Red-Emitting Carbopyronine Dyes
Shaker, Aachen, 1993; b) for the synthesis and properties of
red-emitting rhodamines with extended π-conjugation systems,
see: J. Liu, Z. Diwu, W.-Y. Leung, Y. Lu, B. Patch, R. P. Haug-
land, Tetrahedron Lett. 2003, 44, 4355–4359.
a) C. Aaron, C. C. Baker, J. Chem. Soc. B 1971, 319–324; b) J.
Frantzeskos, Dissertation (Neue langwellige Fluoresz-
enzfarbstoffe zur Markirung von Biomolekülen), Shaker Verlag
GmbH, Aachen, Germany, 2001; c) J. Arden-Jacob, J.
Frantzeskos, N. U. Kemnitzer, A. Zilles, K.-H. Drexhage, Spec-
trochim. Acta Sect. A 2001, 57, 2271–2283; d) R. O’Neill, P. V.
Fischer (Guava Tech. Inc.), WO 2004/003510 (08. Jan. 2004);
e) A. Zilles, J. Arden-Jacob, K.-H. Drexhage, N. U. Kemnitzer,
M. Hammers-Schneider (Atto-tec GmbH), WO 2005/003086
(13. Jan. 2005).
[1]
[2]
S. W. Hell, Far-Field Optical Nanoscopy, in: Single Molecule
Spectroscopy in Chemistry, Physics and Biology (Eds.: A. Graes-
lund, R. Rigler, J. Widengren), Springer, Berlin, 2009, pp. 365–
398.
[6]
For reviews, see: a) S. W. Hell, Science 2007, 316, 1153–1158;
b) M. Fernández-Suárez, A. Y. Ting, Nat. Rev. Mol. Cell Biol.
2008, 9, 929–943; c) D. Evanko, Nat. Methods 2009, 6, 19–20;
d) S. W. Hell, Nat. Methods 2009, 6, 24–32; e) X. Zhuang, Nat.
Photonics 2009, 3, 365–367; f) J. Lippincott-Schwartz, S. Man-
ley, Nat. Methods 2009, 6, 21–23; g) B. Huang, M. Bates, X.
Zhuang, Annu. Rev. Biochem. 2009, 78, 993–1016; for recent
reports, see: h) S. W. Hell, J. Wichmann, Opt. Lett. 1994, 19,
780–782; i) E. Betzig, G. H. Patterson, R. Sougrat, O. W. Lind-
wasser, S. Olenych, J. S. Bonifacino, M. W. Davidson, J. Lippin-
cott-Schwartz, H. F. Hess, Science 2006, 313, 1642–1645; j)
M. J. Rust, M. Bates, X. Zhuang, Nat. Methods 2006, 3, 793–
795; k) M. Bates, B. Huang, G. T. Dempsey, X. Zhuang, Sci-
ence 2007, 317, 1749–1753; l) S. T. Hess, T. P. K. Girirajan,
M. D. Mason, Biophys. J. 2006, 91, 4248–4272; m) J. Fölling,
V. Belov, R. Kunetsky, R. Medda, A. Schönle, A. Egner, C.
Eggeling, M. Bossi, S. W. Hell, Angew. Chem. 2007, 119, 6382–
6386; Angew. Chem. Int. Ed. 2007, 46, 6266–6270; n) J. Fölling,
V. Belov, D. Riedel, A. Schönle, A. Egner, C. Eggeling, M.
Bossi, S. W. Hell, ChemPhysChem 2008, 9, 321–326; o) M.
Bossi, J. Fölling, V. N. Belov, V. P. Boyarskiy, R. Medda, A.
Egner, C. Eggeling, A. Schönle, S. W. Hell, Nano Lett. 2008, 8,
2463–2468; p) V. P. Boyarskiy, V. N. Belov, R. Medda, B. Hein,
M. Bossi, S. W. Hell, Chem. Eur. J. 2008, 14, 1784–1792; q)
S. M. Polyakova, V. N. Belov, C. Eggeling, S. F. Yan, C. Ringe-
mann, G. Schwarzmann, A. de Meijere, S. W. Hell, Eur. J. Org.
