<i>meso</i>
            ‐Benzdianthron (Helianthron),
            <i>meso</i>
            ‐Naphthodianthron, und ein neuer Weg zum Flavanthren

Schöll, Roland; Mansfeld, J.

doi:10.1002/cber.19100430288

Cited by 184 publications

(109 citation statements)

References 10 publications

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“…As shown in Figure 8, the UV/Vis absorptions pectrumo f3b exhibits ab and that is characteristic of acenes in the visible-light region. The fluorescences pectra of 3b exhibits aS tokes shift of 15 nm, which is smaller than those of twisted-and anti-2b, suggesting the twistacene backboneo f3b is more rigid than those of 2b.T he cyclic voltammogram of 3b in CH 2 ure S6 in the Supporting Information) exhibits two reversible oxidation waves with the half-wavep otential at 0.31 and 0.60 Vv ersus ferrocenium/ferrocene. From the first oxidation potential, the HOMO energy level of 3b is estimated as À5.41 eV.…”

Section: Structure and Properties Of 3bmentioning

confidence: 99%

Twisted Polycyclic Arenes from Tetranaphthyldiphenylbenzenes by Controlling the Scholl Reaction with Substituents

Yong

Yuan

Shan

et al. 2016

Chemistry A European J

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Herein, we report two new types of twisted polycyclic arenes (2 a, b and 3 a, b) with constitutionally isomeric π-backbones, which are synthesized by controlling the Scholl reaction of 1,2,4,5-tetra(naphth-2-yl)-3,6-diphenylbenzene (1) with properly positioned electron-donating substituents. With a polycyclic backbone containing two [5]helicene and four [4]helicene moieties, 2 a and b are new members of multiple helicenes with interesting stereochemistries. The as-synthesized 2 a and b are the twisted isomers, and thermal isomerization of twisted-2 b results in anti-2 b, a more stable stereoisomer. Both twisted- and anti-2 b have been fully characterized, and the thermal isomerization of twisted-2 b has been studied with H NMR spectroscopy and DFT calculations. Compounds 3 a and b are new members of twistacenes, the benzannulated pentacene backbone of which exhibits an end-to-end twist as found from the crystal structure. Twisted- and anti-2 b are also found to function as p-type semiconductors in solution-processed thin film transistors, whereas the thin films of 3 b appear insulating presumably due to the lack of π-π interactions.

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Section: Structure and Properties Of 3bmentioning

confidence: 99%

Twisted Polycyclic Arenes from Tetranaphthyldiphenylbenzenes by Controlling the Scholl Reaction with Substituents

Yong

Yuan

Shan

et al. 2016

Chemistry A European J

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“…Known for a century, Scholl-type reactions allow the synthesis of the perylene core by a coupling reaction between two naphthyl fragments and an oxidant, which also acts as a Lewis acid. [14] The first route (Scheme 3) began with a double Knoevenagel reaction between acenaphthenequinone and diethyl acetonedicarboxylate under basic conditions (Scheme 3). [16] Triethylamine was used as a base to avoid any hydrolysis of the ester groups.…”

Section: Resultsmentioning

confidence: 99%

“…Two synthetic routes were considered for the formation of the chassis: The first strategy involved a Scholl oxidative coupling reaction, [14] which would allow the formation of the perylene core in one step from compound 1. On the contrary, the second route would form the perylene core in two steps from compound 2.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Polycyclic Aromatic Hydrocarbon‐Based Nanovehicles Equipped with Triptycene Wheels

Rouville

Garbage

Cook

et al. 2012

Chemistry A European J

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Two new nanovehicles that have extended aromatic platforms as the cargo zones have been obtained. Two strategies were considered for the formation of the perylene core from two naphthalene precursors. The first was based on a Scholl-type reaction involving an oxidant, and the second used a brominated derivative to perform a homocoupling reaction. The first strategy failed under diverse coupling conditions in the presence of several strong oxidants. Nevertheless, the use of CoF(3) in trifluoroacetic acid triggered a dimerization reaction between two ester groups of one molecule and the naphthalene unit of another, thereby surprisingly yielding a ten-membered carbon macrocycle. The second strategy encountered a lack of reactivity of the substrate under several homocoupling conditions. The dimerization was not easily performed but Ullmann-type conditions ultimately gave the expected product. The low yield and low solubility of the product encouraged us to modify our initial design. The synthesis of a new chassis that incorporated additional tert-butyl groups improved the solubility of the molecules and also prevented overcyclization of the aromatic platform by blocking these positions. Some p-phenylene spacers were also intercalated between the iodine and perylene centers to increase the reactivity of the halide towards coupling reactions. Two new chassis were obtained by Scholl-type oxidative coupling using FeCl(3) as the oxidant. The introduction of four triptycene wheels allowed the formation of the two corresponding nanovehicles.

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“…From all synthetic approaches to HBCs that have been developed during the last century, the oxidative aryl-aryl coupling under the influence of Lewis acids, or Scholl reaction, remains the crucial step [20,21]. Early procedures using NaCl/AlCl 3 limited the scope of the cyclodehydrogenation reaction owing to its harsh conditions.…”

Section: Synthesis Of Hbc and Its Derivativesmentioning

confidence: 99%

Hexa-peri-hexabenzocoronene in organic electronics

Seyler

Purushothaman

Jones

et al. 2012

Pure and Applied Chemistry

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Polycyclic aromatic hydrocarbons (PAHs) are in a class of functional organic compounds with increasing importance in organic electronics. Their tunable photophysical properties and typically strong intermolecular associations make them ideal materials in applications where control of charge mobility is essential. Hexa-peri-hexabenzocoronene (HBC) is a disc-shaped PAH that self-associates into columnar stacks through strong π-π interactions. By decorating the periphery of the HBC molecule with various substituents, a range of properties and functions can be obtained including solution processability, liquid crystallinity, and semiconductivity. In this review article, the synthesis, properties, and functions of HBC derivatives are presented with focus on work published in the last five years.

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meso ‐Benzdianthron (Helianthron), meso ‐Naphthodianthron, und ein neuer Weg zum Flavanthren

Cited by 184 publications

References 10 publications

Twisted Polycyclic Arenes from Tetranaphthyldiphenylbenzenes by Controlling the Scholl Reaction with Substituents

Twisted Polycyclic Arenes from Tetranaphthyldiphenylbenzenes by Controlling the Scholl Reaction with Substituents

Synthesis of Polycyclic Aromatic Hydrocarbon‐Based Nanovehicles Equipped with Triptycene Wheels

Hexa-peri-hexabenzocoronene in organic electronics

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