Closing the ring to bring up the light: synthesis of a hexacyclic acridinium cyanine dye.
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.
COMSATS, Institute of Information Technology, Abbottabad Campus, Pakistan.
Tariq
T
Mahmood
Yilei
Y
Wu
Domitille
D
Loriot
Marina
M
Kuimova
Sylvain
S
Ladame
D000166:Acridines / Q000737:chemistry*; D002232:Carbocyanines / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D008027:Light; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry*; D014867:Water
D000166:Acridines; D002232:Carbocyanines; D005456:Fluorescent Dyes; D012997:Solvents; D014867:Water; D004247:DNA; C019071:quinaldine blue