Synthese von nichtsymmetrisch substituierten Perylen‐Fluoreszenzfarbstoffen

Kaiser, H.; Lindner, Jörg; Langhals, Heinz

doi:10.1002/cber.19911240319

Cited by 150 publications

(135 citation statements)

References 17 publications

(1 reference statement)

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“…The synthesis started with compound 3 and applying the well established strongly hydrolysing mixture of KOH in tert-butyl alcohol 14 resulted in a stepwise degradation of the carboxylic imide groups. The primary product of the hydrolysis proved to be insoluble and thus became excluded from further reaction.…”

Section: Resultsmentioning

confidence: 99%

A versatile standard for bathochromic fluorescence based on intramolecular FRET

Langhals

Walter

Rosenbaum

et al. 2011

Phys. Chem. Chem. Phys.

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A perylene and a terrylene tetracarboxylic bisimide dyad was prepared in which an efficient energy transfer from the former to the latter is observed. The absorption spectrum of this compound covers a broad range. Bathochromic fluorescence with a high quantum yield was obtained independent of excitation wavelengths (l o 655 nm). The dyad can be recommended for the use of calibrating fluorescence spectrometers, as well as a fluorescence standard in the bathochromic region.

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Section: Resultsmentioning

confidence: 99%

A versatile standard for bathochromic fluorescence based on intramolecular FRET

Langhals

Walter

Rosenbaum

et al. 2011

Phys. Chem. Chem. Phys.

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“…Sensitiser and acceptor perylene-acrylate monomers were synthesised using modified literature procedures, starting from commercially available 3,4,9,10-perylenetetracarboxylic dianhydride [36][37][38][39][40] (Figures 1 and 2). Creation of a polymer pendant group based on the PDI center requires an asymmetric PDI monomer.…”

Section: Synthesis Of Monomers and Polymersmentioning

confidence: 99%

Energy transfer in pendant perylene diimide copolymers

et al. 2016

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We report the synthesis, characterisation and polymerisation of two novel asymmetric perylene diimide acrylate monomers. The novel monomers form a sensitiser-acceptor pair capable of undergoing Förster resonance energy transfer, and were incorporated as copolymers with tert-butyl acrylate. The tert-butyl acrylate units act as spacers along the polymer chain allowing high concentrations of dye while mitigating aggregate quenching, leading to persistent fluorescence in the solid state at high concentrations of up to 0.3 M. Analysis of fluorescence kinetics showed efficient energy transfer between the optically dense sensitiser and the lower concentration acceptor luminophores within the polymer. This reduced reabsorption within the material demonstrates that the copolymer-scaffold energy transfer system has potential for use in luminescent solar concentrators.

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“…This strategy has several advantages compared to previously reported methods. Firstly, the mild amidation reaction can protect peripheral ester from hydrolyzing [43,44]. Secondly, directly conjugating the PAMAM dendrons to dyes avoids complicated purification procedures.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of water-soluble dye-cored poly(amidoamine) dendrimers for long-term live cell imaging

Cai

Zhang

et al. 2018

Sci. China Mater.

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Hydrophilic dendrimers, especially poly(amidoamine) (PAMAM) dendrimers are widely applied in modifying fluorescent dyes to endow them with water solubility and biocompatibility for biologic fluorescence imaging. Common preparation strategies of fluorescent dendrimers including encapsulating dyes or attaching dyes at periphery of dendrimers might cause uncertain constituent and lower biocompatibility. Here, we have developed a series of watersoluble fluorescent dendrimers with dye as core and fanshaped PAMAM as arms. Carboxylated perylene bisimides (PBI) dye and squarylium indocyanine (SICy) dye were conjugated with PAMAM dendrons by amidation to obtain a series of fluorescent dendrimers with enhanced water-solubility. Two PBI based dendrimers (PBI-G2.5 and PBI-G1.5) were chosen as model compounds for further optical, selfassembly and biological studies. In aqueous environment, PBI-G2.5 exhibited strong fluorescence, small size (~30 nm) and slightly positive surface charge (~2.46 mV), which are ideal for biomedical applications. In vitro assays demonstrated that PBI-G2.5 nanoparticles accumulated in the cytoplasm of HeLa cells with rapid cellular uptake. The strong fluorescence in HeLa cells remained for over 48 h. To conclude, our study provides an effective strategy for preparing water-soluble fluorescent dendrimers towards long-term live cell imaging.

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Synthese von nichtsymmetrisch substituierten Perylen‐Fluoreszenzfarbstoffen

Cited by 150 publications

References 17 publications

A versatile standard for bathochromic fluorescence based on intramolecular FRET

A versatile standard for bathochromic fluorescence based on intramolecular FRET

Energy transfer in pendant perylene diimide copolymers

Synthesis of water-soluble dye-cored poly(amidoamine) dendrimers for long-term live cell imaging

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