Chapter 15
Creation of Molecularly Integrated
Multi-responsive Photochromic Systems
Yasushi Yokoyama
Abstract In this chapter, we describe: (1) the use of photochromic acid-generating
spiropyran in (i) controlling the absorption wavelength of bisphenanthrolinodiarylethene and (ii) the on/off switching of photochromism in a diarylethene; (2)
highly enantioselective light-induced chirality transfer from human serum albumin
to diarylethenes and (3) the short-step assembly of (i) thermally irreversible stealth
photochromic arylbutadienes and (ii) thermally reversible photochromic teraryls by
way of “click” Huisgen reactions catalyzed by Ru(I) complexes.
Keywords Diarylethene · Spiropyran · Arylbutadiene · Teraryl · Human serum
albumin · McMurry coupling · Huisgen click reaction
15.1 Introduction
Photochromism is an interesting field of research since irradiation of photochromic
materials not only induces changes of color but also various useful properties [1–
5]. Of such photochromic materials, diarylethenes are among the most investigated
[6–8] due to their high thermal as well as photochemical durability, facile synthetic
accessibility and wide range of switching abilities of their color and properties.
Here, we have described our results mainly related to diarylethenes and their
derivatives obtained from the JSPS Kakenhi project on “Photosynergetics” led by
Professor Miyasaka of Osaka University. When the project started in 2014, our
main objective was to construct multifunctional photochromic systems which are
composed of more than one chemical species. The components of such a system
must work in a synergetic manner by photoirradiation to act as a photoswitch for
such novel functions and properties strongly related to photochromic phenomena
(Sect. 15.2) as well as for the transfer of chiral information from its environment
Y. Yokoyama (B)
Graduate School of Engineering Science, Department of Chemistry and Life Science, Yokohama
National University, Yokohama, Kanagawa 240-8501, Japan
e-mail: yokoyama-yasushi-wp@ynu.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_15
253
Creation of Molecularly Integrated
Multi-responsive Photochromic Systems
Yasushi Yokoyama
Abstract In this chapter, we describe: (1) the use of photochromic acid-generating
spiropyran in (i) controlling the absorption wavelength of bisphenanthrolinodiarylethene and (ii) the on/off switching of photochromism in a diarylethene; (2)
highly enantioselective light-induced chirality transfer from human serum albumin
to diarylethenes and (3) the short-step assembly of (i) thermally irreversible stealth
photochromic arylbutadienes and (ii) thermally reversible photochromic teraryls by
way of “click” Huisgen reactions catalyzed by Ru(I) complexes.
Keywords Diarylethene · Spiropyran · Arylbutadiene · Teraryl · Human serum
albumin · McMurry coupling · Huisgen click reaction
15.1 Introduction
Photochromism is an interesting field of research since irradiation of photochromic
materials not only induces changes of color but also various useful properties [1–
5]. Of such photochromic materials, diarylethenes are among the most investigated
[6–8] due to their high thermal as well as photochemical durability, facile synthetic
accessibility and wide range of switching abilities of their color and properties.
Here, we have described our results mainly related to diarylethenes and their
derivatives obtained from the JSPS Kakenhi project on “Photosynergetics” led by
Professor Miyasaka of Osaka University. When the project started in 2014, our
main objective was to construct multifunctional photochromic systems which are
composed of more than one chemical species. The components of such a system
must work in a synergetic manner by photoirradiation to act as a photoswitch for
such novel functions and properties strongly related to photochromic phenomena
(Sect. 15.2) as well as for the transfer of chiral information from its environment
Y. Yokoyama (B)
Graduate School of Engineering Science, Department of Chemistry and Life Science, Yokohama
National University, Yokohama, Kanagawa 240-8501, Japan
e-mail: yokoyama-yasushi-wp@ynu.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_15
253