Journal of the American Chemical Society
ARTICLE
fluorescent compounds can be accessed using the Seoul-Fluor
core skeleton with minimal structural perturbation.
(c) Grimsdale, A. C.; Chan, K. L.; Martin, R. E.; Jokisz, P. G.; Holmes,
A. B. Chem. Rev. 2009, 109, 897–1091.
(5) Kim, E.; Park, S. B. Chem.—Asian J. 2009, 4, 1646–1658 and
references therein.
Seoul-Fluor is a novel organic fluorophore with tunable
emission wavelength covering the full range of visible color,
which is particularly important from the perspective of multi-
plexing capability. In addition, a rational design, guided by
systematic analysis, theoretical computation, and known numer-
ical values, is possible with accurate and practical predictability;
fluorescent compounds with desired photophysical properties
can be acquired without the need for a tiresome synthesis and
trial-and-error process. Therefore, this study revealed that we
discovered a new fluorescent core skeleton, Seoul-Fluor, with
full-color tunability and accurate predictability. Considering that
the prediction of the emission wavelength of given fluorescent
compounds is still rare and highly difficult, this remarkable result
clearly shows how a combinatorial approach and systematic
analysis can help us address these unsolved problems using a
rational design-based approach and was exemplified with the
development of novel organic fluorophores. With its unique
properties, we hope that Seoul-Fluor can function as a versatile
palette for developing desired fluorescent probes.
(6) Lavis, L. D.; Raines, R. T. ACS Chem. Biol. 2008, 3, 142–155.
(7) Demchenko, A. P. Advanced Fluorescence Reporters in Chemistry
and Biology I; Springer-Verlag: Berlin, Heidelberg, 2010; Chapter 2.5,
pp 149ꢀ186.
(8) Bruchez, M.; Moronne, M.; Gin, P.; Weiss, S.; Alivisatos, A. P.
Science 1998, 281, 2013–2016.
(9) Murray, C. B.; Norris, D. J.; Bawendi, M. G. J. Am. Chem. Soc.
1993, 115, 8706–8715.
(10) Peng, Z. A.; Peng, X. J. Am. Chem. Soc. 2001, 123, 183–184.
(11) Peng, Z. A.; Peng, X. J. Am. Chem. Soc. 2002, 124, 3343–3353.
(12) Murray, C. B.; Kagan, C. R.; Bawendi, M. G. Annu. Rev. Mater.
Sci. 2000, 30, 545–610.
(13) Medintz, I. L.; Uyeda, H. T.; Goldman, E. R.; Mattoussi, H. Nat.
Mater. 2005, 4, 435–446.
(14) Michalet, X.; Pinaud, F. F.; Bentolila, L. A.; Tsay, J. M.; Doose,
S.; Li, J. J.; Sundaresan, G.; Wu, A. M.; Gambhir, S. S.; Weiss, S. Science
2005, 307, 538–544.
(15) Hardman, R. Environ. Health Perspect. 2006, 114, 165–172.
(16) Duncan, T. V.; Park, S.-J. J. Phys. Chem. B 2009, 113,
13216–13221.
(17) (a) Turro, M. J. Modern Molecular Photochemistry; University
Science Books: Sausolito, CA, 1991. (b) Yang, T.; Goddard, J. D. J. Phys.
Chem. A 2007, 111, 4489–4497.
(18) (a) Vendrell, M.; Lee, J.-S.; Chang, Y.-T. Curr. Opin. Chem. Biol.
2010, 14, 383–389. (b) Finney, N. S. Curr. Opin. Chem. Biol. 2006,
10, 238–245.
’ ASSOCIATED CONTENT
S
Supporting Information. Detailed synthetic procedures,
b
full characterization, and spectroscopic data of all new com-
pounds, procedure and data of the computational study, and
complete ref 3b. This material is available free of charge via the
(19) Schidel, M.-S.; Briehn, C. A.; Bau€erle, P. Angew. Chem., Int. Ed.
2001, 40, 4677–4680.
(20) (a) Sivakumar, K.; Xie, F.; Cash, B. M.; Long, S.; Barnhill, H. N.;
Wang, Q. Org. Lett. 2004, 6, 4603–4606. (b) Rosania, G. R.; Lee, J. W.;
Ding, L.; Yoon, H. S.; Chang, Y.-T. J. Am. Chem. Soc. 2003,
125, 1130–1131. (c) Ahn, Y. H.; Lee, J. S.; Chang, Y.-T. J. Am. Chem.
Soc. 2007, 129, 4510–4511. (d) Umezawa, K.; Nakamura, Y.; Makino,
H.; Citterio, D.; Suzuki, K. J. Am. Chem. Soc. 2008, 130, 1550–1551. (e)
Teo, Y. N.; Wilson, J. N.; Kool, E. T. J. Am. Chem. Soc. 2009, 131,
3923–3933.
