Modular Synthesis of Aromatic Hydrocarbon Macrocycles for Simplified, Single-Layer Organic Light-Emitting Devices

Ikemoto, Koki; Yoshii, Asami; Izumi, Takako; Taka, Hideo; Kita, Hiroshi; Xue, Jing Yang; Kobayashi, Ryo; Sato, Sota; Isobe, Hiroyuki

doi:10.1021/acs.joc.5b02620

Cited by 46 publications

(44 citation statements)

References 24 publications

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“…6 Pristine aromatic hydrocarbons were recently revisited by introducing a macrocyclization strategy toward the molecular design of organic light-emitting device (OLED) materials, and macrocyclic aromatic hydrocarbons (MAHs) were thus established as promising and unique materials for OLEDs. [7][8][9][10][11] One of the interesting features of the OLEDs with MAH such as [n]cyclo-meta-phenylene ([n]CMP, n = 5, 6) is their simple architecture. 11 Most of the conventional OLEDs are composed of several layers, such as a hole-transport layer, electron-transport layer, and hole-blocking layer, in addition to an emission layer.…”

Section: All Article Content Except Where Otherwise Noted Is Licensmentioning

confidence: 99%

Magneto-electroluminescence effects in the single-layer organic light-emitting devices with macrocyclic aromatic hydrocarbons

et al. 2018

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Section: All Article Content Except Where Otherwise Noted Is Licensmentioning

confidence: 99%

Magneto-electroluminescence effects in the single-layer organic light-emitting devices with macrocyclic aromatic hydrocarbons

et al. 2018

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“…Residual materials were subjected to a preparative HPLC separation with a Cosmosil πNAP column (20ϕ×250 mm; eluent of 50 % CHCl 3 /MeOH) to afford [8]CPhen 3,6 as a white powder in 0.3 % yield (6.13 mg, 5.26 mmol; NMR=89.5 wt % purity). As was the case with our previous macrocycles, residual contaminants such as water and chloroform could not be removed completely, and the yields were obtained after quantification by combustion elemental analysis or NMR analysis by using an internal standard of bromoform.…”

Section: Methodsmentioning

confidence: 99%

“…The precipitates were dissolved in boiling oDCB (650mL), filtered by hot filtration, and recrystallization to afford [8]CPhen 3,6 as aw hite powder in 0.3 % yield (6.13 mg, 5.26 mmol;N MR = 89.5 wt %p urity). As was the case with our previous macrocycles, [3,19] residual contaminants such as water and chloroform could not be removed completely,a nd the yields were obtained after quantification by combustion elemental analysis or NMR analysis by using an internal standard of bromoform. The purity was quantified to be 89.5 wt %b yq uantitative 1 HNMR analysis by using an internal standard (CHBr 3 ).…”

Section: Experimental Section Materialsmentioning

confidence: 99%

[n]Cyclo‐3,6‐phenanthrenylenes: Synthesis, Structure, and Fluorescence

Tian

Ikemoto

Sato

et al. 2017

Chemistry An Asian Journal

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Five congeners of [n]cyclo-3,6-phenanthrenylene with 3, 4, 5, 7, and 8 panels were obtained from one-pot macrocyclization of dibromophenanthrene, and their crystal structures with diverse molecular shapes were revealed by X-ray crystallography. The compounds, except the four-panel congener, were highly fluorescent in solution, with quantum yields up to 85 %. The least fluorescent four-panel congener showed the smallest change in its absorption spectrum from that of monomeric phenanthrene, which provided an interesting structure-activity relationship for fluorescent macrocycles to guide future studies.