Chem. 2009, 5162–5177; r) V. N. Belov, M. L. Bossi, J. Fölling,
V. P. Boyarskiy, S. W. Hell, Chem. Eur. J. 2009, 15, 10762–
10776; s) H. Schroff, C. G. Galbraith, J. A. Galbraith, H.
White, J. Gilette, S. Olenych, M. W. Davidson, E. Betzig, Proc.
Natl. Acad. Sci. USA 2007, 104, 20308–20313; t) M. Bates, B.
Huang, G. T. Dempsey, X. Zhuang, Science 2007, 317, 1749–
1753; u) B. Huang, W. Wang, M. Bates, X. Zhuang, Science
2008, 319, 810–813; v) B. Huang, S. A. Jones, B. Brandenburg,
X. Zhuang, Nat. Methods 2008, 5, 1047–1052.
[7]
[8]
J. Arden-Jacob, J. Frantzeskos, A. Zilles (K.-H. Drexhage), WO
00/64986 (02. Nov. 2000).
For a general description and spectral range of rhodamines as
fluorescent dyes, see: a) M. Beija, C. A. M. Afonso, J. M. G.
Martinho, Chem. Soc. Rev. 2009, 38, 2410–2433; b) M. S. T.
Gonçalves, Chem. Rev. 2009, 109, 190–212; c) R. P. Haugland,
A Guide to Fluorescent Probes and Labelling Technologies, Invi-
trogen, Carlsbad, 2005, pp. 11–37; d) for the use of rhodamines
in bioconjugation techniques, see: G. T. Hermanson, Biocon-
jugate Techniques, Academic Press, Amsterdam, 2008, pp. 415–
430; e) for laser dyes’ properties of rhodamines, see: F. P.
Schäfer, in: Dye Lasers; Topics in Applied Physics, v.1, (Ed.:
F. P. Schäfer), Springer, Berlin-Heidelberg, 1990, pp. 3–4; f) K.-
H. Drexhage, Dye Lasers; Topics in Applied Physics, v.1 (Ed.:
F. P. Schäfer), Springer, Berlin, Heidelberg, 1990, pp. 175–180;
g) K.-H. Drexhage, Top. Appl. Phys. 1973, 1, 155–200.
a) S. W. Hell, V. N. Belov, V. P. Boyarskiy, C. A. Wurm, S.
Jakobs, C. Geisler (Max Planck Innovation GmbH), PCT/EP/
2009/006578 (10.09.2009); b) V. N. Belov, V. P. Boyarskiy, C. A.
Wurm, S. Jakobs, S. W. Hell, Angew. Chem. 2010, 122, 3598–
3602; Angew. Chem. Int. Ed. 2010, 49, 3520–3523.
[9]
[10]
[11]
P. G. M. Wuts, Th. W. Green, Green’s Protective Groups in Or-
ganic Synthesis, John Wiley & Sons, New York, 2007, pp. 812–
818.
a) S. Ram, L. D. Spicer, Tetrahedron Lett. 1987, 28, 515–516;
b) T. Kiguchi, N. Kuninobu, Y. Takahashi, Y. Yoshida, T.
Naito, I. Ninomiya, Synthesis 1989, 778–781.
[3]
[4]
J. Fölling, M. Bossi, H. Bock, R. Medda, C. A. Wurm, B. Hein,
S. Jakobs, C. Eggeling, S. W. Hell, Nat. Methods 2008, 5, 943–
945.
[12]
[13]
J. F. Eggler, G. F. Holland, M. R. Johnson, R. A. Volkmann
(Pfizer Inc.) US Pat. 4738972 (19.04.1988).
a) K. Peneva, G. Mihov, F. Nolde, S. Rocha, J. Hotta, K.
Braeckmans, J. Hofkens, H. Uji-i, A. Hermann, K. Müllen,
Angew. Chem. 2008, 120, 3420–3423; Angew. Chem. Int. Ed.
2008, 47, 3372–3375; b) C. Jung, B. K. Müller, D. C. Lamb, F.
