33 Turn-on Mode Photoswitchable Fluorescent Diarylethenes …
579
39. Yang Z, Cao J, He Y, Yang JH, Kim T, Peng X, Kim JS (2014) Macro-/micro-environmentsensitive chemosensing and biological imaging. Chem Soc Rev 43:4563–4601
40. Klymchenko AS (2017) Solvatochromic and fluorogenic dyes as environment-sensitive probes:
design and biological applications. Acc Chem Res 50:366–375
41. Moon S, Yan R, Kenny SJ, Shyu Y, Xiang L, Li W, Xu K (2017) Spectrally resolved, functional super-resolution microscopy reveals nanoscale compositional heterogeneity in live-cell
membranes. J Am Chem Soc 139:10944–10947
42. Morimoto M, Takagi Y, Hioki K, Nagasaka T, Sotome H, Ito S, Miyasaka H, Irie M (2018) A
turn-on mode fluorescent diarylethene: solvatochromism of fluorescence. Dyes Pigm 153:144–
149
43. Mataga N, Kaifu Y, Koizumi K (1955) The solvent effect on fluorescence spectrum, change of
solute-solvent interaction during the lifetime of excited solute molecule. Bull Chem Soc Jpn
28:690–691
44. Mataga N, Kaifu Y, Koizumi K (1956) Solvent effects upon fluorescence spectra and the
dipolemoments of excited molecules. Bull Chem Soc Jpn 29:465–470
45. Lippert E (1957) Spektroskopische Bestimmung des Dipolmomentes aromatischer
Verbindungen im ersten angeregten Singulettzustand. Z Electrochem 61:962–975
46. Sumi T, Kaburagi T, Morimoto M, Une K, Sotome H, Ito S, Miyasaka H, Irie M (2015)
Fluorescent photochromic diarylethene that turns on with visible light. Org Lett 17:4802–4805
47. Fukaminato T, Hirose T, Doi T, Hazama M, Matsuda K, Irie M (2014) Molecular design strategy
toward diarylethenes that photoswitch with visible light. J Am Chem Soc 136:17145–17154
48. Fredrich S, Göstl R, Herder M, Grubert L, Hecht S (2016) Switching diarylethenes reliably in
both directions with visible light. Angew Chem Int Ed 55:1208–1212
49. Zhang Z, Wang W, Jin P, Xue J, Sun L, Huang J, Zhang J, Tian H (2019) A building-block
design for enhanced visible-light switching of diarylethenes. Nat Commun 10:4232
50. Kashihara R, Morimoto M, Ito S, Miyasaka H, Irie M (2017) Fluorescence photoswitching of
a diarylethene by irradiation with single-wavelength visible light. J Am Chem Soc 139:16498–
16501
51. Wondrazek F, Seilmeier A, Kaiser W (1984) Ultrafast intramolecular redistribution and intermolecular relaxation of vibrational energy in large molecules. Chem Phys Lett 104:121–128
52. Kinoshita S, Nishi N, Saitoh A, Kushida T (1987) Urbach tail of organic dyes in solution. J
Phys Soc Jpn 56:4162–4175
53. Mizuno K, Matsui A, Sloan GJ (1984) Intermediate exciton-phonon coupling in tetracene. J
Phys Soc Jpn 53:2799–2806
54. Urbach F (1953) The long-wavelength edge of photographic sensitivity and of the electronic
absorption of solids. Phys Rev 92:1324
55. Birks JB (1970) Photophysics of aromatic molecules. Wiley, London
56. Arai Y, Ito S, Fujita H, Yoneda Y, Kaji T, Takei S, Kashihara R, Morimoto M, Irie M,
Miyasaka H (2017) One-colour control of activation, excitation and deactivation of a fluorescent
diarylethene derivative in super-resolution microscopy. Chem Commun 53:4066–4069
57. Roubinet B, Weber M, Shojaei H, Bates M, Bossi ML, Belov VN, Irie M, Hell SW (2017)
Fluorescent photoswitchable diarylethenes for biolabeling and single-molecule localization
microscopies with optical superresolution. J Am Chem Soc 139:6611–6620
58. Roubinet B, Bossi ML, Alt P, Leutenegger M, Shojaei H, Schnorrenberg S, Nizamov S, Irie M,
Belov VN, Hell SW (2016) Carboxylated photoswitchable diarylethenes for biolabeling and
super-resolution RESOLFT microscopy. Angew Chem Int Ed 55:15429–15433
59. Uno K, Bossi ML, Konen T, Belov VN, Irie M, Hell SW (2019) Asymmetric diarylethenes
with oxidized 2-alkylbenzothiophen-3-yl units: chemistry, fluorescence, and photoswitching.
