296
T. Mutai
62. Park, S., Park, J., Seo, S.H., Kim, S.Y.: Park, tetraphenylimidazole-based excited-state
intramolecular proton-transfer molecules for highly efficient blue electroluminescence. Adv.
Funct. Mater. 18, 726–731 (2008)
63. Hu, Y., Zhang, Y., Liang, F., Wang, L., Ma, D., Jing, X.: Blue organic light-emitting diodes
based on an oxadiazole-containing organic molecule exhibiting excited state intramolecular
proton transfer. Synth. Met. 137, 1123–1124 (2003)
64. Park, S., Ji, E.K., Se, H.K., Seo, J., Chung, K., Park, S.Y., Jang, D.J., Medina, B.M., Gierschner,
J., Soo, Y.P.: A white-light-emitting molecule: frustrated energy transfer between constituent
emitting centers. J. Am. Chem. Soc. 131, 14043–14049 (2009)
65. Kim, S., Seo, J., Jung, H.K., Kim, J.-J., Park, S.Y.: White luminescence from polymer thin
films containing excited-state intramolecular proton-transfer dyes. Adv. Mater. 17, 2077–2082
(2005)
66. Chang, S.M., Tzeng, Y.J., Wu, S.Y., Li, K.Y., Hsueh, K.L.: Emission of white light from 2-(2 -
hydroxyphenyl) benzothiazole in polymer electroluminescent devices. Thin Solid Films 477,
38–41 (2005)
67. Shono, H., Ohkawa, T., Tomoda, H., Mutai, T., Araki, K.: Fabrication of colorless organic
materials exhibiting white luminescence using normal and excited-state intramolecular proton
transfer processes. ACS Appl. Mater. Interfaces. 3, 654–657 (2011)
68. Tang, K.-C., Chang, M.-J., Lin, T.-Y., Pan, H.-A., Fang, T.-C., Chen, K.-Y., Hung, W.-Y., Hsu,
Y.-H., Chou, P.-T.: Fine tuning the energetics of excited-state intramolecular proton transfer
(ESIPT): white light generation in a single ESIPT system. J. Am. Chem. Soc. 133, 17738–17745
(2011)
69. Sun, W., Li, S., Hu, R., Qian, Y., Wang, S., Yang, G.: Understanding solvent effects on luminescent properties of a triple fluorescent ESIPT compound and application for white light
emission. J. Phys. Chem. A 113, 5888–5895 (2009)
70. Chen, K.-Y., Hsieh, C.-C., Cheng, Y.-M., Lai, C.-H., Chou, P.-T.: Extensive spectral tuning
of the proton transfer emission from 550 to 675 nm via a rational derivatization of
10-hydroxybenzo[h]quinoline. Chem. Commun. 4395–4397 (2006)
71. Douhal, A., Amat-Guerri, F., Acuna, A.U.: Photoinduced intramolecular proton transfer and
charge redistribution in imidazopyridines. J. Phys. Chem. 99, 76–80 (1995)
72. Douhal, A.: The involvement of rotational processes in the intramolecular proton-transfer cycle.
Ber. Bunsenges. Phys. Chem. 102, 448–451 (1998)
73. (a) Stasyuk, A.J., Banasiewicz, M., Cyra´ nski, M.K., Gryko, D.T.: Imidazo[1,2-a]pyridines
susceptible to excited state intramolecular proton transfer: one-pot synthesis via an OrtolevaKing reaction. J. Org. Chem. 77, 5552–5558 (2012)
74. Mutai, T., Sawatani, H., Shida, T., Shono, H., Araki, K.: Tuning of excited-state intramolecular
proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution
effect. J. Org. Chem. 78, 2482–2489 (2013)
75. Douhal, A., Amat-Guerri, F., Acuña, A.U.: Probing nanocavities with proton-transfer fluorescence. Angew. Chemie Int. Ed. Eng. 36, 1514–1516 (1997)
76. (a) Crystallographic data for 1-BG: C 13 H 10 N 2 O, FW = 210.23, Orthorhombic, Pbca, a =
7.6560(2), b = 12.1630(3), c = 22.2380(5) Å, V = 2070.80(9) Å 3 , Z = 8, d calcd = 1.349, T =
298(2) K, 18651 measured and 2030 independent reflections, R 1 = 0.0548, wR 2 = 0.1297, GOF
= 1.104. CCDC No.: 698144 (b) crystallographic data for 1-Y: C 13 H 10 N 2 O, FW = 210.23,
Monoclinic, P2 1 /c, a = 18.2400(4), b = 5.77300(10), c = 20.3010(5) Å, b = 108.1650(10)°, V
= 2031.15(8) Å 3 , Z = 8, d calcd = 1.375, T = 298(2) K, 18482 measured and 3733 independent
reflections, R 1 = 0.0624, wR 2 = 0.1732, GOF = 1.116. CCDC No.: 698145
77. Khan, A.U., Kasha, M.: Mechanism of four-level laser action in solution excimer and excitedstate proton-transfer cases. Proc. Natl. Acad. Sci. U. S. A. 80, 1767–1770 (1983)
78. Shigemitsu, Y., Mutai, T., Houjou, H., Araki, K.: Excited-state intramolecular proton transfer
(ESIPT) emission of hydroxyphenylimidazopyridine: computational study on enhanced and
polymorph-dependent luminescence in the solid state. J. Phys. Chem. A 116, 12041–12048
(2012)
T. Mutai
62. Park, S., Park, J., Seo, S.H., Kim, S.Y.: Park, tetraphenylimidazole-based excited-state
intramolecular proton-transfer molecules for highly efficient blue electroluminescence. Adv.
