Synthesis and optical properties of perylene diimide derivatives with triphenylene-based dendrons linked at the bay positions through a conjugated ethynyl linkage

Bagui, Mahuya; Dutta, Tanmoy; Zhong, Haizhen A.; Li, Shaohua; Chakraborty, Shibaji; Keightley, Andrew; Peng, Zhonghua

doi:10.1016/j.tet.2012.02.008

Cited by 30 publications

(18 citation statements)

References 63 publications

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“…The red‐shift in both UV/Vis and emission maxima of 3 and 4 was above 100 nm, (which was higher than the amount of red‐shift in compound 1 and 2 compared to bare PTE) suggest a more planar structures of 3 and 4 , as compared to compounds 1 and 2 (Figure S23–S24). Also, the absorbance spectra of all the target compounds were broader and lost their fine structures compared to the starting compounds due to the expansion of the conjugation . Similar Franck–Condon ratios in solution (≈ 1.0) showed that all compounds aggregate to the same degree at a low concentration of 12.5 µ m .…”

Section: Resultsmentioning

confidence: 94%

Modular Synthesis and Structure–Property Correlation of Pyrene – Rylene Dyes for Cellular Imaging

2020

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Polycyclic aromatic hydrocarbon with extended conjugation and broad absorption properties are interesting due to their easy accessibility, response to external stimuli and high stability. Herein, we report synthesis and full characterization of four compounds having multiple photoactive units in conjugation with a central pyrene group. The compound 2 with extended conjugation showed high fluorescence intensity in the solid state. Since the target molecules are non‐toxic and highly fluorescent, water dispersible nanoparticles were prepared from these molecules and explored for cellular imaging.

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Section: Resultsmentioning

confidence: 94%

Modular Synthesis and Structure–Property Correlation of Pyrene – Rylene Dyes for Cellular Imaging

2020

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“…Strong fluorescence enhancement at 596 nm was achieved upon the addition of BSA. This long fluorescence emission might be attributed the large π‐conjugation and donor and acceptor structure in 1 . Meanwhile, apparent red fluorescence emission can be observed under ultraviolet light by the naked eye (Fig.…”

Section: Resultsmentioning

confidence: 96%

A ‘turn‐on’ fluorescent chemosensor for quantification of serum albumin in aqueous solution at neutral pH

2015

Luminescence

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A fluorescent chemosensor 1 (4-diethylamino-2'-hydroxychalcone) for detecting serum albumin with long-wavelength emission, good selectivity and facile synthesis was reported. Upon the addition of bovine serum albumin (BSA) to an aqueous solution of 1 at neutral pH, a 'turn-on' fluorescence response was observed at 596 nm based on a hydrophobic binding mode between 1 and BSA. A linear range of 0.10-1.00 mg/mL and a detection limit of 9.1 µg/mL for BSA were obtained, respectively. Moreover, 1 was successfully applied to detect BSA in real bovine serum samples with satisfied recovery and accuracy, which suggested that 1 could serve as a valid and effective fluorescent chemosensor for quantification of BSA.

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“…Among the hydrophilic groups tested have been ionic groups, such as cationic ammonium as well as anionic carboxylate, sulfonate, and phosphonate groups, or non‐ionic residues such as polyglycerol, polyethylene glycol, and entire dendrons . Recently, supramolecular host‐guest complexation has been successfully used as an alternative, noncovalent method to inhibit aggregation of PDIs in water by using water‐soluble macrocycles, such as cucurbit[ n ]urils (CB n ) or cyclodextrins (CDs) .…”

Section: Introductionmentioning

confidence: 99%

Host‐Guest Complexation Affects Perylene‐Based Dye Aggregation

et al. 2020

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A fluorescent perylene-based dye (PDI) was designed with two aromatic moieties at the imide position of the perylene core. The dye displayed contrasting behavior with water-soluble macrocycles. Cucurbit[n]urils (CB7 and CB8) reduced the selfaggregation of the dye molecules, while sulfonatocalixarenes (SCX4 and SCX5) and sulfonato-β-cyclodextrin (S-β-CD) resulted in a complexation-enhanced aggregation. In regard to potential applications, the CB8 * PDI complex served as an excellent reporter pair inside cells to detect the uptake of neurotransmitters by fluorescence.

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Synthesis and optical properties of perylene diimide derivatives with triphenylene-based dendrons linked at the bay positions through a conjugated ethynyl linkage

Cited by 30 publications

References 63 publications

Modular Synthesis and Structure–Property Correlation of Pyrene – Rylene Dyes for Cellular Imaging

Modular Synthesis and Structure–Property Correlation of Pyrene – Rylene Dyes for Cellular Imaging

A ‘turn‐on’ fluorescent chemosensor for quantification of serum albumin in aqueous solution at neutral pH

Host‐Guest Complexation Affects Perylene‐Based Dye Aggregation

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