Tetraceno[2,1,12,11-opqra]tetracene-extended tetrathiafulvalene – redox-controlled generation of a large PAH core

Broman, Søren Lindbæk; Andersen, Cecilie Lindholm; Jousselin‐Oba, Tanguy; Mansø, Mads; Hammerich, Ole; Frigoli, Michel; Nielsen, Mogens Brøndsted

doi:10.1039/c6ob02666d

Cited by 25 publications

(18 citation statements)

References 30 publications

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“…[6b-d] Remarkably, BT 1 is more stable than TIPS-PEN at the beginning of the photo-oxidation process even though its ionization potentiala nd electron affinity are lower.T his result confirms that the stability of the BT scaffold relies on its high degree of aromaticity. [15] The structures of BT 1, BT 2 and BT 3 were confirmed by Xray crystallography (Figure 4). Theoretical calculations of electronic couplings between molecules in interaction were performed using DFT at the PW91/TZP level to evaluatet he potential of these materialst ob eu sed in OFET devices.…”

Section: Resultsmentioning

confidence: 83%

Low Bandgap Bistetracene‐Based Organic Semiconductors Exhibiting Air Stability, High Aromaticity and Mobility

Sbargoud

Mamada

Jousselin‐Oba

et al. 2017

Chemistry A European J

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The benchmark of soluble organic semiconductors based on acenes is the 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS-PEN). However TIPS-PEN still suffers from photoinduced oxidation due to its low degree of aromaticity. Increasing the aromaticity while keeping similar optical and electrochemical properties as well as a shape suitable for good hole transport can be achieved with two-dimensional polycyclic aromatic hydrocarbons (2D-PAHs). Herein, we present an efficient synthesis and characterization of bistetracene derivatives that exhibit a band gap up to 1.71 eV and an increased stability up to 21 times compared to TIPS-PEN and mobility over 0.1 cm V s in solution-processed organic field-effect transistors. Based on simple structural consideration, the high stability is attributed to the aromaticity of the bistetracene which is comparable to an anthrancene along each tetracene. According to Clar's sextet rule, the bistetracene should be best regarded as two anthracenes fused at the face bridged by two ethylenic spacers. The synthesis path paves the way towards the preparation of ambipolar and/or longer 2D-PAHs such as bispentacenes and could give rise to organic semiconductors with interesting properties.

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Section: Resultsmentioning

confidence: 83%

Low Bandgap Bistetracene‐Based Organic Semiconductors Exhibiting Air Stability, High Aromaticity and Mobility

Sbargoud

Mamada

Jousselin‐Oba

et al. 2017

Chemistry A European J

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“…For example, acenes with a buttery structure were originally studied a couple of decades ago, and the buttery structure can be changed to a at structure by electrochemical oxidation. [18][19][20][21] Through precise molecular engineering of the core structure of oligoacenes, Tang and co-workers have shown that quinoidal derivatives of oligoacenes can exhibit aggregation induced restricted intramolecular vibration (RIV). 22,23 AIE is counterintuitive since aggregation tends to quench photoluminescence of organic chromophores.…”

Section: Introductionmentioning

confidence: 99%

The butterfly effect in bisfluorenylidene-based dihydroacenes: aggregation induced emission and spin switching

et al. 2019

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“…Keywords that highlight acene-type PAHs with zig-zag periphery range from singlet fission 17 – 21 , auspicious charge carrier mobilities 22 , 23 , to amplified spontaneous emission 24 , and enlarge the interest in PAHs by the fields of spintronics and molecular magnetism 25 - 27 . Recently, various research groups reported on substituted angularly fused-tetracenes 28 – 32 , which overcome the low stability of linear acenes, by increasing the intrinsic number of Clar’s-sextets 33 . These fused structures showed excellent performances in field-effect transistors 28 , 29 , 31 , 32 .…”

Section: Introductionmentioning

confidence: 99%

Dehydrative π-extension to nanographenes with zig-zag edges

et al. 2018

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Zig-zag nanographenes are promising candidates for the applications in organic electronics due to the electronic properties induced by their periphery. However, the synthetic access to these compounds remains virtually unexplored. There is a lack in efficient and mild strategies origins in the reduced stability, increased reactivity, and low solubility of these compounds. Herein we report a facile access to pristine zig-zag nanographenes, utilizing an acid-promoted intramolecular reductive cyclization of arylaldehydes, and demonstrate a three-step route to nanographenes constituted of angularly fused tetracenes or pentacenes. The mild conditions are scalable to gram quantities and give insoluble nanostructures in close to quantitative yields. The strategy allows the synthesis of elusive low bandgap nanographenes, with values as low as 1.62 eV. Compared to their linear homologues, the structures have an increased stability in the solid-state, even though computational analyses show distinct diradical character. The structures were confirmed by X–ray diffraction or scanning tunneling microscopy.

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Tetraceno[2,1,12,11-opqra]tetracene-extended tetrathiafulvalene – redox-controlled generation of a large PAH core

Abstract: Two tetraceno[2,1,12,11-opqra]tetracene-extended tetrathia-fulvalenes were prepared and found to undergo reversible conversion into their planar polycyclic aromatic hydrocarbons (PAHs) upon electrochemical oxidation - at potentials probing the best valence bond representations.

Cited by 25 publications

References 30 publications

Low Bandgap Bistetracene‐Based Organic Semiconductors Exhibiting Air Stability, High Aromaticity and Mobility

Low Bandgap Bistetracene‐Based Organic Semiconductors Exhibiting Air Stability, High Aromaticity and Mobility

The butterfly effect in bisfluorenylidene-based dihydroacenes: aggregation induced emission and spin switching

Dehydrative π-extension to nanographenes with zig-zag edges

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