358
H. Katagiri
27. Ito, S., Kubo, T., Morita, N., Matsui, Y., Watanabe, T., Ohta, A., Fujimori, K., Murafuji,
T., Sugihara, Y., Tajiri, A.: Preparation of azulenyllithium and magnesium reagents utilizing
halogen–metal exchange reaction of several iodoazulenes with organolithium or magnesium
ate complex. Tetrahedron Lett. 45, 2891–2894 (2004)
28. McDonald, R.N., Richmond, J.M., Curtis, J.R., Petty, H.E., Hoskins, T.L., Tajiri, A.: Nonbenzenoid aromatic systems. XII. Synthesis of 2-, 3-, and 6-substituted 2-(1-azulyl)ethanols and
their tosylate esters. J. Org. Chem. 41, 1811–1821 (1976)
29. Kurotobi, K., Tabata, H., Miyauchi, M., Murafuji, T., Sugihara, Y.: Coupling reaction of
azulenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes with haloazulenes. Synthesis 2002, 1013–
1016 (2002)
30. Robinson, R.E., Holovics, T.C., Deplazes, S.F., Powell, D.R., Lushington, G.H., Thompson,
W.H., Barybin, M.V.: Five possible isocyanoazulenes and electron-rich complexes thereof:
a quantitative organometallic approach for probing electronic inhomogeneity of the azulenic
framework. Organometallics 24, 2386–2397 (2005)
31. Saitoh, M., Yano, J., NAKAZAWA, T., Sugihara, Y., Hashimoto, K.: Voltammetric behavior and
electronic molecular structures of several azulenylketones. J. Electroanal. Chem. 418, 139–145
(1996)
32. Yao, J., Cai, Z., Liu, Z., Yu, C., Luo, H., Yang, Y., Yang, S., Zhang, G., Zhang, D.: Tuning
the semiconducting behaviors of new alternating dithienyldiketopyrrolopyrrole-azulene conjugated polymers by varying the linking positions of azulene. Macromolecules 48, 2039–2047
(2015)
33. Xin, H., Ge, C., Yang, X., Gao, H., Yang, X., Gao, X.: Biazulene diimides: a new building
block for organic electronic materials. Chem. Sci. 7, 6701–6705 (2016)
34. Xin, H., Ge, C., Jiao, X., Yang, X., Rundel, K., McNeill, C.R., Gao, X.: Incorporation of 2,6connected azulene units into the backbone of conjugated polymers: towards high-performance
organic optoelectronic materials. Angew. Chem. Int. Ed. 57, 1322–1326 (2017)
35. Xin, H., Li, J., Ge, C., Yang, X., Xue, T., Gao, X.: 6,6 -diaryl-substituted biazulene diimides for
solution-processable high-performance n-type organic semiconductors. Mater. Chem. Front.
