Design and synthesis of novel fluorescence sensing perylene diimides based on photoinduced electron transfer

Georgiev, Nikolai I.; Sakr, Alaa R.; Bojinov, Vladimir B.

doi:10.1016/j.dyepig.2011.04.015

Cited by 112 publications

(56 citation statements)

References 50 publications

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“…6), the highest intensity is observed at the longest wavelength band [14]. This spectrum differs significantly from that of PDI(2)/PVA 269 -b-PAN 231 based micelles in aqueous solution (Fig.…”

Section: Photophysical Investigation Of Pdi (2) In Organic Solvent Ancontrasting

confidence: 50%

“…The dyes were prepared by analogy with the previously described procedures [14,35] refluxing perylene-3,4,9,10-tetracarboxylic anhydride 1 and corresponding amine in water/n-propanol media. The pure dyes 2-4 were obtained after removing the unreacted anhydride 1 and intermediate monoimide-monoanhydride with boiling 5% aqueous sodium hydroxide.…”

Section: Design Synthesis and Characterization Of Novel Pdi/pva-b-pamentioning

confidence: 99%

“…They are easy of synthetic modification [2] and widely used n-type materials for organic electronic devices such as solar cells [3][4][5], field-effect transistors [6][7][8], light-emitting diodes [9][10][11]. They have been also used in liquid crystals [12,13], as chemosensing materials [14][15][16] and dyes in photodynamic therapy [17]. Due to their unique properties PDI chromophores could be successfully applied in biological environment as high-performance fluorescent labels.…”

Section: Introductionmentioning

confidence: 98%

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Novel nanosized water soluble fluorescent micelles with embedded perylene diimide fluorophores for potential biomedical applications: Cell permeability, localization and cytotoxicity

Bryaskova

Georgiev

Dimov

et al. 2015

Materials Science and Engineering: C

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Section: Photophysical Investigation Of Pdi (2) In Organic Solvent Ancontrasting

confidence: 50%

Section: Design Synthesis and Characterization Of Novel Pdi/pva-b-pamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

See 1 more Smart Citation

Novel nanosized water soluble fluorescent micelles with embedded perylene diimide fluorophores for potential biomedical applications: Cell permeability, localization and cytotoxicity

Bryaskova

Georgiev

Dimov

et al. 2015

Materials Science and Engineering: C

Self Cite

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“…While PDI was initially used exclusively as industrial pigments as red vat dyes, nowadays applications of PDI are in the field of photo-electronic material, dye lasers, organic light-emitting diodes (OLED) [4,5], chemosensing materials [6], biosensing [7]. It has electron transporting character.…”

Section: Introductionmentioning

confidence: 99%

A Review on Perylene-3,4,9,10-Tetracarboxylic Acid Diimide Molecules

Birel¹

2017

Celal Bayar Üniversitesi Fen Bilimleri Dergisi

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The aim of this article is to inform about perylene-3,4,9,10-tetracarboxylic acid dimide (PDI) derivatives. Also, it is to give short and simple information about optical properties and using fields. Perylene-3,4,9,10-tetracarboxylic acid dimide derivatives known as perylene diimides are material of highly conjugated molecule. PDIs exhibit strong absorptions within the range of 400-450 nm (B band) and 500-700 nm (Q band). Perylene diimide dyes show generally characteristic absorption peaks at 458, 490, 526 nm. These absorption peaks are matched by the corresponding emission peaks at 540, 576, 624 nm, respectively. It has donor core and acceptor carbonyl groups. Perylene dimide has good electron mobility, high fluorescence quantum yields, strong absorption in the visible region, photostability, thermal stability, good semi-conductivity. These properties benefit them application of electronic material. Applications of PDIs are in the field of photo-electronic material, dye lasers, organic light-emitting diodes, and chemosensing materials.

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“…Dyes-cored fluorescent dendrimers have been propsed to solve these problems [6]. Instead of synthesizing dye-cored dendrimer via divergent approach, directly attaching dendrimers to fluorescent dye may simplify the preparation process [30]. Fan-shaped PAMAM dendron, as a kind of special PAMAM dendrimer, could be modified at the periphery and the focal point of dendron [24,31].…”

Section: Introductionmentioning

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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Design and synthesis of novel fluorescence sensing perylene diimides based on photoinduced electron transfer

Cited by 112 publications

References 50 publications

Novel nanosized water soluble fluorescent micelles with embedded perylene diimide fluorophores for potential biomedical applications: Cell permeability, localization and cytotoxicity

Novel nanosized water soluble fluorescent micelles with embedded perylene diimide fluorophores for potential biomedical applications: Cell permeability, localization and cytotoxicity

A Review on Perylene-3,4,9,10-Tetracarboxylic Acid Diimide Molecules

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

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