Journal
JOURNAL OF MATERIALS CHEMISTRY
Volume 22, Issue 6, Pages 2781-2790Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2jm14920f
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Funding
- NIH [1R43CA134039-01]
- 21st Century Jobs Fund of Michigan [06-1-P1-0283]
- National Science Foundation
- ALS Therapy Alliance
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1048655] Funding Source: National Science Foundation
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Three highly water-soluble near-infrared emissive polymeric BODIPY dyes (polymers A-C) were prepared by the palladium-catalyzed Suzuki polymerization of highly water-soluble 2,6-diiodo-3,5-distyryl-BODIPY dyes with 1,4-phenyldiboronic acid and 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-di[1-[2-(2-methoxyethoxy)ethoxy]ethyl]fluorene, respectively. Partial replacement of fluorine subunits of BODIPY cores at 4,4-positions of polymer C with ethynyl subunits resulted in a highly water-soluble BODIPY polymeric dye (polymer D). Polymers A-D show solubility of at least 20 mg mL(-1) in aqueous solution. For comparison purposes, polymers E and F were prepared by palladium-catalyzed Sonogashira polymerization of highly water-soluble 2,6-diiodo-3,5-distyryl-BODIPY dye with highly water-soluble 1,4-diethynylbenzene and 2,6-diethynyl BODIPY dye bearing branched oligo(ethylene glycol) methyl ether residues, respectively. Upon comparison, polymer E shows low solubility in aqueous solution (0.1 mg mL(-1)), whereas polymer F is almost insoluble in aqueous solution (less than 0.05 mg mL(-1)), but both are soluble in organic solvents such as chloroform, DMSO and DMF (at least 10 mg mL(-1)).
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