Synthesis and Solid-state Optical Properties of 2,3-Dialkyl- and 2,3,8,9-Tetraalkyltetracenes

Kitamura, Chitoshi; Ohara, Takuya; Yoneda, Akio; Kawase, Takeshi; Kobayashi, Takashi; Naito, Hiroyoshi

doi:10.1246/cl.2011.58

Cited by 26 publications

(5 citation statements)

References 11 publications

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“…In contrast to the trisquinones, the tris(tetraceneno)triquinacenes 9 and 10 show the typical structured band shape of higher acenes in the visible region with lowest‐energy transitions at 492 and 512 nm, respectively (Figure 3). The absorption of 9 is close to that of simple 2,3‐dialkyltetracenes 20c. Also, the redshift by Δ$\tilde \nu $ =794 cm −1 for 10 compared with 9 is similar to that reported for 5,12‐diphenyltetracene and parent tetracene (Δ$\tilde \nu $ =770–810 cm −1 , solvent‐depending values) 33a.…”

Section: Resultssupporting

confidence: 77%

Tris(tetraceno)triquinacenes: Synthesis and Photophysical Properties of Threefold Linearly Extended Tribenzotriquinacenes

Mughal

Eberhard

Kuck

2013

Chemistry A European J

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The linear extension of the rigid, C(3v)-symmetrical carbon framework of tribenzotriquinacene (TBTQ) along its three wings is reported. The key step of the extension procedure consists of a Diels-Alder reaction of three ortho-quinodimethane units generated in situ at the triquinacene core. The use of 1,4-naphthoquinone provides a facile and particularly efficient access to tris(tetraceno)-annellated triquinacenes. The steady-state photophysical properties of these new oligotetracenes bearing three mutually orthogonal chomophores are determined and analyzed by DFT calculations.

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Section: Resultssupporting

confidence: 77%

Tris(tetraceno)triquinacenes: Synthesis and Photophysical Properties of Threefold Linearly Extended Tribenzotriquinacenes

Mughal

Eberhard

Kuck

2013

Chemistry A European J

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“…In a previous fluorescence study involving acene, the fluorescence lifetime was observed to increase because the electronic structure of anthracene and its derivatives was changed when a polar substituent group was attached to the anthracene skeleton . However, when a similar electron-donating group of an alkyl chain was attached to a tetracene core, almost no change in the fluorescence yield was observed because the alkyl chain hardly affected the electronic properties of tetracene . Although the (trialkylsilyl)ethynyl groups ( 1b , 1c , and 1d ) exhibited similar absorption spectra and HOMO–LUMO properties, their fluorescence yields were observed to differ.…”

Section: Resultsmentioning

confidence: 91%

Synthesis and Investigation of the Effect of Substitution on the Structure, Physical Properties, and Electrochemical Properties of Anthracenodifuran Derivatives

et al. 2015

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A series of syn/anti mixtures of anthradifuran (ADF) and substituent compounds were systematically synthesized, and the effect of substitution at the 5,11-positions on the neutral and radical states of ADF was investigated. All compounds were measured and analyzed by absorption and fluorescence spectroscopy, cyclic voltammetry, electrochemical absorption spectroscopy, and DFT calculations. The absorption spectra of 5,11-substituent compounds in their neutral state were red-shifted. In addition, the substituted compounds exhibited increased thermal stability with respect to the parent 1a because of elongation of the π-conjugation and an increased steric hindrance effect due to the bulky ethynyl substituent groups. The cyclic voltammograms of all of the compounds exhibited irreversible reduction potentials and irreversible oxidation potentials, except in the case of (trimethylsilyl)silylethynyl-substituted ADF. When the materials were subjected to oxidation/reduction potentials, the radical cation and anion species were generated. The absorption spectra of the radical-cation species of the compounds exhibited similar characteristics and similar absorption ranges (550-1400 nm), whereas the spectra of the radical anion species were blue-shifted (550-850 nm) compared than that of the parent 1a(•-) (550-1100 nm). The DFT computation results suggested that the radical states of lowest energy transitions occurred primarily from π to π(SOMO) or from π(SOMO) to π*.

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“…Symmetric tetraalkyl tetracenes 71i–l were obtained by the reaction of dihydroxynaphthoquinone 68d with thiophenedioxides 90a‐d (Scheme ) . The reduction of the adducts 91 followed by treatment with acetic acid led to the formation of anthraquinones 92 , capable of adding another equivalent of thiophenedioxide forming symmetric tetraalkyltetracenes 71i–l upon reduction and acidic work‐up.…”

Section: Cycloaddition To Carbon–carbon Double Bondmentioning

confidence: 99%

The Diels–Alder Reaction for the Synthesis of Polycyclic Aromatic Compounds

2019

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The Front Cover shows a variety of dienophiles used in the synthesis of functionalized polycyclic aromatic hydrocarbons over the past decade via the Diels‐Alder reaction. Being discovered almost a century ago, this powerful synthetic method can be used for construction of new materials for organic electronics – one of the modern challenges of organic chemistry. Linear or angular, planar or curved, molecular or polymeric – the product scope is vast and will broaden even more with further development of new diene and dienophile components. More information can be found in the Minireview by P. A. Zaikin et al.

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Synthesis and Solid-state Optical Properties of 2,3-Dialkyl- and 2,3,8,9-Tetraalkyltetracenes

Cited by 26 publications

References 11 publications

Tris(tetraceno)triquinacenes: Synthesis and Photophysical Properties of Threefold Linearly Extended Tribenzotriquinacenes

Tris(tetraceno)triquinacenes: Synthesis and Photophysical Properties of Threefold Linearly Extended Tribenzotriquinacenes

Synthesis and Investigation of the Effect of Substitution on the Structure, Physical Properties, and Electrochemical Properties of Anthracenodifuran Derivatives

The Diels–Alder Reaction for the Synthesis of Polycyclic Aromatic Compounds

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