Solid-phase methods for the synthesis of cyanine dyes.
We report here a series of studies that explore solid-phase methodologies for the synthesis of various cyanine dyes. The scope of the previously reported catch-and-release method using sulfonyl chloride resin(1) has now been extended to include pentamethine and water-soluble cyanine dyes. We also report a new and chemically distinct synthetic strategy, employing the stepwise attack of heterocyclic carbon nucleophiles on immobilized polyene-chain precursors, allowing the clean synthesis of hydrophobic and hydrophilic trimethine and pentamethine dyes from more easily obtained starting materials. Overall, both approaches appear to be robust and versatile strategies to delivering a wide range of cyanine-based dyes in high purity.
Mason
Stephen J
SJ
University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.
Hake
Jen L
JL
Nairne
James
J
Cummins
W Jon
WJ
Balasubramanian
Shankar
S
D002232:Carbocyanines / Q000138:chemical synthesis*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D004396:Coloring Agents / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure
D002232:Carbocyanines; D004396:Coloring Agents; D007202:Indicators and Reagents