14 Luminescent Crystal–Control of Excited-State …
295
43. Ouyang, J., Ouyang, C., Fujii, Y., Nakano, Y., Shoda, T., Nagano, T.: Synthesis and fluorescent
properties of 2-(1H-benzimidazol-2-yl)-phenol derivatives. J. Heterocycl. Chem. 41, 359–365
(2004)
44. Das, K., Sarkar, N., Majumdar, D., Bhattacharyya, K.: Excited-state intramolecular proton
transfer and rotamerism of 2-(2 -hydroxyphenyl) benzimidazole. Chem. Phys. Lett. 198, 443–
448 (1992)
45. Seo, J., Kim, S., Park, S., Park, S.Y.: Tailoring the excited-state intramolecular proton transfer
(ESIPT) fluorescence of 2-(2 -Hydroxyphenyl)benzoxazole derivatives. Bull. Korean Chem.
Soc. 26, 1706–1710 (2005)
46. Chen, W., Twum, E.B., Li, L., Wright, B.D., Rinaldi, P.L., Pang, Y.: Rotational energy barrier
of 2-(2 ,6 -Dihydroxyphenyl)benzoxazole: a case study by NMR. J. Org. Chem. 77, 285–290
(2012)
47. Ohshima, A., Momotake, A., Nagahata, R., Arai, T.: Enhancement of the large stokes-shifted
fluorescence emission from the 2-(2 -hydroxyphenyl)benzoxazole core in a dendrimer. J. Phys.
Chem. A 109, 9731–9736 (2005)
48. Wang, H., Zhang, H., Abou-Zied, O.K., Yu, C., Romesberg, F.E., Glasbeek, M.: Femtosecond
fluorescence upconversion studies of excited-state proton-transfer dynamics in 2-(2 -
hydroxyphenyl)benzoxazole (HBO) in liquid solution and DNA. Chem. Phys. Lett. 367,
599–608 (2003)
49. Ma, J., Zhao, J., Yang, P., Huang, D., Zhang, C., Li, Q.: New excited state intramolecular
proton transfer (ESIPT) dyes based on naphthalimide and observation of long-lived triplet
excited states. Chem. Commun. 48, 9720–9722 (2012)
50. Yao, D., Zhao, S., Guo, J., Zhang, Z., Zhang, H., Liu, Y., Wang, Y.: Hydroxyphenylbenzothiazole based full color organic emitting materials generated by facile molecular
modification. J. Mater. Chem. 21, 3568–3570 (2011)
51. Mohammed, O.F., Luber, S., Batista, V.S., Nibbering, E.T.J.: Ultrafast branching of reaction
pathways in 2-(2 -Hydroxyphenyl)benzothiazole in polar acetonitrile solution. J. Phys. Chem.
A 115, 7550–7558 (2011)
52. Rini, M., Dreyer, J., Nibbering, E.T.J., Elsaesser, T.: Ultrafast vibrational relaxation processes
induced by intramolecular excited state hydrogen transfer. Chem. Phys. Lett. 374, 13–19 (2003)
53. Frey, F., Laermer, T.: Elsaesser, Femtosecond studies of excited-state proton and deuterium
transfer in benzothiazole compounds. J. Phys. Chem. 95, 10391–10395 (1991)
54. Anthony, K., Brown, R.G., Hepworth, J.D., Hodgson, K.W., May, B., West, M.A.: Solid-state
fluorescent photophysics of some 2-substituted benzothiazoles. J. Chem. Soc. Perkin Trans. 2,
2111–2117 (1984)
55. Amimoto, K., Kawato, T.: Photochromism of organic compounds in the crystal state. J.
Photochem. Photobiol. C Photochem. Rev. 6, 207–226 (2005)
56. Mitra, S., Tamai, N.: Dynamics of photochromism in salicylideneaniline: a femtosecond
spectroscopic study. Phys. Chem. Chem. Phys. 5, 4647–4652 (2003)
57. Harada, J., Fujiwara, T., Ogawa, K.: Crucial role of fluorescence in the solid-state thermochromism of salicylideneanilines. J. Am. Chem. Soc. 129, 16216–16221 (2007)
58. Kwon, J.E., Park, S.Y.: Advanced organic optoelectronic materials: harnessing excited-state
intramolecular proton transfer (ESIPT) process. Adv. Mater. 23, 3615–3642 (2011)
59. Seo, J., Kim, S., Lee, Y.S., Kwon, O.H., Park, K.H., Choi, S.Y., Chung, Y.K., Jang, D.J.,
Park, S.Y.: Enhanced solid-state fluorescence in the oxadiazole-based excited-state intramolecular proton-transfer (ESIPT) material: synthesis, optical property, and crystal structure. J.
