558
I. Osaka
Green MA, Ho-Baillie A, Snaith HJ (2014) The emergence of perovskite solar cells. Nat Photon
8:506–514
Imai K, Kurihara M, Mathias L, Wittmann J, Alston WB, Stille JK (1973) Synthesis and properties
of thermally stable ladder polymers containing the 1,4-pyrazine ring obtained from polyheterocyclizations of tetramines and tetraketones in poly(phosphoric acid) and m-cresol. Macromolecules
6:158–162
Kawashima K, Miyazaki E, Shimawaki M, Inoue Y, Mori H, Takemura N, Osaka I, Takimiya K
(2013) 5,10-diborylated naphtho[1,2-c:5,6-c ]bis[1,2,5]thiadiazole: a ready-to-use precursor for
the synthesis of high-performance semiconducting polymers. Polym Chem 4:5224–5227
Kawashima K, Osaka I, Takimiya K (2015a) Effect of chalcogen atom on the properties of
naphthobischalcogenadiazole-based π-conjugated polymers. Chem Mater 27:6558–6570
Kawashima K, Tamai Y, Ohkita H, Osaka I, Takimiya K (2015b) High-efficiency polymer solar
cells with small photon energy loss. Nat Commun 6:10085
Kawashima K, Fukuhara T, Suda Y, Suzuki Y, Koganezawa T, Yoshida H, Ohkita H, Osaka I,
Takimiya K (2016) Implication of fluorine atom on electronic properties, ordering structures,
and photovoltaic performance in naphthobisthiadiazole-based semiconducting polymers. J Am
Chem Soc 138:10265–10275
King RR, Bhusari D, Boca A, Larrabee D, Liu XQ, Hong W, Fetzer CM, Law DC, Karam NH
(2011) Band gap-voltage offset and energy production in next-generation multijunction solar
cells. Prog Photovolt 19:797–812
Li W, Hendriks KH, Furlan A, Wienk MM, Janssen RAJ (2015) High quantum efficiencies in
polymer solar cells at energy losses below 0.6 eV. J Am Chem Soc 137:2231–2234
Mataka S, Takahashi K, Ikezaki Y, Hatta T, Tori-i A, Tashiro M (1991) Sulfur nitride in organic
chemsitry. XIV, Selective formation of benzo-and benzobis [1, 2, 5] thiadiazole skeleton in the
reaction of tetrasulfur tetranitride with naphthalenols and related compounds. Bull Chem Soc Jpn
64:68–73
McCullough RD (1998) The chemistry of conducting polythiophenes. Adv Mater 10:93–116
Mikie T, Osaka I (2018) Selective synthesis and properties of electron-deficient hybrid naphthalenebased π-conjugated systems. Chem Eur J 24:19228–19235
Mikie T, Osaka I (2019) Ester-Functionalized naphthobispyrazine as an acceptor building unit for
semiconducting polymers: synthesis, properties, and photovoltaic performance. Macromolecules
52:3909–3917
Mikie T, Kawashima K, Komeyama K, Yoshida H, Osaka I (2017) Naphthobispyrazine as an
electron-deficient building unit for π-conjugated polymers: efficient synthesis and polymer
properties. Chem Lett 46:1193–1196
Osaka I, Takimiya K (2017) Naphthobischalcogenadiazole conjugated polymers: emerging materials for organic electronics. Adv Mater 39:1605218
Osaka I, Shimawaki M, Mori H, Doi I, Miyazaki E, Koganezawa T, Takimiya K (2012) Synthesis,
characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based
semiconducting polymer. J Am Chem Soc 134:3498–3507
Osaka I, Saito M, Koganezawa T, Takimiya K (2014) Thiophene-thiazolothiazole copolymers:
significant impact of side chain composition on backbone orientation and solar cell performances.
