2017
DOI: 10.1246/cl.161015
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Impact of Phenyl Groups on Oxygen-bridged V-shaped Organic Semiconductors

Abstract: We have developed two novel, isomeric compounds of phenyl-substituted dinaphtho [2,3-b:2¤,3¤-d]furan (Ph-DNF-VW and Ph-DNF-VV) using a facile synthetic protocol. Notably, Ph-DNF-VW has been shown to be a strong candidate for lightemitting device applications: it forms a herringbone-packing structure with effective CH£π interactions between phenyl moieties, and exhibits a high thermal stability in the crystal phase in air and a high fluorescence quantum yield in the solid state. Additionally, its carrier mobili… Show more

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Cited by 9 publications
(7 citation statements)
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“…The incorporation of heteroatoms into the carbon skeleton is an excellent tool to adjust and improve the electronic properties of the compounds [5, 6] . In contrast to nitrogen‐ and sulfur‐analogues, [7–9] oxygen heterocycles, for example, containing furan's moiety, have drawn much less attention and became an object of interest only recently [10–19] …”
Section: Figurementioning
confidence: 99%
See 1 more Smart Citation
“…The incorporation of heteroatoms into the carbon skeleton is an excellent tool to adjust and improve the electronic properties of the compounds [5, 6] . In contrast to nitrogen‐ and sulfur‐analogues, [7–9] oxygen heterocycles, for example, containing furan's moiety, have drawn much less attention and became an object of interest only recently [10–19] …”
Section: Figurementioning
confidence: 99%
“…[5,6] In contrast to nitrogen-and sulfur-analogues, [7][8][9] oxygen heterocycles, for example, containing furans moiety, have drawn much less attention and became an object of interest only recently. [10][11][12][13][14][15][16][17][18][19] Among the main reasons for such a late splash of interest are synthetic difficulties connected to lability issues of furans. Meanwhile, a fusion of furan ring(s) to an all-carbon aromatic system appears to be a viable strategy for obtaining stable furan derivatives (also called ladder-type O-bridged heteroacenes [20] ).…”
mentioning
confidence: 99%
“…[ 20 ] Mitsui et al. [ 21 ] reported the impact of phenyl as an end‐group on oxygen‐bridged v‐shaped phenyl substituted dinaphtho[2,3‐ b :2′,3′‐ d ]furan derivative for OFET application. The phenyl substituted compounds resulted in improved physicochemical, thermal, and carrier‐transporting properties than the reported molecules.…”
Section: Introductionmentioning
confidence: 99%
“…[ 23 ] The introduction of the aryl group as an end‐group was found to be advantageous for charge transport and air‐stability in OFET devices. [ 3,24 ] The aryl group can also raise the HOMO level by expanding π ‐conjugation over the system. Further, the role of phenyl, methoxyphenyl, tert ‐butylphenyl, thiophene, and fluorophenyl at the terminal position of the quinoline core were investigated for transistor properties.…”
Section: Introductionmentioning
confidence: 99%
“…Although less π-extended C n –BTBTs exhibit good solubility in common organic solvents at room temperature, they possess relatively deep energy levels of the highest occupied molecular orbital (HOMO) as a p-type OSC, often resulting in large operating voltages in field-effect transistors (FETs) with gold and carbon electrodes. Recently, we also developed conceptually new oxygen- and sulfur-bridged V-shaped binaphthalene π-electron cores (π-cores), dinaphtho­[2,3- b :2′,3′- d ]­furan (DNF–V) and -thiophene (DNT–V) (Figure a). , Both V-shaped derivatives showed (1) high chemical stability under ambient conditions due to deep HOMO levels of <−5.0 eV to resist oxidation by ambient O 2 , (2) suitable solubility in common organic solvents owing to their intramolecular dipole moments (Figure b), (3) high thermal stability without any reactive chemical bonds, and (4) charge carrier mobility equal or superior to currently used amorphous silicon semiconductors (0.5–1.0 cm 2 V –1 s –1 ). Comprehensive studies of their decyl-substituted derivatives, 3,9-didecyldinaphtho­[2,3- b :2′,3′- d ]­furan (C 10 –DNF–VW) and -thiophene (C 10 –DNT–VW), suggested that the central bridging elements and the lateral alkyl side chains conclusively affect their molecular geometries, aggregated structures, and semiconducting properties. ,, Unlike the reported conventional chalcogen-bridged π-cores, V-shaped π-cores form unique bent molecular structures (bent angles between naphthalenes: 3.91–13.9°) in the solid state depending on the bridged elements and substituents (Figure c).…”
Section: Introductionmentioning
confidence: 99%