ChemInform Abstract: AROMATICITY IN BRIDGED HETEROANNULENES

Jurić, Albin; Sabljic, A.; Trinajstić, Nenad

doi:10.1002/chin.198449372

Cited by 3 publications

(4 citation statements)

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“…These difference and similarity can be qualitatively understood by their aromatictiy and effectiveness of π-delocalization over the naphthodichalcogenophene cores. Furan is known as the least aromatic among the present three heteroaromatics, indicating its poor conjugation nature. This can lead to the least effective π-delocalization over the entire 18-π electron system of 5a core, resulting in the blue-shifted absorption band among the three compounds.…”

Section: Resultsmentioning

confidence: 99%

Naphtho[2,3-b:6,7-b′]dichalcogenophenes: Syntheses, Characterizations, and Chalcogene Atom Effects on Organic Field-Effect Transistor and Organic Photovoltaic Devices

et al. 2011

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New linear-shaped naphtho[2,3-b:6,7-b′]-difurans (NDFs) and -selenophenes (NDSs) were synthesized selectively from 3,7-dibromo-2,6-dihydroxynaphthalene and evaluated as organic semiconductors in comparison to corresponding naphtho[2,3-b:6,7-b′]dithiophenes (NDTs). Evaluation of the electronic structures of the parent compounds by means of electrochemical and optical measurements clearly indicated that NDT and NDS are quite similar to each other, whereas only NDF has a marked different electronic structure. Thin film devices, including organic field-effect transistors (OFETs) and bilayer photovoltaics (OPVs) with C 60 or C 70 as an acceptor layer, were fabricated with the diphenyl derivatives using vacuum deposition. The thin films were found to be nicely crystalline with the edge-on molecular orientation both on Si/SiO 2 (for OFETs) and ITO substrates (for OPVs). The thin films acted as active semiconducting layer in OFETs with mobility higher than 0.1 cm 2 V −1 s −1 and as a donor layer in OPVs with power conversion efficiencies of up to 2.0%, indicating that the present naphthodichalcogenophenes are potential core structures for the development of new organic semiconductors.

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Section: Resultsmentioning

confidence: 99%

Naphtho[2,3-b:6,7-b′]dichalcogenophenes: Syntheses, Characterizations, and Chalcogene Atom Effects on Organic Field-Effect Transistor and Organic Photovoltaic Devices

et al. 2011

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“…5 On the other hand, relatively lower aromaticity of furan than thiophene and pyrrole may give rise to different electronic properties in the resulting furan-based materials. 6 In fact, we have recently reported a series of diphenyl-naphtho[2,3-b;5,6-b 0 ]dichalcogenophenes (1-3, Fig. 1) and revealed that 1 is a fairly stable compound likely owing to the fused-furan structure, and furthermore, the lower aromaticity of the fused-furan rings in 1 affords distinct molecular properties, e.g., oxidation potential (or ionization potential, IP, at the thin film state) and absorption/emission properties, from those of the thiophene-(2) or selenophene counterparts (3).…”

mentioning

confidence: 99%

[2,2′]Bi[naphtho[2,3-b]furanyl]: a versatile organic semiconductor with a furan–furan junction

et al. 2012

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“…For example, furan serves as a diene in the [4+2] Diels-Alder reactions under milder conditions than those for thiophene and pyrrole 67 . On the other hand, the relatively lower aromaticity of furan compared to those of thiophene and pyrrole may give rise to different electronic properties in the resulting furan-based materials 68 .…”

Section: Introductionmentioning

confidence: 99%

“…67 On the other hand, the relatively low aromaticity of furan compared to those of thiophene and pyrrole may give rise to different electronic properties in the resulting furan-based materials. 68 Over the last decade, highly efficient blue OLEDs have attracted considerable attention due to their potential applications in full color ultra-thin flat panel displays. [69][70][71][72][73][74][75] Organic light sources are currently made from either low molecular weight organic materials or polymers.…”

Section: Introductionmentioning

confidence: 99%

The optical properties and quantum chemical calculations of thienyl and furyl derivatives of pyrene

Idzik

Cywiński

Kuźnik

et al. 2015

Phys. Chem. Chem. Phys.

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A detailed electrochemical, photophysical and theoretical study is presented for various new thienyl and furyl derivatives of pyrene. Their optical properties are described based on UV-VIS absorption and both steady-state and time-resolved fluorescence spectroscopy. DFT and TDDFT calculations are also presented to support experimental data. The calculations results show that HOMO-LUMO orbitals are delocalized uniformly between aromatic core and aryl substituents. Good electrochemical stability of thienyl and furyl hybrids of pyrene confirm their potential application for light emitting electrochemical cells or spintronics mainly due to their beneficial optical and charge transport properties in electrochromic devices. In order to demonstrate this potential, an OLED device is presented. Synthesized compounds included in this OLED device both facilitate electron transport and act as a light emitting layer.

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ChemInform Abstract: AROMATICITY IN BRIDGED HETEROANNULENES

Cited by 3 publications

References 1 publication

Naphtho[2,3-b:6,7-b′]dichalcogenophenes: Syntheses, Characterizations, and Chalcogene Atom Effects on Organic Field-Effect Transistor and Organic Photovoltaic Devices

Naphtho[2,3-b:6,7-b′]dichalcogenophenes: Syntheses, Characterizations, and Chalcogene Atom Effects on Organic Field-Effect Transistor and Organic Photovoltaic Devices

[2,2′]Bi[naphtho[2,3-b]furanyl]: a versatile organic semiconductor with a furan–furan junction

The optical properties and quantum chemical calculations of thienyl and furyl derivatives of pyrene

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