title: Solid-phase methods for the synthesis of cyanine dyes.
abstract: 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.
authors.affiliation: University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K.
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Mason
authors.forename: Jen L
authors.initials: JL
authors.lastname: Hake
authors.forename: James
authors.initials: J
authors.lastname: Nairne
authors.forename: W Jon
authors.initials: WJ
authors.lastname: Cummins
authors.forename: Shankar
authors.initials: S
authors.lastname: Balasubramanian
mesh_terms: 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
chemical_list: D002232:Carbocyanines; D004396:Coloring Agents; D007202:Indicators and Reagents