Spectroscopy and laser action of the “red perylimide dye” in various solvents

Gvishi, Raz; Reisfeld, R.; Burshtein, Z.

doi:10.1016/0009-2614(93)85142-b

Cited by 218 publications

(148 citation statements)

References 11 publications

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“…Indeed, the photoluminescence (PL) spectrum of 1 (see Fig. 2) exhibits a (somewhat structured) band at 619 nm, similar to the fluorescence spectra of previously reported PDI compounds, 17 and different to the conventional phosphorescence spectra of Ir-complexes. The high PL quantum yield (55%, by irradiation of the PDI unit) and the low lifetime (3.0 ns) recorded for the fluorescence of 1 are suitable to expect high-efficient electroluminescence (EL) devices.…”

supporting

confidence: 73%

Efficient deep-red light-emitting electrochemical cells based on a perylenediimide-iridium-complex dyad

et al. 2009

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A two-layer light-emitting electrochemical cell device based on a new perylenediimide-iridium-complex dyad is presented emitting in the deep-red region with high external quantum efficiencies (3.27%).Light-emitting electrochemical cells (LECs) based on ionic transition-metal complexes are among the simplest types of organic light-emitting devices (OLEDs). Their configuration mainly consists of an amorphous film of the active compound placed in between two electrodes.1 In spite of the disadvantages of LECs compared to OLEDs, like long turn-on time, shorter lifetimes, and lower efficiencies, LECs offer the advantage of using a less-reactive cathode material (aluminium instead of calcium or magnesium) and hence do not require stringent protection from environmental oxygen and water.Currently, the most widely used compounds in singlecomponent LEC devices are based on homoleptic complexes of Ru(II) and biscyclometalated heteroleptic complexes of Ir(III) whose positive charge is balanced by large negative counterions such as hexafluorophosphate.1 Their use in LECs is mainly due to their high phosphorescence emission quantum yields, short excited triplet state lifetimes and photochemical stability.2,3 However, complexes which give rise to efficient devices are not available for the deep-red region. This can be fulfilled by perylenediimides (PDIs), which present an exceptional photochemical stability, are strong light absorbers in the visible and show high fluorescence quantum yields, [4][5][6] which makes them interesting candidates for OLEDs. However, PDIs are poor hole conductors, which makes them unsuitable for single-component type devices. LECs additionally rely on the presence of mobile ions, and hence the emitting species must be compatible on the nanoscale with charged species. Single-layer LECs using PDI as n-type emissive material and lithium triflate have been recently reported showing red emission at high applied bias (+8 V). 7A polyimide LEC incorporating perylene and tri(ethylene oxide) moieties has been also studied showing a much more intensified electroluminescence than the respective polyimide LED. 8Taking into account the previous considerations, we decided to look for a synergistic collaboration between an ionic iridium(III) complex (that functions as the hole conductor and high phosphorescence emitter) and a PDI red fluorescent emitter (that functions as the electron conductor), in an attempt to achieve a high efficiency in the system. Moreover, the covalent linking of the moieties should increase the thermal stability, while avoiding phase separation processes. With this idea in mind, we have synthesized a new dyad consisting of a PDI derivative linked with an ionic iridium complex. The new dyad 1, see Scheme 1, is used as the single active component in a double-layer LEC device, showing efficient deep-red electroluminescence.The synthesis of the [PDI-iridium]PF 6 dyad 1 is outlined in Scheme 1. Condensation of tetra-tert-octylphenoxy monoanhydride monoimide 2 with 5-amino-1,10-phenanthroline 9 us...

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confidence: 73%

Efficient deep-red light-emitting electrochemical cells based on a perylenediimide-iridium-complex dyad

et al. 2009

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“…This is due to weakening of the hydrogen bonding between the imide and the wheel by competing interactions with the solvent. perylene red (F = 0.96) [27] 0.94 0.91 0.63 cresyl violet (F = 0.54) [28] 0 The spectral changes make the perylene diimide a suitable chromophore for reporting the position of the wheel on the axle. The presence of the wheel also gives rise to an increase of the reduction potentials indicating a stabilization of the anionic species by the wheel.…”

Section: Resultsmentioning

confidence: 99%

Fluorescent Perylene Diimide Rotaxanes: Spectroscopic Signatures of Wheel–Chromophore Interactions

Baggerman

Jagesar

Vallée

et al. 2007

Chemistry A European J

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[2]- and [3]-rotaxanes with a tetraphenoxy perylene diimide core were synthesized. Hydrogen bonding between the wheel and the imide changes the optical properties of the perylene chromophore: the absorption and fluorescence spectra are red-shifted. The decay times of the rotaxanes are shorter in comparison with that of the axle. Single molecule fluorescence measurements reveal relatively narrow distributions of emission maxima and decay times. The averages are in agreement with ensemble measurements. The observed red shifts make the perylene diimide a suitable chromophore for sensing the position of the wheel on the axle.

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“…In recent years there has been much industrial interest in developing pigment nanoparticles and particularly nanocrystals as colorants. [179] A second point of interest beyond the colorant aspect is the use of "functional dyes" as active components for xerography, [180] optical switches, [181] laser-dyes, [182] photovoltaic cells, [161] optical recording, [183] light-emitting diodes, [184] or as tracers in fluorescence analytical assays. [185] A third, more recent, research field arises from the idea of using light as a way to address single molecules.…”

Section: Rylene Dyes For Single-molecule Spectroscopymentioning

confidence: 99%

The Chemistry of Organic Nanomaterials

2005

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The development of nanotechnology using organic materials is one of the most intellectually and commercially exciting stories of our times. Advances in synthetic chemistry and in methods for the investigation and manipulation of individual molecules and small ensembles of molecules have produced major advances in the field of organic nanomaterials. The new insights into the optical and electronic properties of molecules obtained by means of single-molecule spectroscopy and scanning probe microscopy have spurred chemists to conceive and make novel molecular and supramolecular designs. Methods have also been sought to exploit the properties of these materials in optoelectronic devices, and prototypes and models for new nanoscale devices have been demonstrated. This Review aims to show how the interaction between synthetic chemistry and spectroscopy has driven the field of organic nanomaterials forward towards the ultimate goal of new technology.

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Spectroscopy and laser action of the “red perylimide dye” in various solvents

Cited by 218 publications

References 11 publications

Efficient deep-red light-emitting electrochemical cells based on a perylenediimide-iridium-complex dyad

Efficient deep-red light-emitting electrochemical cells based on a perylenediimide-iridium-complex dyad

Fluorescent Perylene Diimide Rotaxanes: Spectroscopic Signatures of Wheel–Chromophore Interactions

The Chemistry of Organic Nanomaterials

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