24 Solid-State Polymerization of Conjugated …
521
26. Watanabe, J., Yokoyama, H., Okada, S., Takaragi, S., Matsuda, H., Nakanishi, H.: Solid-state
polymerization of monophenylbutadiyne derivatives. Mol. Cryst. Liq. Cryst. 505, 203–209
(2009)
27. Okada, S., Matsuda, H., Otsuka, M., Nakanishi, H., Kato, M.: Synthesis and solid-state polymerization of ω-(4-aryl-1,3-butadiynyl) substituted 1-alkanol and alkanoic acid. Bull. Chem.
Soc. Jpn. 67, 483–489 (1994)
28. Enkelmann, V., Schleier, G., Wegner, G., Eichele, H., Schwoerer, M.: Structure, luminescence
and polymerization of a diacetylene crystal: 1,6-di-(n-carbazolyl)-2,4 hexadiin (DCH). Chem.
Phys. Lett. 52, 314–319 (1977)
29. Michinobu, T., May, J.C., Lim, J.H., Boudon, C., Gisselbrecht, J.-P., Seiler, P., Gross, M.,
Biaggio, I., Diederich, F.: A new class of organic donor–acceptor molecules with large thirdorder optical nonlinearities. Chem. Commun., 737–739 (2005)
30. Kivala, M., Boudon, C., Gisselbrecht, J.-P., Seiler, P., Gross, M., Diederich, F.: A novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ): Charge-transfer chromophores by [2 + 2]
cycloaddition with alkynes. Chem. Commun., 4731–4733 (2007)
31. Tatewaki, Y., Shibata, H., Shibuya, T., Watanabe, K., Ishii, S., Okada, S.: Solid-state polymerization of a pyrenylbutadiyne derivative. in: Kawabe Y., Kawase M. (eds.) Polymer Photonics
and Novel Optical Technologies, pp. 152–155, Photonics World Consortium, Chitose (2011)
32. Cheng, Q., Yamamoto, M., Stevens, R.C.: Amino acid terminated polydiacetylene lipidmicrostructures: morphology and chromatic transition. Langmuir 16, 5333–5342 (2000)
33. Tatewaki, Y., Sato, A., Ito, S., Inayama, S., Okada, S.: Synthesis and solid-state polymerization
of L-alanine derivatives with a (1-pyrenyl)butadiynyl group. Mol. Cryst. Liq. Cryst. 580, 58–63
(2013)
34. Kasai, H., Nalwa, H.S., Oikawa, H., Okada, S., Matsuda, H., Minami, N., Kakuta, A., Ono, K.,
Mukoh, A., Nakanishi, H.: A novel preparation method of organic microcrystals. Jpn. J. Appl.
Phys. 31, L1132–L1134 (1992)
35. Imai, M., Tatewaki, Y., Okada, S.: Preparation and physical properties of nanoaggregates
composed of charge-transfer complexes containing butadiyne derivatives with tetrathiafulvalene moieties. Jpn. J. Appl. Phys. 53, 05FA02-1–7 (2014)
36. Frankel, D.A., O’Brien, D.F.: Supramolecular assemblies of diacetylenic aldonamides. J. Am.
Chem. Soc. 113, 7436–7437 (1991)
37. Fuhrhop, J.-H., Blumtritt, P., Lehmann, C., Luger, P.: Supramolecular assemblies, a crystal
structure, and a polymer of N-diacetylenic gluconamides. J. Am. Chem. Soc. 113, 7437–7439
(1991)
38. Fujita, N., Sakamoto, Y., Shirakawa, M., Ojima, M., Fujii, A., Ozaki, M., Shinkai, S.: Polydiacetylene Nanofibers Created in Low-Molecular-Weight Gels by Post Modification: Control
of Blue and Red Phases by the Odd − Even Effect in Alkyl Chains. J. Am. Chem. Soc. 129,
4134–4135 (2007)
39. Takahashi, R., Nunokawa, T., Shibuya, T., Tomita, R., Tatewaki, Y., Okada, S., Kimura, T.,
Shimada, S., Matsuda, H.: Synthesis and solid-state polymerization of butadiyne derivatives
with trialkoxyphenylurethane groups. Bull. Chem. Soc. Jpn. 85, 236–244 (2012)
40. Kikuchi, K., Tatewaki, Y., Okada, S.: Self-assembly and solid-state polymerization of butadiyne
derivatives with amide and trialkoxyphenyl groups. Bull. Chem. Soc. Jpn. 90, 298–305 (2017)
41. Matsuzawa, H., Okada, S., Sarkar, A., Matsuda, H., Nakanishi, H.: Synthesis of ladder polymers
containing polydiacetylene backbones connected with methylene chains and their properties.
J. Polym. Sci. Pt. A: Polym. Chem. 37, 3537–3548 (1999)
42. Matsuo, H., Okada, S., Nakanishi, H., Matsuda, H., Takaragi, S.: Solid-state polymerization
of monomers possessing two diphenylbutadiyne moieties with amido groups to form ladder
polymers. Polym. J. 34, 825–834 (2002)
43. Okada, S., Hayamizu, K., Matsuda, H., Masaki, A., Nakanishi, H.: Structures of the polymers obtained by the solid-state polymerization of diyne, triyne, and tetrayne with long alkyl
substituents. Bull. Chem. Soc. Jpn. 64, 857–863 (1991)
44. Okada, S., Matsuda, H., Masaki, A., Nakanishi, H., Hayamizu, K.: Novel linear and ladder
polymers from tetraynes for nonlinear optics. in: Singer K.D. (ed.) Nonlinear Optical Properties
of Organic Materials IV, Proceedings of SPIE, vol. 1560, pp. 25–34, SPIE, Bellingham (1991)
521
26. Watanabe, J., Yokoyama, H., Okada, S., Takaragi, S., Matsuda, H., Nakanishi, H.: Solid-state
polymerization of monophenylbutadiyne derivatives. Mol. Cryst. Liq. Cryst. 505, 203–209
(2009)
27. Okada, S., Matsuda, H., Otsuka, M., Nakanishi, H., Kato, M.: Synthesis and solid-state polymerization of ω-(4-aryl-1,3-butadiynyl) substituted 1-alkanol and alkanoic acid. Bull. Chem.
