Facile synthesis of terrylene and its isomer benzoindenoperylene

Avlasevich, Yuri; Kohl, Christopher; Müllen, Kläus

doi:10.1039/b516264e

Cited by 64 publications

(53 citation statements)

References 29 publications

(57 reference statements)

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“…The extension of the aromatic p-system along the molecular long axis does not only cause a bathochromic shift, which allows maxima of absorption from 580 to 950 nm, but also increases their absorption coefficients. [100,101] The particularity of the perylene dyes is that they offer the introduction of a diverse set of substituents at different positions within the chromophore scaffold. In this way, they can be decorated in the bay or in the peri positions (Fig.…”

Section: Perylene Dyes For Solar Cell Devicesmentioning

confidence: 99%

Polyphenylene‐Based Materials: Control of the Electronic Function by Molecular and Supramolecular Complexity

2009

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Organic electronics is one of the hottest and most exciting research topics today. However, its performance still lags behind that of inorganic‐based electronics. This Progress Report demonstrates that by controlling the complexity of organic molecules at the molecular and at the supramolecular level as well as by choosing suitable processing techniques, the desired function for applications in electronics can be achieved. Our main focus is on polyphenylene‐based nanomaterials, versatile organic molecules that allow access to novel intricate materials. We emphasize the molecular complexity as well as the supramolecular organization and the interfacing of novel organic materials as key guidelines.

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Section: Perylene Dyes For Solar Cell Devicesmentioning

confidence: 99%

Polyphenylene‐Based Materials: Control of the Electronic Function by Molecular and Supramolecular Complexity

2009

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“…6) also supports the existence of relatively open PAH structures. A massive presence of extended aromatic structures in the dimer-rich vs. the monomer-rich PFs would drastically shift the absorption of visible light to higher wavelengths [24]. However, the "red shift", although observable, is relatively small.…”

Section: Analytical and Structural Characterization Of Dimer-rich Pitmentioning

confidence: 97%

The Molecular Design of High-Performance Carbon Materials

Thies¹

2008

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“…Stirring a solution of compound 3 in anhydrous toluene with potassium in air (rather than argon) resulted in the formation of product 4 in astonishingly high yield (52 %; Several dehydrogenative coupling reactions have led to benzo[j]fluoranthene-type structures, rather than products that contain a rylene moiety. [41] Therefore, scrupulous structural identification and assignment were achieved by using 1D NMR ( 1 H and 13 C NMR) and 2D NMR spectroscopy (gCOSY, NOESY, HSQCAD, and IMPACT_gHMBCAD). In particular, COSY analysis allowed us to distinguish between two possible structures, because they possessed differ-ent NMR spin systems.…”

Section: Introductionmentioning

confidence: 99%

Vertically π‐Expanded Imidazo[1,2‐a]pyridine: The Missing Link of the Puzzle

Firmansyah

Banasiewicz

Deperasińska

et al. 2014

Chemistry An Asian Journal

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The dehydrogenative coupling of imidazo[1,2-a]pyridine derivative has been achieved for the first time. In cases in which the most-electron-rich position of the electron-excessive heterocycle was blocked by a naphthalen-1-yl substituent, neither oxidative aromatic coupling nor reaction under Scholl conditions enabled the fusion of the rings. The only method that converted the substrate into the corresponding imidazo[5,1,2-de]naphtho[1,8-ab]quinolizine was coupling in the presence of potassium in anhydrous toluene. Moreover, we discovered new, excellent conditions for this anion-radical coupling reaction, which employed dry O2 from the start in the reaction mixture. This method afforded vertically fused imidazo[1,2-a]pyridine in 63% yield. Interestingly, whereas the fluorescence quantum yield (Φ(fl)) of compound 3, despite the freedom of rotation, was close to 50%, the Φ(fl) value of flat naphthalene-imidazo[1,2-a]pyridine was only 5%. Detailed analysis of this compound by using DFT calculations and a low-temperature Shpol'skii matrix revealed phosphorescence emission, thus indicating that efficient intersystem-crossing from the lowest-excited S1 level to the triplet manifold was the competing process with fluorescence.

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Facile synthesis of terrylene and its isomer benzoindenoperylene

Cited by 64 publications

References 29 publications

Polyphenylene‐Based Materials: Control of the Electronic Function by Molecular and Supramolecular Complexity

Polyphenylene‐Based Materials: Control of the Electronic Function by Molecular and Supramolecular Complexity

The Molecular Design of High-Performance Carbon Materials

Vertically π‐Expanded Imidazo[1,2‐a]pyridine: The Missing Link of the Puzzle

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