Fluorescent nucleosides with an elongated rigid linker: attaching perylene to a nucleobase via a one-pot desilylation/Sonogashira reaction

Chistov, Alexey A.; Ivanov, Nikita M.; Kutyakov, S. V.; Устинов, Алексей Владимирович; Glybin, Anton V.; Streshnev, Philipp P.; Михура, И. В.; Korshun, Vladimir A.

doi:10.1016/j.tetlet.2016.09.050

Cited by 10 publications

(9 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These compounds showed a narrow band spectrum with the full-width half maxima in the range of ∼50 to 60 nm. The pattern of the emission spectra also indicated the presence of perylene units as observed in many reported perylene-based compounds. − …”

Section: Resultssupporting

confidence: 58%

Exploring Acceptor-Functionalized Perylenes as Hole Transport Materials for Solution Process Organic Light-Emitting Diodes

Kumar,

Sharma,

Thakur

et al. 2024

ACS Appl. Electron. Mater.

View full text Add to dashboard Cite

The high charge carrier mobility and organized solid-state structure of perylene-based materials enable them to be used in optoelectronics. The impressive luminance of organic lightemitting diodes (OLEDs) helps in improving visibility for both indoor and outdoor activities. Considering the good charge mobility of the perylene-based structures, we report perylenebased three molecular systems viz. PhPrPy, AnPrPy, and TPAPrPy, integrated with functionalized pyridines, leading to the formation of donor−acceptor (D−A) systems which were finally explored as hole transport materials (HTMs) for solution-process OLEDs. The pyridine units were functionalized with phenyl, pmethoxyphenyl, and triphenylamine functionalities. For theoretical screening, density functional theory was adopted for evaluating the molecules for their optimized geometries, highest occupied molecular orbital/lowest unoccupied molecular orbital energy levels, reorganization energies, and hole and electron distribution in the excited states. The theoretical reorganization energies and ionization potentials indicated their possible capability for hole transportation. The theoretical studies revealed that the incorporation of a triphenylamine unit in the molecular framework significantly reduced the hole reorganization energy. Based on theoretical predictions, we chose TPAPrPy as the most promising one for solution-process device fabrication. The fabricated green phosphorescent OLED with TPAPrPy as HTM showed good performance with power efficacy (PE), current efficacy (CE), and external quantum efficiency (EQE) of ∼77 lm/W, ∼78 cd/A and ∼22%, respectively. Given the PE, CE, and EQE of the present device, the important outcome of using TPAPrPy as HTM was a good balance between PE, CE, and EQE with a low trade-off.Importantly, low roll-off in PE, CE, and EQE was observed when measured at a brightness of 100 and 1000 cd/m 2 .

show abstract

Section: Resultssupporting

confidence: 58%

Exploring Acceptor-Functionalized Perylenes as Hole Transport Materials for Solution Process Organic Light-Emitting Diodes

Kumar,

Sharma,

Thakur

et al. 2024

ACS Appl. Electron. Mater.

View full text Add to dashboard Cite

show abstract

“…Perylenylethynyl nucleoside derivatives have low solubility in most solvents, which makes it difficult to purify them using column chromatography. Therefore, acylic protection of hydroxyl groups of the carbohydrate fragment is usually applied, which allows to increase the solubility of the sp-sp 2 coupling product and to carry out its chromatographic purification after this step [8,11,15,16]. The isobutyryl group was chosen as such a protective group.…”

Section: Resultsmentioning

confidence: 99%

5-(Perylen-3-ylethynyl)uracil Derivatives Inhibit Reproduction of Respiratory Viruses

et al. 2020

View full text Add to dashboard Cite

In this work, we describe the synthesis of 5-(perylen-3-ylethynyl)uridine and its ability to effectively inhibit the replication of respiratory disease pathogens in cell culture, namely: influenza A virus (IVA); type 3 parainfluenza virus (PIV-3); and human respiratory syncytial virus (RSV). Related known compounds were also analyzed: 5-(perylen-3-ylethynyl)-2′-deoxy-uridine; 5-(perylen-3-ylethynyl)-arabino-uridine; and 1-carboxymethyl-3-pivaloyloxymethyl-5-(perylen-3-ylethynyl)uracil.

show abstract

“…A synthetic strategy for the formation of perylene nucleoside containing elongated rigid link between hydrocarbon and nucleobase through Sonogashira cross coupling was developed by Chistov and coworkers in 2016 [127]. 5-iodo-2′-deoxyuridine 260 was protected by Propinaylation and then coupled with Trimethysilyl.…”

Section: In 2016mentioning

confidence: 99%

Palladium and Copper Catalyzed Sonogashira cross Coupling an Excellent Methodology for C-C Bond Formation over 17 Years: A Review

et al. 2020

View full text Add to dashboard Cite

Sonogashira coupling involves coupling of vinyl/aryl halides with terminal acetylenes catalyzed by transition metals, especially palladium and copper. This is a well known reaction in organic synthesis and plays a role in sp2-sp C-C bond formations. This cross coupling was used in synthesis of natural products, biologically active molecules, heterocycles, dendrimers, conjugated polymers and organic complexes. This review paper focuses on developments in the palladium and copper catalyzed Sonogashira cross coupling achieved in recent years concerning substrates, different catalyst systems and reaction conditions.

show abstract

Fluorescent nucleosides with an elongated rigid linker: attaching perylene to a nucleobase via a one-pot desilylation/Sonogashira reaction

Cited by 10 publications

References 47 publications

Exploring Acceptor-Functionalized Perylenes as Hole Transport Materials for Solution Process Organic Light-Emitting Diodes

Exploring Acceptor-Functionalized Perylenes as Hole Transport Materials for Solution Process Organic Light-Emitting Diodes

5-(Perylen-3-ylethynyl)uracil Derivatives Inhibit Reproduction of Respiratory Viruses

Palladium and Copper Catalyzed Sonogashira cross Coupling an Excellent Methodology for C-C Bond Formation over 17 Years: A Review

Contact Info

Product

Resources

About