The Journal of Organic Chemistry
ARTICLE
of upconversion, transient absorption, calculation information,
77 K emission spectra, and photostability of the sensitizers and
photophysics of the acceptors. This material is available free of
(13) Singh-Rachford, T. N.; Castellano, F. N. Inorg. Chem. 2009,
48, 2541–2548.
(14) Singh-Rachford, T. N.; Castellano, F. N. J. Phys. Chem. A 2008,
112, 3550–3556.
(15) Wolfbeis, O.; Narayanaswamy, R. Optical Sensors: Industrial,
Environmental and Diagnostic Applications; Springer-Verlag: Berlin,
Heidelberg, 2004.
’ AUTHOR INFORMATION
(16) Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2nd ed.;
Kluwer Academic: New York, 1999.
(17) Yogo, T.; Urano, Y.; Ishitsuka, Y.; Maniwa, F.; Nagano, T. J. Am.
Chem. Soc. 2005, 127, 12162–12163.
Corresponding Author
*E-mail: zhaojzh@dlut.edu.cn.
(18) Gorman, A.; Killoran, J.; O’Shea, C.; Kenna, T.; Gallagher,
W. M.; O’Shea, D. F. J. Am. Chem. Soc. 2004, 126, 10619–10631.
(19) (a) Ulrich, G.; Ziessel, R.; Harriman, A. Angew. Chem., Int. Ed.
2008, 47, 1184–1201. (b) Zhang, X.; Xiao, Y.; Qian, X. Angew. Chem.,
Int. Ed. 2008, 47, 8025–8029. (c) Peng, X.; Du, J.; Fan, J.; Wang, J.;
Wu, Y.; Zhao, J.; Sun, S.; Xu., T. J. Am. Chem. Soc. 2007, 129, 1500–1501.
(d) Ziessel, R.; Harriman, A. Chem. Commun. 2011, 47, 611–631.
(e) Guliyev, R.; Coskun, A.; Akkaya., E. U. J. Am. Chem. Soc. 2009,
131, 9007–9013.
’ ACKNOWLEDGMENT
We thank the NSFC (20972024 and 21073028), Fundamen-
tal Research Funds for the Central Universities (DUT10ZD212
and DUT11LK19), Royal Society (U.K.) and NSFC (China-
U.K. Cost-Share program/21011130154), Ministry of Education
(SRF for ROCS, SRFDP-200801410004 and NCET-08-0077),
State Key Laboratory of Fine Chemicals (KF0802), and the
Education Department of Liaoning Province (2009T015) for
financial support.
(20) Lee, J. S.; Kang, N. Y.; Kim, Y. K.; Samanta, A.; Feng, S.; Kim,
H. K.; Vendrell, M.; Park, J. H.; Chang, Y. T. J. Am. Chem. Soc. 2009,
131, 10077–10082.
(21) Singh-Rachford, T. N.; Haefele, A.; Ziessel, R.; Castellano, F. N.
J. Am. Chem. Soc. 2008, 130, 16164–16165.
’ REFERENCES
(22) (a) Baruah, M.; Qin, W.; Flors, C.; Hofkens, J.; Vallꢀee, R. A. L.;
Beljonne, D.; der Auweraer, M. V.; De Borggraeve, W. M.; Boens, N.
J. Phys. Chem. A 2006, 110, 5998–6009.(b) Turro, N. J.; Ramamurthy,
V.; Scaiano, J. C. Principles of Molecular Photochemistry: An Introduction;
University Science Books: Sausalito, CA, 2009. (c) Immitzer, B.; Falk, H.
Monatsh. Chem. 2000, 131, 1167–1171.
(23) Galletta, M.; Campagna, S.; Quesada, M.; Ulrich, G.; Ziessel, R.
Chem. Commun. 2005, 4222–4224.
(24) Rachford, A. A.; Ziessel, R.; Bura, T.; Retailleau, P.; Castellano,
F. N. Inorg. Chem. 2010, 49, 3730–3736.
(25) (a) Galletta, M.; Puntoriero, F.; Campagna, S.; Chiorboli, C.;
Quesada, M.; Goeb, S.; Ziessel, R. J. Phys. Chem. A 2006,
110, 4348–4358.
(26) Singh-Rachford, T. N.; Castellano, F. N. J. Phys. Chem. A 2009,
113, 5912–5917.
(27) Chen, H. C.; Hung, C. Y.; Wang, K. H.; Chen, H. L.; Fann,
W. S.; Chien, F. C.; Chen, P.; Chow, T. J.; Hsu, C. P.; Sun, S. S. Chem.
Commun. 2009, 4064–4066.
(28) Cheng, Y. Y.; Khoury, T.; Clady, R. G. C. R.; Tayebjee, M. J. Y.;
Ekins-Daukes, N. J.; Crossleya, M. J.; Schmidt, T. W. Phys. Chem. Chem.
Phys. 2010, 12, 66–71.
(1) Baluschev, S.; Yakutkin, V.; Miteva, T.; Avlasevich, Y.; Chernov,
S.; Aleshchenkov, S.; Nelles, G.; Cheprakov, A.; Yasuda, A.; M€ullen, K.;
Wegner, G. Angew. Chem., Int. Ed. 2007, 46, 7693–7696.