Soc. Jpn. 67, 483–489 (1994)
28. Enkelmann, V., Schleier, G., Wegner, G., Eichele, H., Schwoerer, M.: Structure, luminescence
and polymerization of a diacetylene crystal: 1,6-di-(n-carbazolyl)-2,4 hexadiin (DCH). Chem.
Phys. Lett. 52, 314–319 (1977)
29. Michinobu, T., May, J.C., Lim, J.H., Boudon, C., Gisselbrecht, J.-P., Seiler, P., Gross, M.,
Biaggio, I., Diederich, F.: A new class of organic donor–acceptor molecules with large thirdorder optical nonlinearities. Chem. Commun., 737–739 (2005)
30. Kivala, M., Boudon, C., Gisselbrecht, J.-P., Seiler, P., Gross, M., Diederich, F.: A novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ): Charge-transfer chromophores by [2 + 2]
cycloaddition with alkynes. Chem. Commun., 4731–4733 (2007)
31. Tatewaki, Y., Shibata, H., Shibuya, T., Watanabe, K., Ishii, S., Okada, S.: Solid-state polymerization of a pyrenylbutadiyne derivative. in: Kawabe Y., Kawase M. (eds.) Polymer Photonics
and Novel Optical Technologies, pp. 152–155, Photonics World Consortium, Chitose (2011)
32. Cheng, Q., Yamamoto, M., Stevens, R.C.: Amino acid terminated polydiacetylene lipidmicrostructures: morphology and chromatic transition. Langmuir 16, 5333–5342 (2000)
33. Tatewaki, Y., Sato, A., Ito, S., Inayama, S., Okada, S.: Synthesis and solid-state polymerization
of L-alanine derivatives with a (1-pyrenyl)butadiynyl group. Mol. Cryst. Liq. Cryst. 580, 58–63
(2013)
34. Kasai, H., Nalwa, H.S., Oikawa, H., Okada, S., Matsuda, H., Minami, N., Kakuta, A., Ono, K.,
Mukoh, A., Nakanishi, H.: A novel preparation method of organic microcrystals. Jpn. J. Appl.
Phys. 31, L1132–L1134 (1992)
35. Imai, M., Tatewaki, Y., Okada, S.: Preparation and physical properties of nanoaggregates
composed of charge-transfer complexes containing butadiyne derivatives with tetrathiafulvalene moieties. Jpn. J. Appl. Phys. 53, 05FA02-1–7 (2014)
36. Frankel, D.A., O’Brien, D.F.: Supramolecular assemblies of diacetylenic aldonamides. J. Am.
Chem. Soc. 113, 7436–7437 (1991)
37. Fuhrhop, J.-H., Blumtritt, P., Lehmann, C., Luger, P.: Supramolecular assemblies, a crystal
structure, and a polymer of N-diacetylenic gluconamides. J. Am. Chem. Soc. 113, 7437–7439
(1991)
38. Fujita, N., Sakamoto, Y., Shirakawa, M., Ojima, M., Fujii, A., Ozaki, M., Shinkai, S.: Polydiacetylene Nanofibers Created in Low-Molecular-Weight Gels by Post Modification: Control
of Blue and Red Phases by the Odd − Even Effect in Alkyl Chains. J. Am. Chem. Soc. 129,
4134–4135 (2007)
39. Takahashi, R., Nunokawa, T., Shibuya, T., Tomita, R., Tatewaki, Y., Okada, S., Kimura, T.,
Shimada, S., Matsuda, H.: Synthesis and solid-state polymerization of butadiyne derivatives
with trialkoxyphenylurethane groups. Bull. Chem. Soc. Jpn. 85, 236–244 (2012)
40. Kikuchi, K., Tatewaki, Y., Okada, S.: Self-assembly and solid-state polymerization of butadiyne
derivatives with amide and trialkoxyphenyl groups. Bull. Chem. Soc. Jpn. 90, 298–305 (2017)
41. Matsuzawa, H., Okada, S., Sarkar, A., Matsuda, H., Nakanishi, H.: Synthesis of ladder polymers
containing polydiacetylene backbones connected with methylene chains and their properties.
J. Polym. Sci. Pt. A: Polym. Chem. 37, 3537–3548 (1999)
42. Matsuo, H., Okada, S., Nakanishi, H., Matsuda, H., Takaragi, S.: Solid-state polymerization
of monomers possessing two diphenylbutadiyne moieties with amido groups to form ladder
polymers. Polym. J. 34, 825–834 (2002)
43. Okada, S., Hayamizu, K., Matsuda, H., Masaki, A., Nakanishi, H.: Structures of the polymers obtained by the solid-state polymerization of diyne, triyne, and tetrayne with long alkyl
substituents. Bull. Chem. Soc. Jpn. 64, 857–863 (1991)
44. Okada, S., Matsuda, H., Masaki, A., Nakanishi, H., Hayamizu, K.: Novel linear and ladder
polymers from tetraynes for nonlinear optics. in: Singer K.D. (ed.) Nonlinear Optical Properties
of Organic Materials IV, Proceedings of SPIE, vol. 1560, pp. 25–34, SPIE, Bellingham (1991)