Funct. Mater. 18, 726–731 (2008)
63. Hu, Y., Zhang, Y., Liang, F., Wang, L., Ma, D., Jing, X.: Blue organic light-emitting diodes
based on an oxadiazole-containing organic molecule exhibiting excited state intramolecular
proton transfer. Synth. Met. 137, 1123–1124 (2003)
64. Park, S., Ji, E.K., Se, H.K., Seo, J., Chung, K., Park, S.Y., Jang, D.J., Medina, B.M., Gierschner,
J., Soo, Y.P.: A white-light-emitting molecule: frustrated energy transfer between constituent
emitting centers. J. Am. Chem. Soc. 131, 14043–14049 (2009)
65. Kim, S., Seo, J., Jung, H.K., Kim, J.-J., Park, S.Y.: White luminescence from polymer thin
films containing excited-state intramolecular proton-transfer dyes. Adv. Mater. 17, 2077–2082
(2005)
66. Chang, S.M., Tzeng, Y.J., Wu, S.Y., Li, K.Y., Hsueh, K.L.: Emission of white light from 2-(2 -
hydroxyphenyl) benzothiazole in polymer electroluminescent devices. Thin Solid Films 477,
38–41 (2005)
67. Shono, H., Ohkawa, T., Tomoda, H., Mutai, T., Araki, K.: Fabrication of colorless organic
materials exhibiting white luminescence using normal and excited-state intramolecular proton
transfer processes. ACS Appl. Mater. Interfaces. 3, 654–657 (2011)
68. Tang, K.-C., Chang, M.-J., Lin, T.-Y., Pan, H.-A., Fang, T.-C., Chen, K.-Y., Hung, W.-Y., Hsu,
Y.-H., Chou, P.-T.: Fine tuning the energetics of excited-state intramolecular proton transfer
(ESIPT): white light generation in a single ESIPT system. J. Am. Chem. Soc. 133, 17738–17745
(2011)
69. Sun, W., Li, S., Hu, R., Qian, Y., Wang, S., Yang, G.: Understanding solvent effects on luminescent properties of a triple fluorescent ESIPT compound and application for white light
emission. J. Phys. Chem. A 113, 5888–5895 (2009)
70. Chen, K.-Y., Hsieh, C.-C., Cheng, Y.-M., Lai, C.-H., Chou, P.-T.: Extensive spectral tuning
of the proton transfer emission from 550 to 675 nm via a rational derivatization of
10-hydroxybenzo[h]quinoline. Chem. Commun. 4395–4397 (2006)
71. Douhal, A., Amat-Guerri, F., Acuna, A.U.: Photoinduced intramolecular proton transfer and
charge redistribution in imidazopyridines. J. Phys. Chem. 99, 76–80 (1995)
72. Douhal, A.: The involvement of rotational processes in the intramolecular proton-transfer cycle.
Ber. Bunsenges. Phys. Chem. 102, 448–451 (1998)
73. (a) Stasyuk, A.J., Banasiewicz, M., Cyra´ nski, M.K., Gryko, D.T.: Imidazo[1,2-a]pyridines
susceptible to excited state intramolecular proton transfer: one-pot synthesis via an OrtolevaKing reaction. J. Org. Chem. 77, 5552–5558 (2012)
74. Mutai, T., Sawatani, H., Shida, T., Shono, H., Araki, K.: Tuning of excited-state intramolecular
proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution
effect. J. Org. Chem. 78, 2482–2489 (2013)
75. Douhal, A., Amat-Guerri, F., Acuña, A.U.: Probing nanocavities with proton-transfer fluorescence. Angew. Chemie Int. Ed. Eng. 36, 1514–1516 (1997)
76. (a) Crystallographic data for 1-BG: C 13 H 10 N 2 O, FW = 210.23, Orthorhombic, Pbca, a =
7.6560(2), b = 12.1630(3), c = 22.2380(5) Å, V = 2070.80(9) Å 3 , Z = 8, d calcd = 1.349, T =
298(2) K, 18651 measured and 2030 independent reflections, R 1 = 0.0548, wR 2 = 0.1297, GOF
= 1.104. CCDC No.: 698144 (b) crystallographic data for 1-Y: C 13 H 10 N 2 O, FW = 210.23,
Monoclinic, P2 1 /c, a = 18.2400(4), b = 5.77300(10), c = 20.3010(5) Å, b = 108.1650(10)°, V
= 2031.15(8) Å 3 , Z = 8, d calcd = 1.375, T = 298(2) K, 18482 measured and 3733 independent
reflections, R 1 = 0.0624, wR 2 = 0.1732, GOF = 1.116. CCDC No.: 698145
77. Khan, A.U., Kasha, M.: Mechanism of four-level laser action in solution excimer and excitedstate proton-transfer cases. Proc. Natl. Acad. Sci. U. S. A. 80, 1767–1770 (1983)
78. Shigemitsu, Y., Mutai, T., Houjou, H., Araki, K.: Excited-state intramolecular proton transfer
(ESIPT) emission of hydroxyphenylimidazopyridine: computational study on enhanced and
polymorph-dependent luminescence in the solid state. J. Phys. Chem. A 116, 12041–12048
(2012)