Highly water-soluble neutral near-infrared emissive BODIPY polymeric dyes
- 15 December 2011
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of Materials Chemistry
- Vol. 22 (6), 2781-2790
- https://doi.org/10.1039/c2jm14920f
Abstract
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).Keywords
This publication has 26 references indexed in Scilit:
- Highly Water-Soluble Neutral BODIPY Dyes with Controllable Fluorescence Quantum YieldsOrganic Letters, 2010
- Deep‐red emissive conjugated poly(2,6‐BODIPY‐ethynylene)s bearing alkyl side chainsJournal of Polymer Science Part A: Polymer Chemistry, 2009
- Synthesis and Optical Properties of Red and Deep-Red Emissive Polymeric and Copolymeric BODIPY DyesChemistry of Materials, 2009
- Color Tuning of Polyfluorene Emission with BODIPY MonomersMacromolecules, 2009
- A Panchromatic Boradiazaindacene (BODIPY) Sensitizer for Dye-Sensitized Solar CellsOrganic Letters, 2008
- The Chemistry of Fluorescent Bodipy Dyes: Versatility UnsurpassedAngewandte Chemie-International Edition, 2008
- Self-Assembly of Fluorescent Amphipathic Borondipyrromethene Scaffoldings in Mesophases and OrganogelsChemistry of Materials, 2006
- Synthesis and functionalization of a highly fluorescent and completely water-soluble poly(para-phenyleneethynylene) copolymer for bioconjugationChemical Communications, 2006
- Design, synthesis, and biological evaluation of BODIPY®–erythromycin probes for bacterial ribosomesBioorganic & Medicinal Chemistry Letters, 2006
- Temperature dependence of collagen fluorescencePhotochemical & Photobiological Sciences, 2006