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Water‐Soluble Triarylborane Chromophores for One‐ and Two‐Photon Excited Fluorescence Imaging of Mitochondria in Cells
Author(s) -
Griesbeck Stefanie,
Zhang Zuolun,
Gutmann Marcus,
Lühmann Tessa,
Edkins Robert M.,
Clermont Guillaume,
Lazar Adi.,
Haehnel Martin,
Edkins Katharina,
Eichhorn Antonius,
BlanchardDesce Mireille,
Meinel Lorenz,
Marder Todd B.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602639
Subject(s) - chromophore , fluorescence , photochemistry , quantum yield , two photon excitation microscopy , fluorescence lifetime imaging microscopy , excited state , fluorescence microscope , two photon absorption , photobleaching , acceptor , thiophene , chemistry , materials science , biophysics , laser , optics , biology , physics , organic chemistry , atomic physics , condensed matter physics
Three water‐soluble tetracationic quadrupolar chromophores comprising two three‐coordinate boron π‐acceptor groups bridged by thiophene‐containing moieties were synthesised for biological imaging applications. Compound 3 containing the bulkier 5‐(3,5‐Me 2 C 6 H 2 )‐2,2′‐(C 4 H 2 S) 2 ‐5′‐(3,5‐Me 2 C 6 H 2 ) bridge is stable over a long period of time, exhibits a high fluorescence quantum yield and strong one‐ and two‐photon absorption (TPA), and has a TPA cross section of 268 GM at 800 nm in water. Confocal laser scanning fluorescence microscopy studies in live cells indicated localisation of the chromophore at the mitochondria; moreover, cytotoxicity measurements proved biocompatibility. Thus, chromophore 3 has excellent potential for one‐ and two‐photon‐excited fluorescence imaging of mitochondrial function in cells.