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349. Fujita T, Iyi N, Klapyta Z (1998) Preparation of azobenzene-mica complex and its
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350. Ueda M, Kim HB, Ichimura K (1994) Photochemical and thermal isomerization of azobenzene
derivatives in sol-gel bulk materials. Chem Mater 6:1771–1775. https://doi.org/10.1021/
cm00046a033
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macp.1978.021791014
352. Nabetani Y, Takamura H, Hayasaka Y, Sasamoto S, Tanamura Y, Shimada T, Masui D,
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353. Koteja A, Szczerba M, Matusik J (2017) Smectites intercalated with azobenzene and
aminoazobenzene: structure changes at nanoscale induced by UV light. J Phys Chem Solids
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354. Irie M, Fukaminato T, Matsuda K, Kobatake S (2014) Photochromism of diarylethene
molecules and crystals: memories, switches, and actuators. Chem Rev 114:12174–12277
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photochromic diarylethene derivatives. Nippon Kagaku Kaishi 112:1138–1140. https://doi.
org/10.1246/nikkashi.1992.1138
356. Irie M, Lifka T, Uchida K, Kobatake S, Shindo Y (1999) Fatigue resistant properties of
photochromic dithienylethenes: by-product formation. Chem Commun:747–748
357. Higashiguchi K, Matsuda K, Kobatake S, Yamada T, Kawai T, Irie M (2000) Fatigue
mechanism of photochromic 1,2-bis(2,5-dimethyl-3-thienyl)perfluorocyclopentene. Bull
Chem Soc Jpn 73:2389–2394. https://doi.org/10.1246/bcsj.73.2389
358. Yokoyama S, Hirose T, Matsuda K (2015) Photoinduced four-state three-step ordering
transformation of photochromic terthiophene at a liquid/solid interface based on two principles: photochromism and polymorphism. Langmuir 31:6404–6414. https://doi.org/10.1021/
acs.langmuir.5b01404
359. Frath D, Sakano T, Imaizumi Y, Yokoyama S, Hirose T, Matsuda K (2015) Diarylethene selfassembled monolayers: cocrystallization and mixing-induced cooperativity highlighted by
scanning tunneling microscopy at the liquid/solid interface. Chem A Eur J 21:11350–11358.
https://doi.org/10.1002/chem.201500804
360. Fukumoto S, Nakashima T, Kawai T (2011) Photon-quantitative reaction of a
dithiazolylarylene in solution. Angew Chem Int Ed 50:1565–1568. https://doi.org/10.1002/
anie.201006844
361. Iijima S, Nakashima T, Kawai T (2016) Stereoselective photoreaction in P-stereogenic
dithiazolylbenzo[b]phosphole chalcogenides. New J Chem 40:10048–10055. https://doi.org/
10.1039/c6nj02446g
314
T. Yamaguchi et al.
dye in the hydrophobic interlayer spaces of organoammonium-fluor-tetrasilisic micas. Clay
Sci 65:57–65. https://doi.org/10.11362/jcssjclayscience1960.10.57
346. Okada T, Nozaki N, Seo J, Kwon JE, Park SY, Hashizume H, Sasaki T, Ogawa M (2017)
Photoinduced structural changes of cationic azo dyes confined in a two dimensional nanospace
by two different mechanisms. RSC Adv 7:8077–8081. https://doi.org/10.1039/C6RA27749G
347. Ohtani O, Itoh T, Monna Y, Sasai R, Shichi T, Yui T, Takagi K (2005) Design of
photofunctional laminated organized thin films: photochromism of ammoniumazobenzene
arenecarboxylates cast on silica glass. Bull Chem Soc Jpn 78:698–702. https://doi.org/10.
1246/bcsj.78.698
348. Umemoto T, Ohtani Y, Tsukamoto T, Shimada T, Takagi S (2014) Pinning effect for
photoisomerization of a dicationic azobenzene derivative by anionic sites of the clay surface.
Chem Commun 50:314–316. https://doi.org/10.1039/c3cc47353h
349. Fujita T, Iyi N, Klapyta Z (1998) Preparation of azobenzene-mica complex and its
photoresponse to ultraviolet irradiation. Mater Res Bull 33:1693–1701
350. Ueda M, Kim HB, Ichimura K (1994) Photochemical and thermal isomerization of azobenzene
derivatives in sol-gel bulk materials. Chem Mater 6:1771–1775. https://doi.org/10.1021/
cm00046a033
351. Eisenbach CD (1978) Effect of polymer matrix on the cis-trans isomerization of azobenzene
residues in bulk polymers. Macromol Chem Phys 179:2489–2506. https://doi.org/10.1002/
macp.1978.021791014
352. Nabetani Y, Takamura H, Hayasaka Y, Sasamoto S, Tanamura Y, Shimada T, Masui D,
Takagi S, Tachibana H, Tong Z, Inoue H (2013) An artificial muscle model unit based on
inorganic nanosheet sliding by photochemical reaction. Nanoscale 5:3182–3193. https://doi.
org/10.1039/c3nr34308a
353. Koteja A, Szczerba M, Matusik J (2017) Smectites intercalated with azobenzene and
aminoazobenzene: structure changes at nanoscale induced by UV light. J Phys Chem Solids
111:294–303. https://doi.org/10.1016/j.jpcs.2017.08.015
354. Irie M, Fukaminato T, Matsuda K, Kobatake S (2014) Photochromism of diarylethene
molecules and crystals: memories, switches, and actuators. Chem Rev 114:12174–12277
355. Taniguchi H, Shinpo A, Okazaki T, Matsui F, Irie M (1992) Photodegradation mechanism of
photochromic diarylethene derivatives. Nippon Kagaku Kaishi 112:1138–1140. https://doi.
org/10.1246/nikkashi.1992.1138
356. Irie M, Lifka T, Uchida K, Kobatake S, Shindo Y (1999) Fatigue resistant properties of
photochromic dithienylethenes: by-product formation. Chem Commun:747–748
357. Higashiguchi K, Matsuda K, Kobatake S, Yamada T, Kawai T, Irie M (2000) Fatigue
mechanism of photochromic 1,2-bis(2,5-dimethyl-3-thienyl)perfluorocyclopentene. Bull
Chem Soc Jpn 73:2389–2394. https://doi.org/10.1246/bcsj.73.2389
358. Yokoyama S, Hirose T, Matsuda K (2015) Photoinduced four-state three-step ordering
transformation of photochromic terthiophene at a liquid/solid interface based on two principles: photochromism and polymorphism. Langmuir 31:6404–6414. https://doi.org/10.1021/
acs.langmuir.5b01404
359. Frath D, Sakano T, Imaizumi Y, Yokoyama S, Hirose T, Matsuda K (2015) Diarylethene selfassembled monolayers: cocrystallization and mixing-induced cooperativity highlighted by
scanning tunneling microscopy at the liquid/solid interface. Chem A Eur J 21:11350–11358.
https://doi.org/10.1002/chem.201500804
360. Fukumoto S, Nakashima T, Kawai T (2011) Photon-quantitative reaction of a
dithiazolylarylene in solution. Angew Chem Int Ed 50:1565–1568. https://doi.org/10.1002/
anie.201006844
361. Iijima S, Nakashima T, Kawai T (2016) Stereoselective photoreaction in P-stereogenic
dithiazolylbenzo[b]phosphole chalcogenides. New J Chem 40:10048–10055. https://doi.org/
10.1039/c6nj02446g
314
T. Yamaguchi et al.