Benzofuran-fused Phosphole: Synthesis, Electronic, and Electroluminescence Properties

Chen, Hui; Delaunay, Wylliam; Li, Jing; Wang, Zuoyong; Bouit, Pierre‐Antoine; Tondelier, Denis; Geffroy, Bernard; Mathey, François; Duan, Zheng; Réau, Régis; Hissler, Muriel

doi:10.1021/ol303260d

Cited by 96 publications

(40 citation statements)

References 37 publications

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“…The most straightforward synthetic route to furan-silole ladder compounds may be the reaction of the dimetalated dibenzofuran with R 2 SiCl 2 (Scheme 1), a similar procedure was reported for the synthesis of dibenzofuran-fused phosphole [40]. Effectively, the treatment of iodo-substituted benzofuran 1 with two equivalents of nBuLi produces the corresponding dianion, which was then quenched with Me 2 SiCl 2 at −78 • C leading to compound 2 in moderate yield (26%).…”

Section: Resultsmentioning

confidence: 96%

“…However, planar molecules can be used as emitters in OLEDs if an efficient control of the packing of these planar structures in solid state is achieved, allowing to restore their emissive properties. For example, we recently reported on the preparation of ladder-benzofuran fused phospholes C (Figure 1) showing efficient electroluminescent properties in OLEDs if the compound C is diluted in a 4,4′-bis(2,2-diphenylvinyl)-1,1′-biphenyl (DPVBi) matrix [40]. Since Si-containing planar-π-conjugated systems ( Figure 1B) and benzofuran fused-π-conjugated systems ( Figure 1C) are highly efficient emitters, we decided to develop and study the properties of Si,O-ladder π-conjugated systems (Scheme 1) as potential efficient fluorescent emitters in OLEDs.…”

Section: Methodsmentioning

confidence: 99%

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Blue Electrofluorescence Properties of Furan–Silole Ladder Pi-Conjugated Systems

et al. 2018

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Abstract:A synthetic route to novel benzofuran fused silole derivatives is described and the new compounds were fully characterized. These compounds showed optical and electrochemical properties that differ from their benzothiophene analog. Preliminary results show that these derivatives can be used as blue emitters in organic light emitting devices (OLEDs) illustrating the potential of these new compounds for opto-electronic applications.

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Section: Resultsmentioning

confidence: 96%

Section: Methodsmentioning

confidence: 99%

Blue Electrofluorescence Properties of Furan–Silole Ladder Pi-Conjugated Systems

et al. 2018

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“…17 −20 For example, incorporation of phospholes into conjugated materials allows fine tuning of their photophysical properties due to modifications on the phosphorus atom. 18,21,22 The complexation of phospholes with metal carbonyls results in structural motifs with one or more transition-metal atoms coordinated by the phosphole unit. 23−25 Thereby, reactions of phospholes with chromium, molybdenum, tungsten, and iron carbonyls are best studied, whereby the metal fragment is coordinated by the phosphorus atom and/or the dienic system.…”

