title: Bright, color-tunable fluorescent dyes based on π-expanded diketopyrrolopyrroles.
abstract: A synthetic approach to the structurally diverse family of π-expanded diketopyrrolopyrroles is described. A three-step strategy appears to be very general and starts with the preparation of diketopyrrolopyrroles followed by N-alkylation with bromoacetaldehyde diethyl acetal and electrophilic aromatic substitution. The final reaction regioselectively furnishes S-shaped, violet and blue functional dyes of previously unknown structure. New dyes possess sharp absorption and emission peaks, with very high molar absorption coefficients and reasonable fluorescence quantum yields. As a proof of principle, cell uptake of selected dye was demonstrated.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52 01-224 Warsaw, Poland.
authors.forename: Marek
authors.initials: M
authors.lastname: Grzybowski
authors.forename: Eliza
authors.initials: E
authors.lastname: Glodkowska-Mrowka
authors.forename: Tomasz
authors.initials: T
authors.lastname: Stoklosa
authors.forename: Daniel T
authors.initials: DT
authors.lastname: Gryko
mesh_terms: D003116:Color; D020650:Combinatorial Chemistry Techniques; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D008856:Microscopy, Fluorescence; D008958:Models, Molecular; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013050:Spectrometry, Fluorescence
chemical_list: D005456:Fluorescent Dyes; D011758:Pyrroles