34 Crystallization Control of the Photoresponsible Diarylethene …
591
When 1o converted to 1c completely, crystals were not formed. 1o underlayer is
necessary for 1c alignment. In this study, the Al plasmonic chip promoted conversion
rate from 1o to 1c. By the comparison of the conversion rate between on the grating
pattern and on the flat metal, high conversion rate more than 60% is found to be
important condition for crystal growth. Therefore, crystal growth can be controlled
by the conversion to 1c which was promoted by the plasmonic field. At conversion
more than 60%, 1c molecules near the film surface and film edge can align on the
1o underlayer platform and gradually grow to crystals.
Acknowledgements T. K and K. T. thank Toyo Gosei for providing the photocurable resin, and
thank Ms. Eri Nakamura for helping our experiment. The present work was supported by JSPS
KAKENHI Grant Number JP15H01100 and JP26107012, Grant-in-Aid for Scientific Research on
Innovative Areas “Photosynergetics.”
References
1. Irie M, Mohri M (1988) Thermally irreversible photochromic systems—reversible photocyclization of diarylethene derivatives. J Org Chem 53:803–808
2. Irie M, Fukaminato T, Matsuda K, Kobatake S (2014) Photochromism of diarylethene
molecules and crystals: memories, switches and actuators. Chem Rev 114:12174–12277
3. Tian H, Yang SJ (2004) Recent progresses on diarylethene based photochromic switches. Chem
Soc Rev 33:85–97
4. Berkovic G, Krongauz V, Weiss V (2000) Spiropyrans and spirooxazines for memories and
switches. Chem Rev 100:1741–1753
5. Minkin VI (2004) Photo-, thermo-, solvato-, and electrochromic spiroheterocyclic compounds.
Chem Rev 104:2751–2776
6. Tamai N, Miyasaka H (2000) Ultrafast dynamics of photochromic systems. Chem Rev
100:1875–1890
7. Natansohn A, Rochon P (2002) Photoinduced motions in azo-containing polymers. Chem Rev
102:4139–4175
8. Bandara HMD, Burdette SC (2012) Photoisomerization in different classes of azobenzene.
Chem Soc Rev 41:1809–1825
9. Priimagi A, Barrett CJ, Shishido A (2014) Recent twists in photoactuation and photoalignment
control. J Mater Chem C 2:7155–7162
10. Hatano S, Abe J (2008) Activation parameters for the recombination reaction of intramolecular
radical pairs generated from the radical diffusion-inhibited HABI Derivative. J Phys Chem A
112:6098–6103
11. Fukaminato T, Sasaki T, Kawai T, Tamai N, Irie M (2004) Digital photoswitching of fluorescence based on the photochromism of diarylethene derivatives at a single-molecule level. J Am
Chem Soc 126:14843–14849
12. Matsuda K, Irie M (2001) Photochromism of diarylethenes with two nitronyl nitroxides:
photoswitching of an intramolecular magnetic interaction. Chem Eur J 7:3466–3473
13. Moriyama Y, Matsuda K, Tanifuji N, Irie S, Irie M (2005) Electrochemical cyclization/cycloreversion reactions of diarylethenes. Org Lett 7:3315–3318
14. Gilat SL, Kawai SH, Lehn JM (1993) Light-triggered electrical and optical switching devices.
J Chem Soc Chem Commun 18:1439–1442
15. Irie M, Kobatake S, Horichi M (2001) Reversible surface morphology changes of a
photochromic diarylethene single crystal by photoirradiation. Science 291:1769–1772
591
When 1o converted to 1c completely, crystals were not formed. 1o underlayer is
necessary for 1c alignment. In this study, the Al plasmonic chip promoted conversion
rate from 1o to 1c. By the comparison of the conversion rate between on the grating
pattern and on the flat metal, high conversion rate more than 60% is found to be
important condition for crystal growth. Therefore, crystal growth can be controlled
by the conversion to 1c which was promoted by the plasmonic field. At conversion
more than 60%, 1c molecules near the film surface and film edge can align on the
1o underlayer platform and gradually grow to crystals.
Acknowledgements T. K and K. T. thank Toyo Gosei for providing the photocurable resin, and
thank Ms. Eri Nakamura for helping our experiment. The present work was supported by JSPS
KAKENHI Grant Number JP15H01100 and JP26107012, Grant-in-Aid for Scientific Research on
Innovative Areas “Photosynergetics.”
References
1. Irie M, Mohri M (1988) Thermally irreversible photochromic systems—reversible photocyclization of diarylethene derivatives. J Org Chem 53:803–808
2. Irie M, Fukaminato T, Matsuda K, Kobatake S (2014) Photochromism of diarylethene
molecules and crystals: memories, switches and actuators. Chem Rev 114:12174–12277
3. Tian H, Yang SJ (2004) Recent progresses on diarylethene based photochromic switches. Chem
Soc Rev 33:85–97
4. Berkovic G, Krongauz V, Weiss V (2000) Spiropyrans and spirooxazines for memories and
switches. Chem Rev 100:1741–1753
5. Minkin VI (2004) Photo-, thermo-, solvato-, and electrochromic spiroheterocyclic compounds.
Chem Rev 104:2751–2776
6. Tamai N, Miyasaka H (2000) Ultrafast dynamics of photochromic systems. Chem Rev
100:1875–1890
7. Natansohn A, Rochon P (2002) Photoinduced motions in azo-containing polymers. Chem Rev
102:4139–4175
8. Bandara HMD, Burdette SC (2012) Photoisomerization in different classes of azobenzene.
Chem Soc Rev 41:1809–1825
9. Priimagi A, Barrett CJ, Shishido A (2014) Recent twists in photoactuation and photoalignment
control. J Mater Chem C 2:7155–7162
10. Hatano S, Abe J (2008) Activation parameters for the recombination reaction of intramolecular
radical pairs generated from the radical diffusion-inhibited HABI Derivative. J Phys Chem A
112:6098–6103
11. Fukaminato T, Sasaki T, Kawai T, Tamai N, Irie M (2004) Digital photoswitching of fluorescence based on the photochromism of diarylethene derivatives at a single-molecule level. J Am
Chem Soc 126:14843–14849
12. Matsuda K, Irie M (2001) Photochromism of diarylethenes with two nitronyl nitroxides:
photoswitching of an intramolecular magnetic interaction. Chem Eur J 7:3466–3473
13. Moriyama Y, Matsuda K, Tanifuji N, Irie S, Irie M (2005) Electrochemical cyclization/cycloreversion reactions of diarylethenes. Org Lett 7:3315–3318
14. Gilat SL, Kawai SH, Lehn JM (1993) Light-triggered electrical and optical switching devices.
J Chem Soc Chem Commun 18:1439–1442
15. Irie M, Kobatake S, Horichi M (2001) Reversible surface morphology changes of a
photochromic diarylethene single crystal by photoirradiation. Science 291:1769–1772