250
T. Kawai
On the other hand, the chain-like ring-cycloreversion reactions seem to be a spectacle example of amplification molecular system. The chain-propagation number is
not obviously limited by the reaction thermodynamics but by competitive kinetics
of chain-propagation dynamics with the spontaneous decay of radicals. Control on
radical lifetime and appropriate design of reaction space may offer the ultimate
challenging fields.
Acknowledgements We deeply appreciate to Professors M. Irie, H. Miyasaka, J. Abe, K. Matsuda,
N. Nakatani, R. Metivier T. Nakashima, for their collaboration. The present work was supported
by JSPS KAKENHI Grant Number 26107002, Grant-in-Aid for Scientific Research on Innovative
Areas “Photosynergetics”.
References
1. Hille B (2001) Ionic channels of excitable membranes. Oxford University Press Inc
2. Kliger DS, Menger EL (1975) Special issue on the chemistry of vision. Acc Chem Res 8:81–84
3. Kim JE, Tauber MJ, Mathies RA (2001) Wavelength dependent cis-trans isomerization in
vision. Biochemistry 40:13774–13778
4. Fouassier JP, Lalevee J (2012) Photoinitiators for polymer synthesis-scope, reactivity, and
efficiency. Wiley-VCH, Weinheim
5. Velema WA, Szymanski W, Feringa BL (2014) Photopharmacology: beyond proof of principle.
J Am Chem Soc 136:62178–62191
6. Irie M, Mohri M (1988) Thermally irreversible photochromic systems. Reversible photocyclization of diarylethene derivatives. J Org Chem 53:803–808
7. Irie M, Yokoyama Y, Seki T (2013) New frontiers in photochromism. Tokyo, Springer Japan
8. Kawai T, Iseda T, Irie M (2004) Photochromism of triangle terthiophene derivatives as
molecular re-router. Chem Commun 72–73
9. Nakashima T, Atsumi K, Kawai S, Nakagawa T, Hasegawa Y, Kawai T (2007) Photochromism
of thiazole-containing triangle terarylenes. Eur J Org Chem 2007:3212–3218
10. Irie M (2000) diarylethenes for memories and switches. Chem Rev 100:1685–1716
11. Irie M, Fukaminato T, Matsuda K, Kobatake S (2014) Photochromism of diarylethene
molecules and crystals: memories, switches, and actuators. Chem Rev 114:12174–12277
12. Tian H, Chen B, Tu H, Müllen K (2002) Novel bisthienylethene-based photochromic
tetraazaporphyrin with photoregulating luminescence. Adv Mater 14:918
13. Krayushkin MM, Ivanov SN, Martynkin AY, Lichitsky BV, Dudinov AA, Uzhinov BM (2002)
Photochromic dihetarylethenes. 17. Synthesis and photochromic properties of dithienylethenes
containing new heterocyclic bridging fragments. Russ Chem Bull 50:116–121
14. Kawai S, Nakashima T, Atsumi K, Sakai T, Harigai M, Imamoto Y, Kamikubo H, Kataoka
M, Kawai T (2007) Novel photochromic molecules based on 4,5-dithienyl thiazole with fast
thermal bleaching rate. Chem Mater 19:3479–3483
15. Fukumoto S, Nakashima T, Kawai T (2011) Photon- quantitative reaction of a dithiazolylarylene
in solution. Angew Chem Int Ed 50:1565–1568
16. Nakashima T, Fujii R, Kawai T (2011) Regulation of folding and photochromic reactivity of
terarylenes through a host–guest interaction. Chem Eur J 17:10951–10957
17. Nakashima T, Yamamoto K, Kimura Y, Kawai T (2013) Chiral photoresponsive tetrathiazoles
that provide snapshots of folding states. Chem Eur J 19:16972–16980
18. Hashimoto M, Nakashima T, Kuno J, Yamada M, Kawai T (2018) Dynamic modulation of
circularly polarized luminescence in photoresponsive assemblies. Chem Nano Mat 4:815–820
T. Kawai
On the other hand, the chain-like ring-cycloreversion reactions seem to be a spectacle example of amplification molecular system. The chain-propagation number is
not obviously limited by the reaction thermodynamics but by competitive kinetics
of chain-propagation dynamics with the spontaneous decay of radicals. Control on
radical lifetime and appropriate design of reaction space may offer the ultimate
challenging fields.