Section: ■ Introductionmentioning

confidence: 99%

Transition-Metal Carbonyl Complexes of 2,5-Diferrocenyl-1-phenyl-1H-phosphole

et al. 2015

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Pentacarbonyl(2,5-diferrocenyl-1-phenyl-1H-phosphole)metal complexes 3a−c (3a, M = Cr; 3b, M = Mo; 3c, M = W) have successfully been synthesized by the reaction of 2,5-diferrocenyl-1-phenyl-1H-phosphole (1) with M-(CO) 5 (thf) (2a, M = Cr; 2b, M = Mo; 2c, M = W). Further irradiation of 3a−c with 1 equiv of 1 in tetrahydrofuran leads to tetracarbonylbis(2,5-diferrocenyl-1-phenyl-1H-phosphole)metal complexes 4a−c (4a, M = Cr; 4b, M = Mo; 4c, M = W). In addition, the reaction of 1 with Fe 2 (CO) 9 gave tetracarbonyl-(2,5-diferrocenyl-1-phenyl-1H-phosphole)iron (6) and heptacarbonyl[μ-(2,3,4,5-η)-1-(2,5-diferrocenyl-1-phenyl-1H-phosphole)]diiron (7), respectively. Treatment of 2,5-diferrocenyl-1-phenyl-1H-phosphole sulfide (8) with Fe 2 (CO) 9 afforded tricarbonyl[(2,3,4,5-η)-(2,5-diferrocenyl-1-phenyl-1H-phosphole 1-sulfide)]iron (9). Complexes 3b,c, 4c, 7, and 9 have been characterized by single-crystal X-ray diffraction. Molecules 3b,c and 4c exhibit a distorted-octahedral geometry, whereas in 4c the two phosphole units are cis-oriented. Coordination of the dienic system to Fe(CO) 3 in 7 and 9, respectively, resulted in a deflection of the phosphorus atom from the C 4 plane. Electrochemical measurements of 3a−c, 4a−c, and 9 demonstrated that the ferrocenyl units can be oxidized separately. The coordination of the dienic system to the Fe(CO) 3 building block leads to a decrease of the redox splitting (ΔE°′ = 190 mV) in comparison to 8 (ΔE°′ = 240 mV). Mixed-valence [3a−c] + , [4a−c] 2+ , and [9] + show IVCT absorptions of weak to moderate strengths. The coordination of the phosphorus atom to M(CO) 5 in 3a−c has no significant influence on the metal−metal interaction in the mixed-valent species. However, the coordination of the dienic system in 9 results in a significantly decreased electronic communication of the Fc/Fc + termini via the heterocyclic core. ■ INTRODUCTIONWithin the series of five-membered heterocycles, especially the phosphorus-containing heterocycles take an exceptional role because they are nonaromatic or only slightly aromatic. 1−6 The pyramidal phosphorus environment and the high inversion barrier of phospholes lead to a hindered interaction of the phosphorus lone pair with the dienic system. 7 This results in a versatile reaction behavior: e.g., phospholes undergo Diels− Alder reactions of the dienic system, oxidation (P III → P V ), or complexation reactions of the phosphorus atom and/or the dienic system. 1,8−12 Due to the low delocalization within the phosphole ring, they typically behave as a classical diene or phosphine. 1 In complexation reactions the metal atoms can be coordinated by the phosphorus atom (two-electron donor), the dienic system (four-electron donor), or both coordination sites (six-electron donor), resulting in the formation of multimetallic compounds. 1,8,13−16 In the development of new materials with promising photophysical properties, phosphorus-based molecules offer the opportunity to modify their features due to their versatile reaction behavior toward numerous trans...

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“…Furan based π-conjugated materials have been attained more interests during the past decade, because furan containing OSMs are more stable and potentially applicable in modern era optoelectronic devices like organic field effect transistor (OFETs), organic solar cells, organic light emitting transistor (OLETs), and organic light-emitting diodes (OLEDs) [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy

et al. 2015

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The present study spotlights the designing of new derivatives of 2,7-bis (4-octylphenyl) naphtho [2,1-b:6,5-b'] difuran (C8-DPNDF) by substituting the alkyl groups (methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl groups) at para position. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods are employed to optimize the molecular structures in ground and first excited states, respectively. Several electro-optical properties including hole/electron reorganization energies (λh/λe), electron affinities (EAs), ionization potentials (IPs), molecular electrostatic potentials (MEP), and frontier molecular orbitals (FMOs) have been evaluated. Furthermore their transfer integrals and intrinsic mobilities values have also been calculated. From this study, it is found that hole mobility of octyl containing derivative is raised to 4.69 cm(2) V(-1) s(-1). Moreover with attaching octyl group, hole transfer integral values have also been enhanced in newly designed derivatives. The balanced hole and electron reorganization energies, and improved transfer integrals lead to enhanced mobility in derivatives with octyl group, highlighting them as an efficient hole transfer material. Unlike the other electro-optical properties, the intrinsic hole mobility has increased because of transfer integral values of octyl containing derivative C8-DPNDF due to the dense and close crystal packing of C8-DPNDF. However, photostability of furan-based materials has not changed by increasing length of extended alkyl chain. Thus our present investigation highlights the importance of alkyl auxiliary groups that are often neglected/replaced with simple methyl group to save computation costs. Graphical Abstract The hole and electron reorganization energies of naphtho[2,1-b:6,5-b']difuran derivatives.

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Benzofuran-fused Phosphole: Synthesis, Electronic, and Electroluminescence Properties

Cited by 96 publications

References 37 publications

Blue Electrofluorescence Properties of Furan–Silole Ladder Pi-Conjugated Systems

Blue Electrofluorescence Properties of Furan–Silole Ladder Pi-Conjugated Systems

Transition-Metal Carbonyl Complexes of 2,5-Diferrocenyl-1-phenyl-1H-phosphole

Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy

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