Fluorinated perylene diimides: synthesis, electrochemical–photophysical properties, and cellular imaging

Jia, Wang; Zhong, Shilong; Duan, Wenfeng; Gao, Baoxiang

doi:10.1016/j.tetlet.2014.12.112

Cited by 8 publications

(3 citation statements)

References 40 publications

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“…One oxidation peak at E pa =−0.508 (vs. Ag/AgCl) and two reduction peaks, E pc =−0.581 and −0.364 (vs. Ag/AgCl), were observed. This cyclic voltammogram is similar to those of PBIs in the literature that have one oxidation and two reduction peaks …”

Section: Resultssupporting

confidence: 83%

Aggregation Behavior and Electron‐Transfer Reaction of Dendritic Perylene Bisimide, Accompanied by the Formation of Highly Stable Anionic Radical Species

et al. 2017

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Ap olyethylene-glycol-functionalized perylene bisimide (PEPBI) was synthesized. Its concentration-, solventand temperature-dependent visible spectra were measured and its aggregation states were analyzed. PEPBI exists as an aggregate dimer in aqueous solution or predominantly as a monomer in organic solvents. The anionic surfactant sodium dodecylbenzenesulfonate (SDBS) can disperse PEPBI as a monomer in aqueous solution.T he fluorescenceo ft hese solutions dependso nt he concentration of PEPBI and SDBS.The reduction of aggregated PEPBI with Na 2 Si ss low and the monoanion radical as well as dianion speciesa re the main forms of monomer.P EPBI exists predominantly as monomers in DMF andr eacts with Na 2 Sm uch faster.I nterestingly, the anionic radical species exist in H-aggregate form at low PEPBI concentrationsa nd J-aggregation occurs at high concentration. The dianion species is EPR-silent and its color highly depends on its concentration in DMF.

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Section: Resultssupporting

confidence: 83%

Aggregation Behavior and Electron‐Transfer Reaction of Dendritic Perylene Bisimide, Accompanied by the Formation of Highly Stable Anionic Radical Species

et al. 2017

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“…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.

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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 .

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“…Absorption spectra values taken in water are 557 nm for BPPDI, 550 nm for BFPDI-1 and 548 nm for BFPDI-2. It shows red-schifted [28]. Figure 6.…”

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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Fluorinated perylene diimides: synthesis, electrochemical–photophysical properties, and cellular imaging

Cited by 8 publications

References 40 publications

Aggregation Behavior and Electron‐Transfer Reaction of Dendritic Perylene Bisimide, Accompanied by the Formation of Highly Stable Anionic Radical Species

Aggregation Behavior and Electron‐Transfer Reaction of Dendritic Perylene Bisimide, Accompanied by the Formation of Highly Stable Anionic Radical Species

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

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

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