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Closing the Ring to Bring Up the Light: Synthesis of a Hexacyclic Acridinium Cyanine Dye
Author(s) -
Mahmood Tariq,
Wu Yilei,
Loriot Domitille,
Kuimova Marina,
Ladame Sylvain
Publication year - 2012
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.201200802
Subject(s) - cyanine , monomer , chemistry , fluorescence , photochemistry , quantum yield , photobiology , organic chemistry , polymer , optics , physics
The synthesis of a geometrically constrained and near‐planar hexacyclic acridinium cyanine dye 9 is reported. When compared to its unlocked and non‐fluorescent monomethine cyanine dye analogue 3 , this photostable dye emits in the green area of the spectrum with a remarkable quantum yield close to unity in organic solvents and above 0.5 in water. A detailed steady‐state and time‐resolved spectroscopic study revealed that dye 9 forms emissive aggregates in water, which are responsible for a red‐shifted and broadened emission band and longer emission lifetime, τ ≈33 compared to 6.5–7.0 ns for the monomeric dye. Dye 9 also binds strongly to DNA (both duplex and quadruplex) in its monomeric form and is very efficiently taken up by cells, in which it accumulates primarily into the nucleus.