14 Luminescent Crystal–Control of Excited-State …
297
79. Guallar, V., Moreno, M., Lluch, J.M., Amat-Guerri, F., Douhal, A.: H-atom transfer and
rotational processes in the ground and first singlet excited electronic states of 2-(2 -
Hydroxyphenyl)oxazole derivatives: experimental and theoretical studies. J. Phys. Chem. 100,
19789–19794 (1996)
80. Organero, J.A., Moreno, M., Santos, L., Lluch, J.M., Douhal, A.: Photoinduced proton transfer
and rotational motion of 1-Hydroxy-2-acetonaphthone in the S 1 state: a theoretical insight into
its photophysics. J. Phys. Chem. A 104, 8424–8431 (2000)
81. Fournier, T., Pommeret, S., Mialocq, J.-C., Deflandre, A.: Excited-state intramolecular proton
transfer (ESIPT) and energy relaxation processes in hydroxyphenylbenzotriazole derivatives: a femtosecond laser study. In: De Schryver, F.C., De Feyter, S., Schweitzer, G. (eds.)
Femtochemistry, pp. 323–333. Wiley-VCH, Weinheim, Germany (2001)
82. de Klerk, J.S., Bader, A.N., Ariese, F., Gooijer, C.: High-resolution fluorescence studies on
excited-state intra- and intermolecular proton transfer. In: Geddes, C.D. (ed.) Reviews in
Fluorescence, pp. 271–298. Springer, New York (2009)
83. Mitra, S., Tamai, N.: A combined experimental and theoretical study on the photochromism of
aromatic anils. Chem. Phys. 246, 463–475 (1999)
84. (a) Gentili, P.L., Ortica, F., Romani, A., Favaro, G.: Effects of proximity on the relaxation
dynamics of flindersine and 6(5H)-Phenanthridinone. J. Phys. Chem. A 111, 193–200 (2007);
(b) Domcke, W., Yarkony, D.R., Köppel, H.: Conical Intersections: Electronic Structure,
Dynamics & Spectroscopy, Advanced Series in Physical Chemistry. World Scientific, Singapore (2004); (c) Gustavsson, T., Improta, R., Markovitsi, D.: DNA/RNA: building blocks of
life under UV irradiation. J. Phys. Chem. Lett. 1, 2025–2030 (2010)
85. (a) Merchán, M., Serrano-Andrés, L.: Ultrafast internal conversion of excited cytosine via the
lowest ππ* electronic singlet state. J. Am. Chem. Soc. 125, 8108–8109 (2003); (b) Ismail, N.,
Blancafort, L., Olivucci, M., Kohler, B., Robb, M.A.: Ultrafast decay of electronically excited
singlet cytosine via a π,π* to n 0 ,π* state switch. J. Am. Chem. Soc. 124, 6818–6819 (2002); (c)
Blancafort, L., Cohen, B., Hare, P.M., Kohler, B., Robb, M.A.: Singlet excited-state dynamics
of 5-Fluorocytosine and cytosine: an experimental and computational study. J. Phys. Chem.
A 109, 4431–4436 (2005); (d) Zgierski, M.Z., Fujiwara, T., Kofron, W.G., Lim, E.C.: Highly
effective quenching of the ultrafast radiationless decay of photoexcited pyrimidine bases by
covalent modification: photophysics of 5,6-trimethylenecytosine and 5,6-trimethyleneuracil.
Phys. Chem. Chem. Phys. 9, 3206–3209 (2007); (e) Paterson, M.J., Robb, M.A., Blancafort,
L., DeBellis, A.D.: Theoretical study of benzotriazole uv photostability: ultrafast deactivation
through coupled proton and electron transfer triggered by a charge-transfer state. J. Am. Chem.