Adv Optical Mater 7:1801746
60. Uno K, Bossi ML, Irie M, Belov VN, Hell SW (2019) Reversibly photoswitchable fluorescent diarylethenes resistant against photobleaching in aqueous solutions. J Am Chem Soc
141:16471–16478
61. Um SH, Kim HJ, Kim D, Kwon JE, Lee JW, Hwang D, Kim SK, Park SY (2018) Highly
fluorescent and water soluble turn-on type diarylethene for super-resolution bioimaging over
a broad pH range. Dyes Pigm 158:36–41
579
39. Yang Z, Cao J, He Y, Yang JH, Kim T, Peng X, Kim JS (2014) Macro-/micro-environmentsensitive chemosensing and biological imaging. Chem Soc Rev 43:4563–4601
40. Klymchenko AS (2017) Solvatochromic and fluorogenic dyes as environment-sensitive probes:
design and biological applications. Acc Chem Res 50:366–375
41. Moon S, Yan R, Kenny SJ, Shyu Y, Xiang L, Li W, Xu K (2017) Spectrally resolved, functional super-resolution microscopy reveals nanoscale compositional heterogeneity in live-cell
membranes. J Am Chem Soc 139:10944–10947
42. Morimoto M, Takagi Y, Hioki K, Nagasaka T, Sotome H, Ito S, Miyasaka H, Irie M (2018) A
turn-on mode fluorescent diarylethene: solvatochromism of fluorescence. Dyes Pigm 153:144–
149
43. Mataga N, Kaifu Y, Koizumi K (1955) The solvent effect on fluorescence spectrum, change of
solute-solvent interaction during the lifetime of excited solute molecule. Bull Chem Soc Jpn
28:690–691
44. Mataga N, Kaifu Y, Koizumi K (1956) Solvent effects upon fluorescence spectra and the
dipolemoments of excited molecules. Bull Chem Soc Jpn 29:465–470
45. Lippert E (1957) Spektroskopische Bestimmung des Dipolmomentes aromatischer
Verbindungen im ersten angeregten Singulettzustand. Z Electrochem 61:962–975
46. Sumi T, Kaburagi T, Morimoto M, Une K, Sotome H, Ito S, Miyasaka H, Irie M (2015)
Fluorescent photochromic diarylethene that turns on with visible light. Org Lett 17:4802–4805
47. Fukaminato T, Hirose T, Doi T, Hazama M, Matsuda K, Irie M (2014) Molecular design strategy
toward diarylethenes that photoswitch with visible light. J Am Chem Soc 136:17145–17154
48. Fredrich S, Göstl R, Herder M, Grubert L, Hecht S (2016) Switching diarylethenes reliably in
both directions with visible light. Angew Chem Int Ed 55:1208–1212
49. Zhang Z, Wang W, Jin P, Xue J, Sun L, Huang J, Zhang J, Tian H (2019) A building-block
design for enhanced visible-light switching of diarylethenes. Nat Commun 10:4232
50. Kashihara R, Morimoto M, Ito S, Miyasaka H, Irie M (2017) Fluorescence photoswitching of
a diarylethene by irradiation with single-wavelength visible light. J Am Chem Soc 139:16498–
16501
51. Wondrazek F, Seilmeier A, Kaiser W (1984) Ultrafast intramolecular redistribution and intermolecular relaxation of vibrational energy in large molecules. Chem Phys Lett 104:121–128
52. Kinoshita S, Nishi N, Saitoh A, Kushida T (1987) Urbach tail of organic dyes in solution. J
Phys Soc Jpn 56:4162–4175
53. Mizuno K, Matsui A, Sloan GJ (1984) Intermediate exciton-phonon coupling in tetracene. J
Phys Soc Jpn 53:2799–2806
54. Urbach F (1953) The long-wavelength edge of photographic sensitivity and of the electronic
absorption of solids. Phys Rev 92:1324
55. Birks JB (1970) Photophysics of aromatic molecules. Wiley, London
56. Arai Y, Ito S, Fujita H, Yoneda Y, Kaji T, Takei S, Kashihara R, Morimoto M, Irie M,
Miyasaka H (2017) One-colour control of activation, excitation and deactivation of a fluorescent
diarylethene derivative in super-resolution microscopy. Chem Commun 53:4066–4069
57. Roubinet B, Weber M, Shojaei H, Bates M, Bossi ML, Belov VN, Irie M, Hell SW (2017)
Fluorescent photoswitchable diarylethenes for biolabeling and single-molecule localization
microscopies with optical superresolution. J Am Chem Soc 139:6611–6620
58. Roubinet B, Bossi ML, Alt P, Leutenegger M, Shojaei H, Schnorrenberg S, Nizamov S, Irie M,
Belov VN, Hell SW (2016) Carboxylated photoswitchable diarylethenes for biolabeling and
super-resolution RESOLFT microscopy. Angew Chem Int Ed 55:15429–15433
59. Uno K, Bossi ML, Konen T, Belov VN, Irie M, Hell SW (2019) Asymmetric diarylethenes
with oxidized 2-alkylbenzothiophen-3-yl units: chemistry, fluorescence, and photoswitching.
Adv Optical Mater 7:1801746
60. Uno K, Bossi ML, Irie M, Belov VN, Hell SW (2019) Reversibly photoswitchable fluorescent diarylethenes resistant against photobleaching in aqueous solutions. J Am Chem Soc
141:16471–16478
61. Um SH, Kim HJ, Kim D, Kwon JE, Lee JW, Hwang D, Kim SK, Park SY (2018) Highly
fluorescent and water soluble turn-on type diarylethene for super-resolution bioimaging over
a broad pH range. Dyes Pigm 158:36–41