Bioconjugate Chemistry
Communication
(
11) Weil, T., Reuther, E., and Mu
̈
llen, K. (2002) Shape-persistent,
CONCLUSION
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fluorescent polyphenylene dyads and a triad for efficient vectorial
In summary, we have synthesized and characterized a new
water-soluble membrane marker based on an amphiphilic
dendritic polyglycerol perylene imido dialkylester which forms
fluorescence quenched aggregates in water but becomes highly
green fluorescent when incorporated into a lipophilic environ-
ment, such as biological membranes. We could show that it can
be easily used as fluid phase marker for disordered domains in
artificial membranes and that it is efficiently taken up into living
cells following endocytic pathways. Due to its high quantum
yield, high photophysical stability, and easy modifiability on the
dendron side, it is an ideal platform to anchor and track
polyglycerol bound bioactive compounds in artificial or cellular
membranes.
transduction of excitation energy. Angew. Chem. 114, 1980−1984.
(12) Baffreau, J., Ordronneau, L., Leroy-Lhez, S., and Hudhomme, P.
(
2008) Fullerene C60 − perylene-3,4:9,10-bis(dicarboximide) light-
harvesting dyads: spacer length and bay-substituent effects on
intramolecular singlet and triplet energy transfer. J. Org. Chem. 73,
6142−6147.
(13) Kirmaier, C., Song, H.-e., Yang, E., Schwartz, J. K., Hindin, E.,
Diers, J. R., Loewe, R. S., Tomizaki, K.-y., Chevalier, F., and Ramos, L.
(
2010) Excited-state photodynamics of perylene-porphyrin dyads. 5.
Tuning light-harvesting characteristics via perylene substituents,
connection motif, and three-dimensional architecture. J. Phys. Chem.
B 114, 14249−14264.
(
̈
14) Flamigni, L., Ventura, B., You, C.-C., Hippius, C., and Wurthner,
F. (2007) Photophysical characterization of a light-harvesting tetra
naphthalene imide/perylene bisimide array. J. Phys. Chem. C 111, 622−
630.
ASSOCIATED CONTENT
Supporting Information
Experimental details about the synthesis and the experimental
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S
(15) Wu
blocks for functional supramolecular architectures. Chem. Commun. 14,
564−1579.
16) Wurthner, F. (2006) Bay-substituted perylene bisimides:
̈
rthner, F. (2004) Perylene bisimide dyes as versatile building
1
(
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Twisted fluorophores for supramolecular chemistry. Pure Appl.
Chem. 78, 2341−2349.
AUTHOR INFORMATION
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(17) Krieg, E., and Rybtchinski, B. (2011) Noncovalent water-based
materials: robust yet adaptive. Chem.Eur. J. 17, 9016−9026.
(18) Chen, Z., Lohr, A., Saha-Moller, C. R., and Wurthner, F. (2009)
̈
̈
Self-assembled π-stacks of functional dyes in solution: structural and
thermodynamic features. Chem. Soc. Rev. 38, 564−584.
Notes
(19) Gao, B., Li, H., Liu, H., Zhang, L., Bai, Q., and Ba, X. (2011)
The authors declare no competing financial interest.
Water-soluble and fluorescent dendritic perylene bisimides for live-cell
imaging. Chem. Commun. 47, 3894−3896.
ACKNOWLEDGMENTS
The authors thank the Deutsche Forschungsgemeinschaft
DFG) for financial support via the SFB 765 and acknowledge
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(
20) Wang, L., Xu, L., Neoh, K. G., and Kang, E.-T. (2011) Water-
soluble highly fluorescent poly[poly(ethylene glycol) methyl ether
methacrylate] for cell labeling. J. Mater. Chem. 21, 6502−6505.
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21) Weil, T., Abdalla, M. A., Jatzke, C., Hengstler, J., and Mullen, K.
(2005) Water-soluble rylene dyes as high-performance colorants for
the staining of cells. Biomacromolecules 6, 68−79.
(22) Peneva, K., Mihov, G., Nolde, F., Rocha, S., Hotta, J.-i.,
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dx.doi.org/10.1021/bc3005655 | Bioconjugate Chem. XXXX, XXX, XXX−XXX