Photochem. Photobiol. A Chem. 191, 51–58 (2007)
60. Chuang, W.-T., Hsieh, C.-C., Lai, C.-H., Lai, C.-H., Shih, C.-W., Chen, K.-Y., Hung, W.-Y., Hsu,
Y.-H., Chou, P.-T.: Excited-state intramolecular proton transfer molecules bearing o-hydroxy
analogues of green fluorescent protein chromophore. J. Org. Chem. 76, 8189–8202 (2011)
61. Mutai, T., Tomoda, H., Ohkawa, T., Yabe, Y., Araki, K.: Switching of polymorph-dependent
ESIPT luminescence of an imidazo[1,2-a]pyridine derivative. Angew. Chem. Int. Ed. 47, 9522–
9524 (2008)
295
43. Ouyang, J., Ouyang, C., Fujii, Y., Nakano, Y., Shoda, T., Nagano, T.: Synthesis and fluorescent
properties of 2-(1H-benzimidazol-2-yl)-phenol derivatives. J. Heterocycl. Chem. 41, 359–365
(2004)
44. Das, K., Sarkar, N., Majumdar, D., Bhattacharyya, K.: Excited-state intramolecular proton
transfer and rotamerism of 2-(2 -hydroxyphenyl) benzimidazole. Chem. Phys. Lett. 198, 443–
448 (1992)
45. Seo, J., Kim, S., Park, S., Park, S.Y.: Tailoring the excited-state intramolecular proton transfer
(ESIPT) fluorescence of 2-(2 -Hydroxyphenyl)benzoxazole derivatives. Bull. Korean Chem.
Soc. 26, 1706–1710 (2005)
46. Chen, W., Twum, E.B., Li, L., Wright, B.D., Rinaldi, P.L., Pang, Y.: Rotational energy barrier
of 2-(2 ,6 -Dihydroxyphenyl)benzoxazole: a case study by NMR. J. Org. Chem. 77, 285–290
(2012)
47. Ohshima, A., Momotake, A., Nagahata, R., Arai, T.: Enhancement of the large stokes-shifted
fluorescence emission from the 2-(2 -hydroxyphenyl)benzoxazole core in a dendrimer. J. Phys.
Chem. A 109, 9731–9736 (2005)
48. Wang, H., Zhang, H., Abou-Zied, O.K., Yu, C., Romesberg, F.E., Glasbeek, M.: Femtosecond
fluorescence upconversion studies of excited-state proton-transfer dynamics in 2-(2 -
hydroxyphenyl)benzoxazole (HBO) in liquid solution and DNA. Chem. Phys. Lett. 367,
599–608 (2003)
49. Ma, J., Zhao, J., Yang, P., Huang, D., Zhang, C., Li, Q.: New excited state intramolecular
proton transfer (ESIPT) dyes based on naphthalimide and observation of long-lived triplet
excited states. Chem. Commun. 48, 9720–9722 (2012)
50. Yao, D., Zhao, S., Guo, J., Zhang, Z., Zhang, H., Liu, Y., Wang, Y.: Hydroxyphenylbenzothiazole based full color organic emitting materials generated by facile molecular
modification. J. Mater. Chem. 21, 3568–3570 (2011)
51. Mohammed, O.F., Luber, S., Batista, V.S., Nibbering, E.T.J.: Ultrafast branching of reaction
pathways in 2-(2 -Hydroxyphenyl)benzothiazole in polar acetonitrile solution. J. Phys. Chem.
A 115, 7550–7558 (2011)
52. Rini, M., Dreyer, J., Nibbering, E.T.J., Elsaesser, T.: Ultrafast vibrational relaxation processes
induced by intramolecular excited state hydrogen transfer. Chem. Phys. Lett. 374, 13–19 (2003)
53. Frey, F., Laermer, T.: Elsaesser, Femtosecond studies of excited-state proton and deuterium
transfer in benzothiazole compounds. J. Phys. Chem. 95, 10391–10395 (1991)
54. Anthony, K., Brown, R.G., Hepworth, J.D., Hodgson, K.W., May, B., West, M.A.: Solid-state
fluorescent photophysics of some 2-substituted benzothiazoles. J. Chem. Soc. Perkin Trans. 2,
2111–2117 (1984)
55. Amimoto, K., Kawato, T.: Photochromism of organic compounds in the crystal state. J.
Photochem. Photobiol. C Photochem. Rev. 6, 207–226 (2005)
56. Mitra, S., Tamai, N.: Dynamics of photochromism in salicylideneaniline: a femtosecond
spectroscopic study. Phys. Chem. Chem. Phys. 5, 4647–4652 (2003)
57. Harada, J., Fujiwara, T., Ogawa, K.: Crucial role of fluorescence in the solid-state thermochromism of salicylideneanilines. J. Am. Chem. Soc. 129, 16216–16221 (2007)
58. Kwon, J.E., Park, S.Y.: Advanced organic optoelectronic materials: harnessing excited-state
intramolecular proton transfer (ESIPT) process. Adv. Mater. 23, 3615–3642 (2011)
59. Seo, J., Kim, S., Lee, Y.S., Kwon, O.H., Park, K.H., Choi, S.Y., Chung, Y.K., Jang, D.J.,
Park, S.Y.: Enhanced solid-state fluorescence in the oxadiazole-based excited-state intramolecular proton-transfer (ESIPT) material: synthesis, optical property, and crystal structure. J.
Photochem. Photobiol. A Chem. 191, 51–58 (2007)
60. Chuang, W.-T., Hsieh, C.-C., Lai, C.-H., Lai, C.-H., Shih, C.-W., Chen, K.-Y., Hung, W.-Y., Hsu,
Y.-H., Chou, P.-T.: Excited-state intramolecular proton transfer molecules bearing o-hydroxy
analogues of green fluorescent protein chromophore. J. Org. Chem. 76, 8189–8202 (2011)
61. Mutai, T., Tomoda, H., Ohkawa, T., Yabe, Y., Araki, K.: Switching of polymorph-dependent
ESIPT luminescence of an imidazo[1,2-a]pyridine derivative. Angew. Chem. Int. Ed. 47, 9522–
9524 (2008)