Soc. 126, 2912–2922 (2004)
86. Fukunaga, H., Fedorov, D.G., Chiba, M., Nii, K., Kitaura, K.: Theoretical analysis of the
intermolecular interaction effects on the excitation energy of organic pigments: solid state
quinacridone. J. Phys. Chem. A 112, 10887–10894 (2008)
87. Filhol, J.-S., Deschamps, J., Dutremez, S.G., Boury, B., Barisien, T., Legrand, L., Schott, M.:
Polymorphs and colors of polydiacetylenes: a first principles study. J. Am. Chem. Soc. 131,
6976–6988 (2009)
88. Wu, Q., Peng, Q., Niu, Y., Gao, X., Shuai, Z.: Theoretical insights into the aggregation-induced
emission by hydrogen bonding: A QM/MM study. J. Phys. Chem. A 116, 3881–3888 (2012)
89. Mutai, T., Shono, H., Shigemitsu, Y., Araki, K.: Three-color polymorph-dependent luminescence: crystallographic analysis and theoretical study on excited-state intramolecular proton
transfer (ESIPT) luminescence of cyano-substituted imidazo[1,2-a]pyridine. CrystEngComm
16, 3890–3895 (2014)
90. Crystallographic data for 2-Y: C 14 H 9 N 3 O, FW = 235.24, Monoclinic, P2 1 /n, a = 6.052(6),
b = 4.919(5), c = 36.98(3) Å, β = 94.155(4)°, V = 1098.0(17) Å 3 , Z = 4, d calcd = 1.423, T
= 113(2) K, 8137 measured and 2402 independent reflections, R 1 = 0.0754, wR 2 = 0.2201,
GOF = 0.938. CCDC No.: 965203. Crystallographic data for 2-O: C 14 H 9 N 3 O, FW = 235.24,
Monoclinic, P2 1 /n, a = 13.654(6), b = 7.343(3), c = 14.200(6) Å, β = 130.054(2)°, V =
1089.8(8) Å 3 , Z = 4, d calcd = 1.434, T = 113(2) K, 8291 measured and 2487 independent
reflections, R 1 = 0.0334, wR 2 = 0.0963, GOF = 1.097. CCDC No.: 965204. Crystallographic
297
79. Guallar, V., Moreno, M., Lluch, J.M., Amat-Guerri, F., Douhal, A.: H-atom transfer and
rotational processes in the ground and first singlet excited electronic states of 2-(2 -
Hydroxyphenyl)oxazole derivatives: experimental and theoretical studies. J. Phys. Chem. 100,
19789–19794 (1996)
80. Organero, J.A., Moreno, M., Santos, L., Lluch, J.M., Douhal, A.: Photoinduced proton transfer
and rotational motion of 1-Hydroxy-2-acetonaphthone in the S 1 state: a theoretical insight into
its photophysics. J. Phys. Chem. A 104, 8424–8431 (2000)
81. Fournier, T., Pommeret, S., Mialocq, J.-C., Deflandre, A.: Excited-state intramolecular proton
transfer (ESIPT) and energy relaxation processes in hydroxyphenylbenzotriazole derivatives: a femtosecond laser study. In: De Schryver, F.C., De Feyter, S., Schweitzer, G. (eds.)
