluorescent Diarylethenes
for Super-Resolution Fluorescence
Microscopy
Masakazu Morimoto and Masahiro Irie
Abstract Sulfone derivatives of 1,2-bis(2-alkyl-6-aryl-1-benzothiophen-3yl)perfluorocyclopentene have been developed as a new type of turn-on mode photoswitchable fluorescent molecules for super-resolution fluorescence microscopy.
Upon irradiation with ultraviolet (UV) light, the open-ring isomers undergo cyclization reactions to produce the closed-ring isomers, which emit brilliant fluorescence
with high quantum yields ( f ~ 0.9). Upon irradiation with visible light, the
closed-ring isomers revert back to the initial open-ring isomers and the fluorescence
vanishes. The cycloreversion quantum yields of the fluorescent diarylethenes were
tuned by appropriate chemical modifications to fulfill the requirements for the
different types of super-resolution imaging techniques. A turn-on mode fluorescent
diarylethene that shows solvatochromism of fluorescence in the closed-ring form
is potentially applicable to multicolor super-resolution imaging of microscopic
environmental polarity. Unprecedented reversible photoswitching of fluorescent
diarylethene molecules upon irradiation with single-wavelength visible light was
found and has been successfully applied to super-resolution fluorescence imaging.
Keywords Diarylethene · Fluorescence · Photochromism · Photoswitch ·
Super-resolution fluorescence microscopy
33.1 Introduction
Fluorescent molecules with photoswitching ability have been attracting much attention because of their potential applications to optical memory media as well as superresolution fluorescence microscopy [1–5]. Photoswitchable fluorescent molecules
can be constructed by integrating both photochromic and fluorescent chromophores
M. Morimoto (B) · M. Irie
Department of Chemistry and Research Center for Smart Molecules, Rikkyo University, 3-34-1
Nishi-Ikebukuro, Toshima-ku, Tokyo 171-8501, Japan
e-mail: m-morimoto@rikkyo.ac.jp
M. Irie
e-mail: iriem@rikkyo.ac.jp
© Springer Nature Singapore Pte Ltd. 2020
H. Miyasaka et al. (eds.), Photosynergetic Responses in Molecules
and Molecular Aggregates, https://doi.org/10.1007/978-981-15-5451-3_33
563