(2) Warther, D.; Bolze, F.; Lꢀeonard, J.; Gug, S.; Specht, A.; Puliti, D.;
Sun, X. H.; Kessler, P.; Lutz, Y.; Vonesch, J. L.; Winsor, B.; Nicoud, J. F.;
Goeldner, M. J. Am. Chem. Soc. 2010, 132, 2585–2590.
(3) Zhang, P.; Wang, M.; Dong, J.; Li, X.; Wang, F.; Wu, L.; Sun, L.
J. Phys. Chem. C 2010, 114, 15868–15874.
(4) Kim, H. M.; Cho, B. R. Acc. Chem. Res. 2009, 42, 863–872.
(5) Kim, M. K.; Lim, C. S.; Hong, J. T.; Han, J. H.; Jang, H. Y.; Kim,
H. M.; Cho, B. R. Angew. Chem., Int. Ed. 2010, 49, 364–367.
(6) Kushwaha, S. K.; Shakir, M.; Maurya, K. K.; Shah, A. L.; Wahab,
M. A.; Bhagavannarayana, G. J. Appl. Phys. 2010, 108, 033506/1–033506/7.
(7) Tian, H.; Jiang, X.; Yu, Z.; Kloo, L.; Hagfeldt, A.; Sun, L. Angew.
Chem. 2010, 122, 7486–7489; Angew. Chem., Int. Ed. 201049, 7328ꢀ
7331.
(8) Matsunami, M.; Chainani, A.; Taguchi, M.; Eguchi, R.; Ishida, Y.;
Takata, Y.; Okamura, H.; Nanba, T.; Yabashi, M.; Tamasaku, K.;
Nishino, Y.; Ishikawa, T.; Senba, Y.; Ohashi, H.; Tsujii, N.; Ochiai, A.;
Shin, S. Phys. Rev. B 2008, 78, 195112/1–195112/5.
(9) (a) Parker, C. A.; hatchard, C. G.; Joyce, T. A. Nature 1965,
205, 1282–1284. (b) Monguzzi, A.; Tubino, R.; Meinardi, F. Phys. Rev. B
2008, 77, 155122/1–155122/4.
(10) (a) Islangulov, R. R.; Kozlov, D. V.; Castellano, F. N. Chem.
Commun. 2005, 3776–3778. (b) Singh-Rachford, T. N.; Islangulov,
R. R.; Castellano, F. N. J. Phys. Chem. A 2008, 112, 3906–3910. (c)
Singh- Rachford, T. N.; Castellano, F. N. Coord. Chem. Rev. 2010,
254, 2560–2573. (d) Islangulov, R. R.; Lott, J.; Weder, C.; Castellano.,
F. N. J. Am. Chem. Soc. 2007, 129, 12652–12653.
(29) Du, P.; Eisenberg, R. Chem. Sci. 2010, 1, 502–506.
(30) Zhao, W.; Castellano, F. N. J. Phys. Chem. A 2006, 110,
11440–11445.
(31) Zhang, D.; Wang, Y.; Xiao, Y.; Qian, S.; Qian, X. Tetrahedron
2009, 65, 8099–8013.
(32) Frisch, M. J. et al. Gaussian 09 Revision A.1; Gaussian Inc.:
Wallingford, CT, 2009.
(11) (a) Singh-Rachford, T. N.; Castellano, F. N. J. Phys. Chem. Lett.
2010, 1, 195–200. (b) Cheng, Y. Y.; F€uckel, B.; Khoury, T.; Clady, R. G.
C. R.; Tayebjee, M. J. Y.; Ekins-Daukes, N. J.; Crossley, M. J.; Schmidt,
T. W. J. Phys. Chem. Lett. 2010, 1, 1795–1799.
(12) (a) Kozlov, D. V.; Castellano, F. N. Chem. Commun.
2004, 2860–2861. (b) Ji, S.; Wu, W.; Wu, W.; Guo, H.; Zhao, J. Angew.
Chem., Int. Ed. 2011, 50, 1626–1629.(c) Ji, S.; Guo, H.; Wu, W.; Wu, W.
Zhao, J. Angew. Chem., Int. Ed. 2011; Epub ahead of print, DOI:
10.1002/anie.201008134. (d) Wu, W.; Wu, W.; Ji, S.; Guo, H.; Zhao,
J. Dalton Trans. 2011, 40, 5953–5963.(d) Liu, Y.; Wu, W.; Zhang, X.;
Guo, H.; Zhao, J. Dalton Trans. 2011; Epub ahead of print, DOI:
10.1039/c1dt10679a. (e) Sun, H.; Guo, H.; Wu, W.; Liu, X.; Zhao, J.
Dalton Trans. 2011, 40, 7834ꢀ7841. (f) Sun, J.; Wu, W.; Guo, H.; Zhao,
J. Eur. J. Inorg. Chem. 2011, 3165ꢀ3173.
7064
dx.doi.org/10.1021/jo200990y |J. Org. Chem. 2011, 76, 7056–7064