18
M. Matsui
X
N
R
N
R
H 3 C
CH 3
H 3 C CH 3
1.66
X
(CF 3 SO 2 ) 2 N
I
(CF 3 SO 2 ) 2 N
(C 4 F 9 SO 2 ) 2 N
R
CH 3
C 3 H 7
C 3 H 7
C 3 H 7
F max / nm Φ
Φ
573
578
574
574
f
0.07
0.04
0.12
0.12
In toluene
F max / nm
648
677
657
648
f
0.03
0.03
0.31
0.02
Solid state (crystalline)
Fig. 1.14 Solid-state fluorescence of trimethine dyes
of this compound indicates an isolated monomer-type packing that comes from the
anion and propyl groups, whereas the other derivatives show the isolated dimer-type
packing or consequent π/π stacking (Matsui et al. 2015).
References
Biradar S, Kasugai R, Kanoh H, Nagao H, Kubota Y, Funabiki K, Shiro M, Matsui M (2016) Liquid
azo dyes. Dyes Pigm. 125:249
Higashijima S, Miura H, Fujita T, Kubota Y, Funabiki K, Yoshida T, Matsui M (2011) Highly efficient
new indoline dye having strong electron-withdrawing group for zinc oxide dye-sensitized solar
cell. Tetrahedron 67:6289
Higashijima S, Inoue Y, Miura H, Kubota Y, Funabiki K, Yoshida T, Matsui M (2012) Organic dyes
containing fluorene-substituted indoline core for zinc oxide dye-sensitized solar cell. RSC Adv.
2:2721
Hishiki Y (1974) Recent progress in cyanine dyes syntheses. Yuki Gosei Kyokai Shi 32:971
Horiuchi T, Miura H, Uchida S (2003) Highly-efficient metal-free organic dyes for dye-sensitized
solar cells. Chem Commun 3036
Ito S, Miura H, Uchida S, Takata M, Sumioka K, Liska P, Comte P, Péchy P, Grätzel M (2008)
High-conversion-efficiency organic dye-sensitized solar cells with a novel indoline dye. Chem
Commun 5194
Kasha M, Rawls HR, El-Bayoumi MA (1965) The exciton model in molecular spectoscopy. Pure
Appl Chem 11:371
König W (1922) Chemistry of the quinocyanines. Constitution of the pinacyanoles. Ber 55:3293
Matsui M, Kubota Y, Funabiki K (2014a) Low melting-point 2-pyridinium styryl dyes. J Jpn Soc
Colour Mater 87:3
Matsui M, Kubota Y, Funabiki K (2014b) Liquid 2-pyridinium styryl dyes having oxaalkyl units. J
Jpn Soc Colour Mater 87:187
Matsui M, Ando S, Fukushima M, Shibata T, Kubota Y, Funabiki K (2015) Fluorescence properties
of indolenium carbocyanine dyes in solid state. Tetrahedron 71:3728
M. Matsui
X
N
R
N
R
H 3 C
CH 3
H 3 C CH 3
1.66
X
(CF 3 SO 2 ) 2 N
I
(CF 3 SO 2 ) 2 N
(C 4 F 9 SO 2 ) 2 N
R
CH 3
C 3 H 7
C 3 H 7
C 3 H 7
F max / nm Φ
Φ
573
578
574
574
f
0.07
0.04
0.12
0.12
In toluene
F max / nm
648
677
657
648
f
0.03
0.03
0.31
0.02
Solid state (crystalline)
Fig. 1.14 Solid-state fluorescence of trimethine dyes
of this compound indicates an isolated monomer-type packing that comes from the
anion and propyl groups, whereas the other derivatives show the isolated dimer-type
packing or consequent π/π stacking (Matsui et al. 2015).
References
Biradar S, Kasugai R, Kanoh H, Nagao H, Kubota Y, Funabiki K, Shiro M, Matsui M (2016) Liquid
azo dyes. Dyes Pigm. 125:249
Higashijima S, Miura H, Fujita T, Kubota Y, Funabiki K, Yoshida T, Matsui M (2011) Highly efficient
new indoline dye having strong electron-withdrawing group for zinc oxide dye-sensitized solar
cell. Tetrahedron 67:6289
Higashijima S, Inoue Y, Miura H, Kubota Y, Funabiki K, Yoshida T, Matsui M (2012) Organic dyes
containing fluorene-substituted indoline core for zinc oxide dye-sensitized solar cell. RSC Adv.
2:2721
Hishiki Y (1974) Recent progress in cyanine dyes syntheses. Yuki Gosei Kyokai Shi 32:971
Horiuchi T, Miura H, Uchida S (2003) Highly-efficient metal-free organic dyes for dye-sensitized
solar cells. Chem Commun 3036
Ito S, Miura H, Uchida S, Takata M, Sumioka K, Liska P, Comte P, Péchy P, Grätzel M (2008)
High-conversion-efficiency organic dye-sensitized solar cells with a novel indoline dye. Chem
Commun 5194
Kasha M, Rawls HR, El-Bayoumi MA (1965) The exciton model in molecular spectoscopy. Pure
Appl Chem 11:371
König W (1922) Chemistry of the quinocyanines. Constitution of the pinacyanoles. Ber 55:3293
Matsui M, Kubota Y, Funabiki K (2014a) Low melting-point 2-pyridinium styryl dyes. J Jpn Soc
Colour Mater 87:3
Matsui M, Kubota Y, Funabiki K (2014b) Liquid 2-pyridinium styryl dyes having oxaalkyl units. J
Jpn Soc Colour Mater 87:187
Matsui M, Ando S, Fukushima M, Shibata T, Kubota Y, Funabiki K (2015) Fluorescence properties
of indolenium carbocyanine dyes in solid state. Tetrahedron 71:3728