Nolde, K. Müllen, C. Bräuchle, J. Am. Chem. Soc. 2006, 128,
5283–5291; c) C. Jiao, K.-W. Huang, J. Luo, K. Zhang, C. Chi,
J. Wu, Org. Lett. 2009, 11, 4508–4511; d) J. Li, K. Zhang, X.
Zhang, K.-W. Huang, C. Chi, J. Wu, J. Org. Chem. 2010, 75,
856–863; e) S. L. Niu, G. Ulrich, R. Ziessel, A. Kiss, P.-Y. Re-
nard, A. Romieu, Org. Lett. 2009, 11, 2049–2052; for reviews
on BODIPY fluorescent dyes, see: f) G. Ulrich, R. Ziessel, A.
Harriman, Angew. Chem. Int. Ed. 2008, 47, 1184–1201; g) A.
Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891–4932; h) J. J.
Gassensmith, E. Arunkumar, L. Barr, J. M. Baumes, K. M. Di-
Vittorio, J. R. Johnson, B. C. Noll, B. D. Smith, J. Am. Chem.
Soc. 2007, 129, 15054–15059; i) Z. Lu, N. Liu, S. J. Lord, S. D.
Bunge, W. E. Moerner, R. J. Twieg, Chem. Mater. 2009, 21,
797–810; j) K. Kolmakov, V. N. Belov, J. Bierwagen, C. Ringe-
mann, V. Müller, C. Eggeling, S. W. Hell, Chem. Eur. J. 2010,
16, 158–166.
a) Y. Miyake, Y. Kikugawa, J. Heterocycl. Chem. 1983, 20, 349–
352; b) G. Field, P. R. Hammond (Dept. of Energy, USA), US
Pat. 5283336 (01. Feb. 1994); c) C. Berrier, J. C. Jacquesy, M. P.
Jouannetaud, A. Renoux, New J. Chem. 1987, 11, 605–609.
B. C. Ranu, S. Bhar, Org. Prep. Proc. Int. 1996, 28, 371–409.
M. E. Kuehne, J. B. Pitner, J. Org. Chem. 1989, 54, 4553–4569.
a) J.-L. Luche, J.-C. Damiano, J. Am. Chem. Soc. 1980, 102,
7926–7927; b) S. Sabetay, Bull. Soc. Chim. Fr. 1930, 47, 614–
620.
Y. Yamada, A. Akiba, S. Arima, C. Okada, K. Yoshida, F.
Itou, T. Kai, T. Satou, K. Takeda, Y. Harigaya, Chem. Pharm.
Bull. 2005, 53, 1277–1290.
a) M. A. Davis, S. O. Winthrop, R. A. Thomas, F. Herr, M.-P.
Charest, R. Gaudry, J. Med. Chem. 1964, 7, 88–94; b) L. F.
Fieser, E. B. Hershberg, J. Am. Chem. Soc. 1937, 59, 2331–
2335.
[14]
[15]
[16]
[17]
[18]
[19]
a) A. I. Meyers, D. L. Temple, J. Am. Chem. Soc. 1970, 92,
6646–6647; b) T. D. Nelson, A. I. Meyers, J. Org. Chem. 1994,
59, 2577–2580; c) J. Sedelmeier, T. Hammerer, C. Bolm, Org.
Lett. 2008, 10, 917–920.
[5]
a) The presence of the very strong electron-acceptor groups –
e.g., CF3 and CN – in position 9 of the xanthene core shifts
the absorption and emission maxima of the rhodamine dyes
far more to the red, but all these dyes are hydrolytically un-
stable, due to the addition of water and other nucleophiles to
C-9: J. Arden-Jacob, Neue langwellige Xanthen-Farbstoffe für
Fluoreszenzsonden und Farbstofflaser (Dissertation), Verlag
[10]
[20]
[21]
See ref., pp. 582–588.
a) K. H. Knauer, R. Gleiter, Angew. Chem. 1977, 89, 116–117;
Angew. Chem. Int. Ed. Engl. 1977, 16, 113–113; b) H. Willwohl,
J. Wolfrum, R. Gleiter, Laser Chem. 1989, 10, 63–72.
A. I. Meyers, D. L. Temple, R. L. Nolen, E. D. Mihelich, J.
Org. Chem. 1974, 39, 2778–2783.
[22]
Eur. J. Org. Chem. 2010, 3593–3610
© 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
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