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ChemComm
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COMMUNICATION
Journal Name
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Chem. Eur. J., 2016, 22, 6314; (b) J. JeDffOeIt:,1A0..10K3Vo9ieb/wCoA7, rCTtiCc.l0eS8Ou7n,6liAn1Fe.
Grunwald, O. Green, A. N. Nilsson, E. Eisenberg, T.
Ambjörnsson, F. Westerlund, E. Weinhold, D. Shabat, P. K.
Purohit and Y. Ebenstein, ACS Nano, 2016, 10, 9823.
Recent examples: (a) T. Sarkar, K. Selvakumar, L. Motiei and
D.
Margulies,
Nat.
Commun.,
2016,
7:11374,
doi:10.1038/ncomms11374; (b) L. Unger-Angel, B. Rout, T.
Ilani, M. Eisenstein, L. Motiei and D. Margulies, Chem. Sci.,
2015, 6, 5419.
Figure 4. Fluorescence microscopy image (left) of living Fibroblast cells incubated
5
6
(a) H. Kobayashi, M. Ogawa, R. Alford, P. L. Choyke and Y.
Urano, Chem. Rev., 2010, 110, 2620; (b) S. Nizamov, M. V.
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54, 2995.
with
1
(1 µM in PBS). Cell viability XTT assay (right) of primary human fibroblast,
HUVEC and macrophages incubated with
1
at different concentration.
In addition, the XTT assay test proved that 1 has no cytotoxic
effects even at high concentration, thus indicating 1 as an ideal
reagent for live cell imaging of different types of primary cells.
In conclusion, the design of the first water soluble
spirobifluorene-based molecule
1 allowed combining a large
Stokes shift and high QY in aqueous solution as well in organic
solvents. The presence of BSA induced a blue shifted emission
with increased QY, resulting in a nanomolar detection limit for
BSA in a no covalent labelled analysis. By using known site-
marker molecules, we observed the simultaneous presence of
hydrophobic and electrostatic interactions in the
1:BSA
complex. Interestingly, the variation of pH suggests an
enhancement of one interaction over the other, resulting in a
strong binding and intense emission in the whole pH range.
7
8
9
J. R. Lakowicz, Principles of Fluorescence Spectroscopy, 3rd ed.,
Kluwer Academic/Plenum Publishers, New York, 2006.
Y. Liu, J. Zhou, L. Wang, X. Hu, X. Liu, M. Liu, Z. Cao, D.
Shangguan and W. Tan, J. Am. Chem. Soc., 2016, 138, 12368.
(a) J. Mei, N. L. C. Leung, R. T. K. Kwok, J. W. Y. Lam and B. Z.
Tang, Chem. Rev., 2015, 115, 11718; (b) H. Qian, M. E. Cousins,
E. H. Horak, A. Wakefield, M. D. Liptak and I. Aprahamian, Nat.
Besides, at neutral pH the local polarity of
analogous to micelles formed by Triton X-100. The interaction
between aromatic rings in the supramolecular species BSA–
1:BSA system is
1
reduces the deactivation pathways and changes the polarity in
the local surroundings of the dye, inducing blue-shifted PL.
Chem., 2017, 9, 83.
Finally,
1 demonstrates that spirobifluorene derivatives may
10 H. Frisch, D. Spitzer, M. Haase, T. Basche, J. Voskuhl and P.
Besenius, Org. Biomol. Chem., 2016, 14, 5574.
provide useful tools for the imaging of biological pathways in
living cells due to their excellent solubility in aqueous solution
combined with high brightness and very low cytotoxicity.
11 T. P. I. Saragi, T. Spehr, A. Siebert, T. Fuhrmann-Lieker and J.
Salbeck, Chem. Rev., 2007, 107, 1011.
Spirobifluorene-based molecules emitting at lower energy and 12 (a) F. Polo, F. Rizzo, M. Veiga-Gutierrez, L. De Cola and S. Quici,
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Nomura, M. Yahiro, K. Endo, and C. Adachi, J. Phys. Chem. C
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able to address specific organelle are actually under
investigation in our laboratories.
F.R. thanks Prof. B. J. Ravoo for access to his laboratories and
fruitful discussion, Prof. Dr. G. Wilde and Priv.-Doz. Dr. C. A.
Strassert for the kind use of their instruments, Prof. G. 13 D. R. G. Ditter, A. S. Brown, J. D. Baker and J. N. Wilson, Org.
Biomol. Chem., 2015, 13, 9477.
14 CCDC 1565161 contains the supplementary
Fernandez for fruitful discussion and Deutscher Akademischer
Austauschdienst (DAAD) for fellowship. Judith Schmidt and Jana
Salich are acknowledged for the excellent technical support.
(4)
crystallographic data for this paper. These data can be
obtained free of charge from The Cambridge Crystallographic
15 H. Tong, Y. Hong, Y. Dong, M. Häussler, Z. Li, J. W. Y. Lam, Y.
Dong, H. H.-Y. Sung, I. D. Williams and B. Z. Tong, J. Phys.
Chem. B, 2007, 111, 11817.
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,
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