Chapter 24
Solid-State Polymerization of Conjugated
Acetylene Compounds to Form
π-Conjugated Polymers
Shuji Okada, Yoko Tatewaki, and Ryohei Yamakado
Abstract Since polydiacetylene derivatives are synthesized by the solid-state polymerization of butadiyne monomers, the structures of the monomers determining their
alignment in the crystals are very important. By applying the molecular design strategies to obtain polymerizable monomers, several monomers with interesting structures and properties, i.e., monomers with electron-donating aromatic rings directly
attached to the butadiyne moiety, gel-formable butadiyne monomers with 3,4,5alkyloxyphenyl groups, monomers with a phenylene group sandwiched by two
butadiyne moieties, and a ring monomer with two butadiyne moieties to form a
tubular polymer, were synthesized and characterized.
Keywords Acetylenic compound · Solid-state polymerization · Polydiacetylene ·
Donor substituent · Gel · Tubular polymer
24.1 Introduction
π- Conjugated polymers are quite important materials for electronics and photonics,
and their applications are based on electrical conducting and semiconducting properties, linear and nonlinear optical properties, photovoltaic property, etc. Similar to
conventional polymers, most of π-conjugated polymers are synthesized in the solution state. Meanwhile, polydiacetylene is a unique π-conjugated polymer obtained
by the solid-state polymerization of butadiyne monomers. Although some butadiyne
monomers have been known to give colored materials in their crystalline states [1],
S. Okada (B) · R. Yamakado
Graduate School of Organic Materials Science, Yamagata University, 4-3-16 Jonan,
Yonezawa 992-8510, Japan
e-mail: okadas@yz.yamagata-u.ac.jp
R. Yamakado
e-mail: yamakado@yz.yamagata-u.ac.jp
Y. Tatewaki
Division of Applied Chemistry, Tokyo University of Agriculture and Technology,
2-24-16 Naka-Cho, Koganei 184-8588, Japan
e-mail: ytatewa@cc.tuat.ac.jp
© Springer Nature Singapore Pte Ltd. 2020
M. Sakamoto and H. Uekusa (eds.), Advances in Organic Crystal Chemistry,
https://doi.org/10.1007/978-981-15-5085-0_24
501
Solid-State Polymerization of Conjugated
Acetylene Compounds to Form
π-Conjugated Polymers
Shuji Okada, Yoko Tatewaki, and Ryohei Yamakado
Abstract Since polydiacetylene derivatives are synthesized by the solid-state polymerization of butadiyne monomers, the structures of the monomers determining their
alignment in the crystals are very important. By applying the molecular design strategies to obtain polymerizable monomers, several monomers with interesting structures and properties, i.e., monomers with electron-donating aromatic rings directly
attached to the butadiyne moiety, gel-formable butadiyne monomers with 3,4,5alkyloxyphenyl groups, monomers with a phenylene group sandwiched by two
butadiyne moieties, and a ring monomer with two butadiyne moieties to form a
tubular polymer, were synthesized and characterized.
Keywords Acetylenic compound · Solid-state polymerization · Polydiacetylene ·
Donor substituent · Gel · Tubular polymer
24.1 Introduction
π- Conjugated polymers are quite important materials for electronics and photonics,
and their applications are based on electrical conducting and semiconducting properties, linear and nonlinear optical properties, photovoltaic property, etc. Similar to
conventional polymers, most of π-conjugated polymers are synthesized in the solution state. Meanwhile, polydiacetylene is a unique π-conjugated polymer obtained
by the solid-state polymerization of butadiyne monomers. Although some butadiyne
monomers have been known to give colored materials in their crystalline states [1],
S. Okada (B) · R. Yamakado
Graduate School of Organic Materials Science, Yamagata University, 4-3-16 Jonan,
Yonezawa 992-8510, Japan
e-mail: okadas@yz.yamagata-u.ac.jp
R. Yamakado
e-mail: yamakado@yz.yamagata-u.ac.jp
Y. Tatewaki
Division of Applied Chemistry, Tokyo University of Agriculture and Technology,
2-24-16 Naka-Cho, Koganei 184-8588, Japan
e-mail: ytatewa@cc.tuat.ac.jp
© Springer Nature Singapore Pte Ltd. 2020
M. Sakamoto and H. Uekusa (eds.), Advances in Organic Crystal Chemistry,
https://doi.org/10.1007/978-981-15-5085-0_24
501