Towards highly fluorescent and water-soluble perylene dyes.
A systematic approach towards highly fluorescent, water-soluble perylene-3,4:9,10-tetracarboxylic acid diimide chromophores is presented. Water solubility was introduced first through the attachment of four hydrophilic substituents onto the bay region of the perylene dye. Positively and negatively charged groups were then applied to the chromophore, and their number and their distance from the aromatic scaffold were systematically varied. To suppress aggregation, the chromophore was further isolated within a dendritic shell. Such variation of structural features and a thorough investigation of the resulting optical properties facilitated the first synthesis of perylene-3,4:9,10-tetracarboxylic acid diimides combining the properties of water solubility and fluorescence quantum yields (FQYs) close to unity, which makes them attractive as high-performance fluorescence probes in aqueous media.
Kohl
Christopher
C
Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128 Mainz, Germany.
Weil
Tanja
T
Qu
Jianqiang
J
Müllen
Klaus
K
D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D007094:Imides / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D010569:Perylene / Q000031:analogs & derivatives*; D010777:Photochemistry; D012995:Solubility; D013050:Spectrometry, Fluorescence; D013053:Spectrophotometry; D014867:Water / Q000737:chemistry
D005456:Fluorescent Dyes; D007094:Imides; D014867:Water; D010569:Perylene