Adv Mater 26:331–338
Peet J, Wen L, Byrne P, Rodman S, Forberich K, Shao Y, Drolet N, Gaudiana R, Dennler G, Waller
D (2011) Bulk heterojunction solar cells with thick active layers and high fill factors enabled by
a bithiophene-co-thiazolothiazole push-pull copolymer. Appl Phys Lett 98:043301
Reynolds JR, Thompson BC, Skotheim TA (2019) Handbook of conducting polymers, 4th ed. CRC
Press
Saito M, Koganezawa T, Osaka I (2018) Correlation between distribution of polymer orientation
and cell structure in organic photovoltaics. ACS Appl Mater Interfaces 10:32420–32425
Thompson BC, Fréchet JMJ (2008) Polymer-fullerene composite solar cells. Angew Chem Int Ed
47:58–77
I. Osaka
Green MA, Ho-Baillie A, Snaith HJ (2014) The emergence of perovskite solar cells. Nat Photon
8:506–514
Imai K, Kurihara M, Mathias L, Wittmann J, Alston WB, Stille JK (1973) Synthesis and properties
of thermally stable ladder polymers containing the 1,4-pyrazine ring obtained from polyheterocyclizations of tetramines and tetraketones in poly(phosphoric acid) and m-cresol. Macromolecules
6:158–162
Kawashima K, Miyazaki E, Shimawaki M, Inoue Y, Mori H, Takemura N, Osaka I, Takimiya K
(2013) 5,10-diborylated naphtho[1,2-c:5,6-c ]bis[1,2,5]thiadiazole: a ready-to-use precursor for
the synthesis of high-performance semiconducting polymers. Polym Chem 4:5224–5227
Kawashima K, Osaka I, Takimiya K (2015a) Effect of chalcogen atom on the properties of
naphthobischalcogenadiazole-based π-conjugated polymers. Chem Mater 27:6558–6570
Kawashima K, Tamai Y, Ohkita H, Osaka I, Takimiya K (2015b) High-efficiency polymer solar
cells with small photon energy loss. Nat Commun 6:10085
Kawashima K, Fukuhara T, Suda Y, Suzuki Y, Koganezawa T, Yoshida H, Ohkita H, Osaka I,
Takimiya K (2016) Implication of fluorine atom on electronic properties, ordering structures,
and photovoltaic performance in naphthobisthiadiazole-based semiconducting polymers. J Am
Chem Soc 138:10265–10275
King RR, Bhusari D, Boca A, Larrabee D, Liu XQ, Hong W, Fetzer CM, Law DC, Karam NH
(2011) Band gap-voltage offset and energy production in next-generation multijunction solar
cells. Prog Photovolt 19:797–812
Li W, Hendriks KH, Furlan A, Wienk MM, Janssen RAJ (2015) High quantum efficiencies in
polymer solar cells at energy losses below 0.6 eV. J Am Chem Soc 137:2231–2234
Mataka S, Takahashi K, Ikezaki Y, Hatta T, Tori-i A, Tashiro M (1991) Sulfur nitride in organic
chemsitry. XIV, Selective formation of benzo-and benzobis [1, 2, 5] thiadiazole skeleton in the
reaction of tetrasulfur tetranitride with naphthalenols and related compounds. Bull Chem Soc Jpn
64:68–73
McCullough RD (1998) The chemistry of conducting polythiophenes. Adv Mater 10:93–116
Mikie T, Osaka I (2018) Selective synthesis and properties of electron-deficient hybrid naphthalenebased π-conjugated systems. Chem Eur J 24:19228–19235
Mikie T, Osaka I (2019) Ester-Functionalized naphthobispyrazine as an acceptor building unit for
semiconducting polymers: synthesis, properties, and photovoltaic performance. Macromolecules
52:3909–3917
Mikie T, Kawashima K, Komeyama K, Yoshida H, Osaka I (2017) Naphthobispyrazine as an
electron-deficient building unit for π-conjugated polymers: efficient synthesis and polymer
properties. Chem Lett 46:1193–1196
Osaka I, Takimiya K (2017) Naphthobischalcogenadiazole conjugated polymers: emerging materials for organic electronics. Adv Mater 39:1605218
Osaka I, Shimawaki M, Mori H, Doi I, Miyazaki E, Koganezawa T, Takimiya K (2012) Synthesis,
characterization, and transistor and solar cell applications of a naphthobisthiadiazole-based
semiconducting polymer. J Am Chem Soc 134:3498–3507
Osaka I, Saito M, Koganezawa T, Takimiya K (2014) Thiophene-thiazolothiazole copolymers:
significant impact of side chain composition on backbone orientation and solar cell performances.
Adv Mater 26:331–338
Peet J, Wen L, Byrne P, Rodman S, Forberich K, Shao Y, Drolet N, Gaudiana R, Dennler G, Waller
D (2011) Bulk heterojunction solar cells with thick active layers and high fill factors enabled by
a bithiophene-co-thiazolothiazole push-pull copolymer. Appl Phys Lett 98:043301
Reynolds JR, Thompson BC, Skotheim TA (2019) Handbook of conducting polymers, 4th ed. CRC
Press
Saito M, Koganezawa T, Osaka I (2018) Correlation between distribution of polymer orientation
and cell structure in organic photovoltaics. ACS Appl Mater Interfaces 10:32420–32425
Thompson BC, Fréchet JMJ (2008) Polymer-fullerene composite solar cells. Angew Chem Int Ed
47:58–77