Terrylenimides: New NIR Fluorescent Dyes

Holtrup, F. O.; Müller, G.; Quante, Heribert; Feyter, Steven De; Schryver, F. C. De; Müllen, Kläus

doi:10.1002/chem.19970030209

Cited by 197 publications

(133 citation statements)

References 27 publications

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“…Initially, the use of asymmetric perylene monoimides (PMIs, 12) was a straightforward method ( Figure 2) for achieving this goal. [19] PMI, the most important building block, can be made via one-pot reaction including imidization and decarboxylation …”

Section: Reviewmentioning

confidence: 99%

Perylene Imides for Organic Photovoltaics: Yesterday, Today, and Tomorrow

Li¹,

Wonneberger²

2012

Advanced Materials

848

578

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Perylene imides have been an object of research for 100 years and their derivatives are key n-type semiconductors in the field of organic electronics. While perylene diimides have been applied in many electronic and photonic devices, their use can be traced back to the first efficient organic solar cell. By functionalizing different positions of the in total 12 positions (four peri, four bay, and four ortho-positions) on the perylene core, perylene imides with significantly different optical, electronic and morphological properties may be prepared. Perylene imides and their derivatives have been used in several types of organic photovoltaics, including flat-, and bulk-heterojunction devices as well as dye-sensitized solar cells. Additionally perylene imides-based copolymers or oligomers play an important role in single junction devices. In this review, the relationship between the photovoltaic performance and the structure of perylene imides is discussed.

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Section: Reviewmentioning

confidence: 99%

Perylene Imides for Organic Photovoltaics: Yesterday, Today, and Tomorrow

Li¹,

Wonneberger²

2012

Advanced Materials

848

578

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“…Recent studies have shown that doping Alq 3 with highly fluorescent molecules increases the PL quantum yield and the morphological stability of the composite materials, producing devices with enhanced EL quantum efficiencies, good luminous power efficiencies and prolonged lifetimes [166 -168]. Thus, derivatives of perylene (77) [109,169], naphthacene (78) [163], anthracene (79) [168,170], quinacridone (80) [109,171], pyrromethenedifluoroborate (81) [172] or squarilium (82) [173] (Fig. 14), among other highly fluorescent molecules [160], have been used as dopants with different electron-and hole-transporting materials.…”

Section: Low Molecular Weight Electroluminescent Materialsmentioning

confidence: 99%

The chemistry of electroluminescent organic materials

Segura¹

1998

Acta Polym.

287

200

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Electroluminescence has been a subject of interest for several decades because of its many applications in areas such as telecommunications or information displays. Light‐emitting diodes using p‐n junctions of inorganic semiconductors have dominated the field in the last twenty years; however, efficient blue emission has only recently been achieved and inorganic semiconductors are difficult to form over large areas, making the process uneconomic. During the last decade, an explosive growth of activity in the area of organic electroluminescence has occurred in both academia and industry, stimulated by the promise of light‐emitting plastics for the fabrication of large, flexible, inexpensive and efficient screens to be used in different applications. Thus, a substantial amount of research is presently directed towards color control and improvement of manufacturability and reliability of devices in order to make their commercialization viable. A great deal of work has been carried out by physicists and materials scientists concerned with the preparation of different device structures and with the use of different techniques for device manufacture. However, all this work would not be possible without the continuous efforts of synthetic chemists to prepare materials with enhanced luminescent properties and processabilities. This article provides a review of the main types of organic materials that have been used in the fabrica‐tion of light‐emitting diodes either as emitting materials or as charge‐transport layers. Special attention will be paid to the different synthetic strategies that have been followed in order to tune the color of the emission, to increase stability of materials and to enhance their processabilities.

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“…This is 10-fold less than the saturation rate of TDI of R ∞ ) k 21 (1 + k isc /k 21 )/(2 + k isc /k T ) ) 82 × 10 6 s, calculated from the transition probabilities given earlier. 18,19 The corresponding binary image of these data (Figure 3d) shows only 57 ( 10 bright spots that exceed onehalf of the maximum intensity in the image (above the background). However, the concentration of dye molecules in the PVB film is 12 ( 6 molecules/µm 2 , and the total number of molecules on the imaged area is 10 000-30 000.…”

Section: Number Of Fluorescing Molecules: Simulation Vs Experimentmentioning

confidence: 99%

“…Here we report on fluorescence bleaching experiments with terrylenediimide (TDI) molecules 18 embedded in a polyvinylbutyral (PVB) polymer film. These dye molecules, excited by a continuous HeNe laser line at 633 nm, allow quantitative analysis of single-molecule fluorescence because of their high photostability and high fluorescence quantum yield.…”

Section: Introductionmentioning

confidence: 99%

Fluorescence Blinking and Photobleaching of Single Terrylenediimide Molecules Studied with a Confocal Microscope

Göhde¹,

Fischer²,

Fuchs³

et al. 1998

J. Phys. Chem. A

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University of Groningen A. Herrmann and K. Mu 1llenMax-Planck-Institut für Polymerforschung, D-55128 Mainz, Germany ReceiVed: April 16, 1998; In Final Form: June 9, 1998 Single terrylenediimide molecules diluted in a 20-nm-thick polyvinylbutyral polymer film were localized and observed by scanning confocal fluorescence microscopy. A modular and compact confocal microscope and the high optical stability of the molecules allowed a repeated imaging and observation over >5 h at room temperature. Most of the molecules showed several "on-off-on" transitions (blinking) on a time scale from seconds to hours, before permanent bleaching occurred. We determined that >1.5 × 10 7 fluorescence photons are emitted from the most-stable molecules before the final bleaching step occurs. Despite the "onoff-on" transitions, however, the overall change in fluorescence intensity, either integrated over each image of a time series or summed for several individual molecules, resembled an exponential-like decay, familiar from measurements of many-molecule ensembles. We also observed the polarization of the fluorescence from single molecules during excitation with circular polarized light. From these measurements, possible rotations of the molecular dipoles were studied. Over a span of 5 h, the polarization angle in most cases did not change by >15-20°. This may explain the slow and small intensity changes but excludes molecular rotation as a reason for the blinking behavior.

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Terrylenimides: New NIR Fluorescent Dyes

Cited by 197 publications

References 27 publications

Perylene Imides for Organic Photovoltaics: Yesterday, Today, and Tomorrow

Perylene Imides for Organic Photovoltaics: Yesterday, Today, and Tomorrow

The chemistry of electroluminescent organic materials

Fluorescence Blinking and Photobleaching of Single Terrylenediimide Molecules Studied with a Confocal Microscope

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