Diels–Alder Cycloaddition of Tetraphenylcyclopentadienone and 1,3,5‐Hexatriynes

Sale, Anna Chiara; Murray, Adrian H.; Prenzel, Dominik; Hampel, Frank; Luca, Lidia De; Tykwinski, Rik R.

doi:10.1002/ejoc.201600116

Cited by 6 publications

(3 citation statements)

References 52 publications

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“…The reactivity pattern of such compounds was explored in two main categories: (1) cycloaddition reactions or (2) the formation of metal complexes. An example of the first one is shown in a very recent report by Tykwinski and co-workers which showed regioselective addition of tetraphenylcyclopentadienone to hexatriynes where the selectivity was achieved by the use of bulky end-groups. Previously, Diederich and co-workers presented a very elegant example of regioselectivity switching during TCNE (tetracyanoethylene) and TCNQ (tetracyanoquinodimethane) additions , as well as controlled multiple addition of TCNE and TTF (tetrathiafulvalene) to polyynes .…”

Section: Introductionmentioning

confidence: 99%

Polyynes as Precursors of Photoluminescent Solvent Polarity Probes

Pigulski

Cichos

Szafert

2017

ACS Sustainable Chem. Eng.

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A simple and convenient synthesis of substituted thiophenes from pyrrole end-capped polyynes is being reported. The method allows one to obtain a variety of different fluorescent oligo(hetero)aryles from polyyne precursors. The resulting thiophenes exhibit strong emission solvatochromism in a wide scope of different solvents which makes them promising candidates for fluorescent solvent polarity probes.

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Section: Introductionmentioning

confidence: 99%

Polyynes as Precursors of Photoluminescent Solvent Polarity Probes

Pigulski

Cichos

Szafert

2017

ACS Sustainable Chem. Eng.

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“…Sale et al, used the Diels–Alder cycloaddition reactions of 1,3,5-hexatriynes with tetraphenylcyclopentadienone as a crucial step for the synthesis of 1,4-bis[(hexasubstituted)phenyl]-1,3-butadiynes ( Scheme 203 ) [ 254 ].…”

Section: Cyclopentadienones For the Multisubstituted Benzene Ring And Naphthalene System Formationmentioning

confidence: 99%

“… DA cycloaddition of tetraphenylcyclopentadienone and 1,6-disubstituted-1,3,5-hexatriynes as an initial step in the syntheses of 1,4-bis[(tetraphenyl-arylethynyl)phenyl]-1,3-butadiynes [ 254 ]. Reagents and conditions: R 1 , R 2 = Si i Pr 3 , Si i Pr 3 ; Si i Pr 3 , SiMe 3 and others; a = thermal (250 °C in dichlorobenzenes) or MW (210 °C in xylene) conditions; b = next steps.…”

Section: Figure and Schemesmentioning

confidence: 99%

Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry

et al. 2021

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Phenyl, naphthyl, polyarylphenyl, coronene, and other aromatic and polyaromatic moieties primarily influence the final materials’ properties. One of the synthetic tools used to implement (hetero)aromatic moieties into final structures is Diels–Alder cycloaddition (DAC), typically combined with Scholl dehydrocondensation. Substituted 2-pyranones, 1,1-dioxothiophenes, and, especially, 1,3-cyclopentadienones are valuable substrates for [4 + 2] cycloaddition, leading to multisubstituted derivatives of benzene, naphthalene, and other aromatics. Cycloadditions of dienes can be carried out with extrusion of carbon dioxide, carbon oxide, or sulphur dioxide. When pyranones, dioxothiophenes, or cyclopentadienones and DA cycloaddition are aided with acetylenes including masked ones, conjugated or isolated diynes, or polyynes and arynes, aromatic systems are obtained. This review covers the development and the current state of knowledge regarding thermal DA cycloaddition of dienes mentioned above and dienophiles leading to (hetero)aromatics via CO, CO2, or SO2 extrusion. Particular attention was paid to the role that introduced aromatic moieties play in designing molecular structures with expected properties. Undoubtedly, the DAC variants described in this review, combined with other modern synthetic tools, constitute a convenient and efficient way of obtaining functionalized nanomaterials, continually showing the potential to impact materials sciences and new technologies in the nearest future.

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Aromaticity‐Dependent Memristive Switching

Cechosz,

Alluhaibi,

Mazur

et al. 2024

Adv Elect Materials

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In recent years, memristors have drawn attention as non‐volatile memory devices for advanced computing engineering. The features of memristors, such as hysteresis, high resistance state to low resistance state ratio, retention time, etc., are determined by the material, structure of the device, the switching mechanism, and the kinetics resulting from the characteristics of the materials. Here, a resistive switching is proposed based on the aromaticity change of the material. A device has been built based on tetracyclone that undergoes the transition from an antiaromatic to an aromatic state upon applied potential. This phenomenon results in the presence of two distinguishable, and more importantly, stable resistive states of the memristor. On the basis of theoretical and experimental investigation, it is demonstrated that the working principle of the device depends on the redox change of the molecules. This study provides the foundation for a new kind of memristive switching mechanism: the formation of virtual conductivity paths. They can be a key to improving the performance of semiconductor memory devices in crucial factors such as stability, reversibility, and nonvolatility because these paths are related to electron delocalization and do not involve any significant structural changes in the device (e.g., diffusion).

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Diels–Alder Cycloaddition of Tetraphenylcyclopentadienone and 1,3,5‐Hexatriynes

Cited by 6 publications

References 52 publications

Polyynes as Precursors of Photoluminescent Solvent Polarity Probes

Polyynes as Precursors of Photoluminescent Solvent Polarity Probes

Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry

Aromaticity‐Dependent Memristive Switching

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