2, 975–985 (2018)
36. Umeyama, T., Watanabe, Y., Miyata, T., Imahori, H.: Electron-rich five-membered ring of
azulene as a donor unit in donor-acceptor alternating copolymers for polymer solar cell
applications. Chem. Lett. 44, 47–49 (2015)
37. Nishimura, H., Ishida, N., Shimazaki, A., Wakamiya, A., Saeki, A., Scott, L.T., Murata, Y.:
Hole-transporting materials with a two-dimensionally expanded π-system around an azulene
core for efficient perovskite solar cells. J. Am. Chem. Soc. 137, 15656–15659 (2015)
38. Truong, M.A., Lee, J., Nakamura, T., Seo, J.Y., Jung, M., Ozaki, M., Shimazaki, A., Shioya,
N., Hasegawa, T., Murata, Y., Zakeeruddin, S.M., Grätzel, M., Murdey, R., Wakamiya, A.:
Influence of alkoxy chain length on the properties of two-dimensionally expanded azulenecore-based hole-transporting materials for efficient perovskite solar cells. Chem. Eur. J. 25,
6741–6752 (2019)
H. Katagiri
27. Ito, S., Kubo, T., Morita, N., Matsui, Y., Watanabe, T., Ohta, A., Fujimori, K., Murafuji,
T., Sugihara, Y., Tajiri, A.: Preparation of azulenyllithium and magnesium reagents utilizing
halogen–metal exchange reaction of several iodoazulenes with organolithium or magnesium
ate complex. Tetrahedron Lett. 45, 2891–2894 (2004)
28. McDonald, R.N., Richmond, J.M., Curtis, J.R., Petty, H.E., Hoskins, T.L., Tajiri, A.: Nonbenzenoid aromatic systems. XII. Synthesis of 2-, 3-, and 6-substituted 2-(1-azulyl)ethanols and
their tosylate esters. J. Org. Chem. 41, 1811–1821 (1976)
29. Kurotobi, K., Tabata, H., Miyauchi, M., Murafuji, T., Sugihara, Y.: Coupling reaction of
azulenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolanes with haloazulenes. Synthesis 2002, 1013–
1016 (2002)
30. Robinson, R.E., Holovics, T.C., Deplazes, S.F., Powell, D.R., Lushington, G.H., Thompson,
W.H., Barybin, M.V.: Five possible isocyanoazulenes and electron-rich complexes thereof:
a quantitative organometallic approach for probing electronic inhomogeneity of the azulenic
framework. Organometallics 24, 2386–2397 (2005)
31. Saitoh, M., Yano, J., NAKAZAWA, T., Sugihara, Y., Hashimoto, K.: Voltammetric behavior and
electronic molecular structures of several azulenylketones. J. Electroanal. Chem. 418, 139–145
(1996)
32. Yao, J., Cai, Z., Liu, Z., Yu, C., Luo, H., Yang, Y., Yang, S., Zhang, G., Zhang, D.: Tuning
the semiconducting behaviors of new alternating dithienyldiketopyrrolopyrrole-azulene conjugated polymers by varying the linking positions of azulene. Macromolecules 48, 2039–2047
(2015)
33. Xin, H., Ge, C., Yang, X., Gao, H., Yang, X., Gao, X.: Biazulene diimides: a new building
block for organic electronic materials. Chem. Sci. 7, 6701–6705 (2016)
34. Xin, H., Ge, C., Jiao, X., Yang, X., Rundel, K., McNeill, C.R., Gao, X.: Incorporation of 2,6connected azulene units into the backbone of conjugated polymers: towards high-performance
organic optoelectronic materials. Angew. Chem. Int. Ed. 57, 1322–1326 (2017)
35. Xin, H., Li, J., Ge, C., Yang, X., Xue, T., Gao, X.: 6,6 -diaryl-substituted biazulene diimides for
solution-processable high-performance n-type organic semiconductors. Mater. Chem. Front.
2, 975–985 (2018)
36. Umeyama, T., Watanabe, Y., Miyata, T., Imahori, H.: Electron-rich five-membered ring of
azulene as a donor unit in donor-acceptor alternating copolymers for polymer solar cell
applications. Chem. Lett. 44, 47–49 (2015)
37. Nishimura, H., Ishida, N., Shimazaki, A., Wakamiya, A., Saeki, A., Scott, L.T., Murata, Y.:
Hole-transporting materials with a two-dimensionally expanded π-system around an azulene
core for efficient perovskite solar cells. J. Am. Chem. Soc. 137, 15656–15659 (2015)
38. Truong, M.A., Lee, J., Nakamura, T., Seo, J.Y., Jung, M., Ozaki, M., Shimazaki, A., Shioya,
N., Hasegawa, T., Murata, Y., Zakeeruddin, S.M., Grätzel, M., Murdey, R., Wakamiya, A.:
Influence of alkoxy chain length on the properties of two-dimensionally expanded azulenecore-based hole-transporting materials for efficient perovskite solar cells. Chem. Eur. J. 25,
6741–6752 (2019)