’ AUTHOR INFORMATION
Corresponding Author
’ ACKNOWLEDGMENT
(21) Kim, E.; Koh, M.; Ryu, J.; Park, S. B. J. Am. Chem. Soc. 2008,
130, 12206–12207.
This study was supported by the National Research Founda-
tion of Korea (NRF) and the WCU program of the NRF funded
by the Korean Ministry of Education, Science, and Technology
(MEST). E.K., M.K., and B.J.L. are grateful for their predoctoral
fellowships, awarded by the BK21 Program.
(22) (a) Kim, J.; Song, H.; Park, S. B. Eur. J. Org. Chem.
2010, 3815–3822. (b) Oh, S.; Nam, H. J.; Park, J.; Beak, S. H.; Park,
S. B. ChemMedChem 2010, 5, 529–533. (c) Oh, S.; Jang, H. J.; Ko, S. K.;
K, Y.; Park, S. B. J. Comb. Chem. 2010, 12, 548–558. (d) Kim, Y.; Kim, J.;
Park, S. B. Org. Lett. 2009, 11, 17–20. (e) Park, S. O.; Kim, J.; Koh, M.;
Park, S. B. J. Comb. Chem. 2009, 11, 315–326. (f) Lee, S.; Park, S. B. Org.
Lett. 2009, 11, 5214–5217. (g) An, H.; Eum, S.-J.; Koh, M.; Lee, S. K.;
Park, S. B. J. Org. Chem. 2008, 73, 1752–1761. (h) Lee, S.-C.; Park, S. B.
Chem. Commun. 2007, 3714–3716. (i) Ko, S. K.; Jang, H. J.; Kim, E.;
Park, S. B. Chem. Commun. 2006, 28, 2962–2964.
(23) (a) Clusters and Nanomaterials; Kawazoe, Y., Ohno, K.,
Kondow, T., Eds.; Springer: New York, 2002. (b) Perdew, J. P.; Burke,
K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865–3868. (c) Perdew, J. P.;
Wang, Y. Phys. Rev. B 1996, 45, 13244–13249. (d) Kirkwood, J. C.;
Scheurer, C.; Chernyak, V.; Mukamel, J. J. Chem. Phys. 2001,
114, 2419–2429. (e) Tretiak, S.; Chernyak, V.; Mukamel, S. J. Phys.
Chem. B 1988, 102, 3310–3315. (f) Shimoi, Y.; Friedman, B. A. Chem.
Phys. 1999, 250, 13–22.
(24) Higashiguchi, K.; Matsuda, K.; Asano, Y.; Murakami, A.;
Nakamura, S.; Irie, M. Eur. J. Org. Chem. 2005, 91–97.
(25) Melhuish, W. H. J. Phys. Chem. 1960, 65, 229–230.
(26) Umberger, J. Q.; LaMer, V. K. J. Am. Chem. Soc. 1945,
67, 1099–1109.
(27) Magde, D.; Brannon, J. H.; Cremers, T. L.; Olmsted, J., III. J.
Phys. Chem. 1979, 83, 696–699.
(28) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165–195.
’ REFERENCES
(1) (a) Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3rd ed.;
Springer-Verlag: New York, 2006. (b) Rettig, W., Strehmel, B., Schrader,
S., Seifert, H., Eds. Applied Fluorescence in Chemistry, Biology, and
Medicine; Springer: New York, 1999.
(2) (a) Haugland, R. P. Handbook of Fluorescence Probes and Research
Products, 10th ed.; Molecular Probes: Eugene, OR, 2005. (b) Lavigne,
J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 2001, 40, 3118–3130. (c)
Zhang, J.; Campbell, R. E.; Ting, A. Y.; Tsien, R. Y. Nat. Rev. Mol. Cell.
Biol. 2002, 3, 906–918. (d) Domaille, D. W.; Que, E. L.; Chang, C. J. Nat.
Chem. Biol. 2008, 4, 168–175.
(3) (a) Goncalves, M. S. Chem. Rev. 2009, 109, 190–212. (b) Im, C.-N.
et al. Angew. Chem., Int. Ed. 2010, 49, 7497–7500. (c) Urano, Y.;
Asanuma, D.; Hama, Y.; Koyama, Y.; Barrett, T.; Kamiya, M.; Nagano,
T.; Watanabe, T.; Hasegawa, A.; Choyke, P. L.; Kobayashi, H. Nat. Med.
2009, 15, 104–109.
(4) (a) Tang, C. W.; Van Slyke, S. A. Appl. Phys. Lett. 1987,
51, 913–915. (b) Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burrouges,
J. H.; Marks, R. N.; Raliani, C.; Bradley, D. D. C.; Dos Santos, D. A.;
Brꢀedas, J. L.; L€ogdlund, M.; Salaneck, W. R. Nature 1999, 397, 121–128.
6648
dx.doi.org/10.1021/ja110766a |J. Am. Chem. Soc. 2011, 133, 6642–6649