Femtochemistry, pp. 323–333. Wiley-VCH, Weinheim, Germany (2001)
82. de Klerk, J.S., Bader, A.N., Ariese, F., Gooijer, C.: High-resolution fluorescence studies on
excited-state intra- and intermolecular proton transfer. In: Geddes, C.D. (ed.) Reviews in
Fluorescence, pp. 271–298. Springer, New York (2009)
83. Mitra, S., Tamai, N.: A combined experimental and theoretical study on the photochromism of
aromatic anils. Chem. Phys. 246, 463–475 (1999)
84. (a) Gentili, P.L., Ortica, F., Romani, A., Favaro, G.: Effects of proximity on the relaxation
dynamics of flindersine and 6(5H)-Phenanthridinone. J. Phys. Chem. A 111, 193–200 (2007);
(b) Domcke, W., Yarkony, D.R., Köppel, H.: Conical Intersections: Electronic Structure,
Dynamics & Spectroscopy, Advanced Series in Physical Chemistry. World Scientific, Singapore (2004); (c) Gustavsson, T., Improta, R., Markovitsi, D.: DNA/RNA: building blocks of
life under UV irradiation. J. Phys. Chem. Lett. 1, 2025–2030 (2010)
85. (a) Merchán, M., Serrano-Andrés, L.: Ultrafast internal conversion of excited cytosine via the
lowest ππ* electronic singlet state. J. Am. Chem. Soc. 125, 8108–8109 (2003); (b) Ismail, N.,
Blancafort, L., Olivucci, M., Kohler, B., Robb, M.A.: Ultrafast decay of electronically excited
singlet cytosine via a π,π* to n 0 ,π* state switch. J. Am. Chem. Soc. 124, 6818–6819 (2002); (c)
Blancafort, L., Cohen, B., Hare, P.M., Kohler, B., Robb, M.A.: Singlet excited-state dynamics
of 5-Fluorocytosine and cytosine: an experimental and computational study. J. Phys. Chem.
A 109, 4431–4436 (2005); (d) Zgierski, M.Z., Fujiwara, T., Kofron, W.G., Lim, E.C.: Highly
effective quenching of the ultrafast radiationless decay of photoexcited pyrimidine bases by
covalent modification: photophysics of 5,6-trimethylenecytosine and 5,6-trimethyleneuracil.
Phys. Chem. Chem. Phys. 9, 3206–3209 (2007); (e) Paterson, M.J., Robb, M.A., Blancafort,
L., DeBellis, A.D.: Theoretical study of benzotriazole uv photostability: ultrafast deactivation
through coupled proton and electron transfer triggered by a charge-transfer state. J. Am. Chem.
Soc. 126, 2912–2922 (2004)
86. Fukunaga, H., Fedorov, D.G., Chiba, M., Nii, K., Kitaura, K.: Theoretical analysis of the
intermolecular interaction effects on the excitation energy of organic pigments: solid state
quinacridone. J. Phys. Chem. A 112, 10887–10894 (2008)
87. Filhol, J.-S., Deschamps, J., Dutremez, S.G., Boury, B., Barisien, T., Legrand, L., Schott, M.:
Polymorphs and colors of polydiacetylenes: a first principles study. J. Am. Chem. Soc. 131,
6976–6988 (2009)
88. Wu, Q., Peng, Q., Niu, Y., Gao, X., Shuai, Z.: Theoretical insights into the aggregation-induced
emission by hydrogen bonding: A QM/MM study. J. Phys. Chem. A 116, 3881–3888 (2012)
89. Mutai, T., Shono, H., Shigemitsu, Y., Araki, K.: Three-color polymorph-dependent luminescence: crystallographic analysis and theoretical study on excited-state intramolecular proton
transfer (ESIPT) luminescence of cyano-substituted imidazo[1,2-a]pyridine. CrystEngComm
16, 3890–3895 (2014)
90. Crystallographic data for 2-Y: C 14 H 9 N 3 O, FW = 235.24, Monoclinic, P2 1 /n, a = 6.052(6),
b = 4.919(5), c = 36.98(3) Å, β = 94.155(4)°, V = 1098.0(17) Å 3 , Z = 4, d calcd = 1.423, T
= 113(2) K, 8137 measured and 2402 independent reflections, R 1 = 0.0754, wR 2 = 0.2201,
GOF = 0.938. CCDC No.: 965203. Crystallographic data for 2-O: C 14 H 9 N 3 O, FW = 235.24,
Monoclinic, P2 1 /n, a = 13.654(6), b = 7.343(3), c = 14.200(6) Å, β = 130.054(2)°, V =
1089.8(8) Å 3 , Z = 4, d calcd = 1.434, T = 113(2) K, 8291 measured and 2487 independent
reflections, R 1 = 0.0334, wR 2 = 0.0963, GOF = 1.097. CCDC No.: 965204. Crystallographic