Synthesis and properties of fluorescent bis-quaternized perylene dyes

Deligeorgiev, Todor; Zaneva, D.; Петков, Иван; Timcheva, Il.; Sabnis, R. W.

doi:10.1016/0143-7208(94)87012-8

Cited by 23 publications

(13 citation statements)

References 4 publications

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“…[26] Compounds 4 a, [27] 4 b, [28,26] and 4 c [26] are known from previous studies, none of which examined their detailed pHsensing behaviour. Compounds 1 a and b, 2 and 4 a ± c were synthesized according to one-step procedures; 3 was prepared from 2 by acetylation.…”

Section: Resultsmentioning

confidence: 99%

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Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths

Daffy¹,

Silva²,

Gunaratne³

et al. 1998

Chem. Eur. J.

132

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N-(aminoalkyl)-4-chloronaphthalene-1,8-dicarboximides 1, N-(aminoalkyl)-4-acetamidonaphthalene-1,8-dicarboximides 3 and N,N'-bis(aminoalkyl)-perylene-3,4:9,10-tetracarboxydiimides 4 show good fluorescent off ± on switching in aqueous alcoholic solution with protons as required for fluorescent PET sensor design. The excitation wavelengths lie in the ultraviolet (l max 345 and 351 nm) for 1 and 3 and in the blue-green (l max 528, 492 and 461 nm) for 4; the emission wavelengths lie in the violet (l max 408 nm) for 1, in the blue (l max 474 nm) for 3 and in the yellow-orange (l max 543 and 583 nm) for 4. Compound 4 b shows substantial fluorescence enhancement with protons when immobilized in a poly(vinylchloride) matrix, provided that 2-nitrophenyloctyl ether plasticizer and potassium tetrakis(4-chlorophenyl)borate additive are present to prevent dye crystallization and to facilitate proton diffusion into the membrane, respectively.

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Section: Resultsmentioning

confidence: 99%

“…[26] In the event, the fluorescence of 4 a and c is conveniently excitable at the isosbestic points of 470 nm and that of 4 b at 452 nm. The longer wavelength of 528 nm can also be used with suitable correction for absorbance changes if so desired.…”

mentioning

confidence: 99%

Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths

Daffy¹,

Silva²,

Gunaratne³

et al. 1998

Chem. Eur. J.

132

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“…Synthesis : Perylene bis(2‐ethyltrimethylammonium X − imides) (Petma + X − ) are known compounds,16, 21 the various salts are readily interchangeable via ion exchange. Here we synthesize Petma + Cl − by a simpler method than previously reported, employing a single step in water and making the other ions from it.…”

Section: Methodsmentioning

confidence: 99%

A Self‐Doping, O₂‐Stable, n‐Type Interfacial Layer for Organic Electronics

Reilly

Hains

Chen

et al. 2012

Advanced Energy Materials

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Solid fi lms of a water-soluble dicationic perylene diimide salt, perylene bis(2ethyltrimethylammonium hydroxide imide), Petma + OH − , are strongly doped n-type by dehydration and reversibly de-doped by hydration. The hydrated fi lms consist almost entirely of the neutral perylene diimide, PDI, while the dehydrated fi lms contain ∼ 50% PDI anions. The conductivity increases by fi ve orders of magnitude upon dehydration, probably limited by fi lm roughness, while the work function decreases by 0.74 V, consistent with an n-type doping density increase of ∼ 12 orders of magnitude. Remarkably, the PDI anions are stable in dry air up to 120 ° C. The work function of the doped fi lm, ϕ (3.96 V vs. vacuum), is unusually negative for an O 2 -stable contact. Petma + OH − is also characterized as an interfacial layer, IFL, in two different types of organic photovoltaic cells. Results are comparable to state of the art cesium carbonate IFLs, but may improve if fi lm morphology can be better controlled. The fi lms are stable and reversible over many months in air and light. The mechanism of this unusual self-doping process may involve the change in relative potentials of the ions in the fi lm caused by their deshielding and compaction as water is removed, leading to charge transfer when dry. 456 www.MaterialsViews.com www.advenergymat.de

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“…Symmetric PTCDIs can be afforded in different conditions. The most diffused procedure employs a mixture of the chosen primary amine in quinoline at high temperature, [63] but Langhals et al have developed a strategy based on the employ of imidazole as base and solvent, and zinc acetate as catalyst. [64] Under basic alcoholic conditions, he and his co-workers have observed the rearrangement of PTCDIs to the lactame ring contracted by-product.…”

Section: Imide Functionalizationmentioning

confidence: 99%

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Synthesis and properties of fluorescent bis-quaternized perylene dyes

Cited by 23 publications

References 4 publications

Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths

Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths

A Self‐Doping, O₂‐Stable, n‐Type Interfacial Layer for Organic Electronics

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Synthesis and properties of fluorescent bis-quaternized perylene dyes

Cited by 23 publications

References 4 publications

Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths

Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths

A Self‐Doping, O2‐Stable, n‐Type Interfacial Layer for Organic Electronics

Technological Applications

Contact Info

Product

Resources

About

A Self‐Doping, O₂‐Stable, n‐Type Interfacial Layer for Organic Electronics