Acknowledgements We deeply appreciate to Professors M. Irie, H. Miyasaka, J. Abe, K. Matsuda,
N. Nakatani, R. Metivier T. Nakashima, for their collaboration. The present work was supported
by JSPS KAKENHI Grant Number 26107002, Grant-in-Aid for Scientific Research on Innovative
Areas “Photosynergetics”.
References
1. Hille B (2001) Ionic channels of excitable membranes. Oxford University Press Inc
2. Kliger DS, Menger EL (1975) Special issue on the chemistry of vision. Acc Chem Res 8:81–84
3. Kim JE, Tauber MJ, Mathies RA (2001) Wavelength dependent cis-trans isomerization in
vision. Biochemistry 40:13774–13778
4. Fouassier JP, Lalevee J (2012) Photoinitiators for polymer synthesis-scope, reactivity, and
efficiency. Wiley-VCH, Weinheim
5. Velema WA, Szymanski W, Feringa BL (2014) Photopharmacology: beyond proof of principle.
J Am Chem Soc 136:62178–62191
6. Irie M, Mohri M (1988) Thermally irreversible photochromic systems. Reversible photocyclization of diarylethene derivatives. J Org Chem 53:803–808
7. Irie M, Yokoyama Y, Seki T (2013) New frontiers in photochromism. Tokyo, Springer Japan
8. Kawai T, Iseda T, Irie M (2004) Photochromism of triangle terthiophene derivatives as
molecular re-router. Chem Commun 72–73
9. Nakashima T, Atsumi K, Kawai S, Nakagawa T, Hasegawa Y, Kawai T (2007) Photochromism
of thiazole-containing triangle terarylenes. Eur J Org Chem 2007:3212–3218
10. Irie M (2000) diarylethenes for memories and switches. Chem Rev 100:1685–1716
11. Irie M, Fukaminato T, Matsuda K, Kobatake S (2014) Photochromism of diarylethene
molecules and crystals: memories, switches, and actuators. Chem Rev 114:12174–12277
12. Tian H, Chen B, Tu H, Müllen K (2002) Novel bisthienylethene-based photochromic
tetraazaporphyrin with photoregulating luminescence. Adv Mater 14:918
13. Krayushkin MM, Ivanov SN, Martynkin AY, Lichitsky BV, Dudinov AA, Uzhinov BM (2002)
Photochromic dihetarylethenes. 17. Synthesis and photochromic properties of dithienylethenes
containing new heterocyclic bridging fragments. Russ Chem Bull 50:116–121
14. Kawai S, Nakashima T, Atsumi K, Sakai T, Harigai M, Imamoto Y, Kamikubo H, Kataoka
M, Kawai T (2007) Novel photochromic molecules based on 4,5-dithienyl thiazole with fast
thermal bleaching rate. Chem Mater 19:3479–3483
15. Fukumoto S, Nakashima T, Kawai T (2011) Photon- quantitative reaction of a dithiazolylarylene
in solution. Angew Chem Int Ed 50:1565–1568
16. Nakashima T, Fujii R, Kawai T (2011) Regulation of folding and photochromic reactivity of
terarylenes through a host–guest interaction. Chem Eur J 17:10951–10957
17. Nakashima T, Yamamoto K, Kimura Y, Kawai T (2013) Chiral photoresponsive tetrathiazoles
that provide snapshots of folding states. Chem Eur J 19:16972–16980
18. Hashimoto M, Nakashima T, Kuno J, Yamada M, Kawai T (2018) Dynamic modulation of
circularly polarized luminescence in photoresponsive assemblies. Chem Nano Mat 4:815–820