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“…12,13 In this study, we envisioned the periphery modification for electronic tuning of OLED materials and designed a donor/acceptor conjugate of [6]CMP. Among two synthesis routes examined, a homo-coupling route via [3 + 3] assembly of phenylene panels was found superior to a [1 + 2 + 1 + 2] cross-coupling route.…”

mentioning

confidence: 99%

“…10,11 After revealing a bipolar charge carrier transport ability of the unsubstituted [n]CMP, 9 we introduced bulky substituents at the macrocyclic periphery to find multirole hydrocarbon materials for highly efficient single-layer OLEDs. 12,13 In this study, we envisioned the periphery modification for electronic tuning of OLED materials and designed a donor/acceptor conjugate of [6]CMP. Among two synthesis routes examined, a homo-coupling route via [3 + 3] assembly of phenylene panels was found superior to a [1 + 2 + 1 + 2] cross-coupling route.…”

mentioning

confidence: 99%

Communication—Structural Modulation of Macrocyclic Materials for Charge Carrier Transport Layers in Organic Light-Emitting Devices

Yoshii

Ikemoto

Izumi

et al. 2017

ECS J. Solid State Sci. Technol.

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A cyclo-meta-phenylene (CMP) macrocycle with donor/acceptor substituents was designed. After optimization of the synthesis routes, the CMP congener was synthesized via [3 + 3] assembly of phenylene panels in moderate yield. The molecule showed a highly crystalline nature, and a single crystal formed upon sublimation. The molecule was transparent in the visible light region and was thermally robust with a decomposition temperature of 583 • C. The effect of the donor/acceptor substituents was evaluated for charge carrier transport layers in emitter-doped phosphorescent OLEDs, which showed a dramatic improvement in its electron transporting ability as well as power efficiency in devices. Structural modification is one of the most intriguing potentials of organic materials. Integration of requisite characteristics via structural modification often holds a key role for the development of promising materials from a privileged core structure.1 Through our investigations on nanocarbon-inspired molecules, 2-4 we have casted a spotlight on arylene macrocycles as organic electronic materials.5-8 Thus, a series of macrocyclic hydrocarbons, in particular, [n]cyclo-meta-phenylenes (CMPs; Figure 1) 9 revealed unique potentials of their cyclic π-systems to be embedded in organic light-emitting devices (OLEDs).10,11 After revealing a bipolar charge carrier transport ability of the unsubstituted [n]CMP, 9 we introduced bulky substituents at the macrocyclic periphery to find multirole hydrocarbon materials for highly efficient single-layer OLEDs. 12,13 In this study, we envisioned the periphery modification for electronic tuning of OLED materials and designed a donor/acceptor conjugate of [6]CMP. Among two synthesis routes examined, a homo-coupling route via [3 + 3] assembly of phenylene panels was found superior to a [1 + 2 + 1 + 2] cross-coupling route. The electronic tuning with donor/acceptor substituents resulted in a highly crystalline nature of the CMP congener and in improvements of the performances in OLEDs. Experimental Synthesis of 3:A mixture of bis(1,5-cyclooctadiene)nickel(0) (2.48 g, 9.02 mmol), 2,2'-bipyridyl (1.41 g, 9.03 mmol), 1,5-cyclooctadiene (1.11 ml, 9.05 mmol), DMF (150 mL) and toluene (150 mL) was stirred at room temperature for 30 minutes. The precursor terphenyl 6 was stirred in toluene (601 mL) at 80• C, and to this solution was added the solution of Ni complex. After 1 h, 1 M HCl (50 mL) was added, and the mixture was stirred for 3 h. Precipitates were removed by filtration, and the filtrate was extracted with toluene (500 mL × 3). Combined organic solution was dried over MgSO 4 to afford a crude material after removal of volatile materials. The crude material was washed with CHCl 3 (80 mL) and was recrystallized from nitrobenzene to give 3 in 20% yield (417 mg, 0.446 mmol). For the device application, the solid was further purified by sublimation.z E-mail: satosota@m.tohoku.ac.jp; isobe@m.tohoku.ac.jpOLEDs were fabricated and evaluated by using methods reported in previous studies. 4, 140.3, 140.2, ...

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Modular Synthesis of Aromatic Hydrocarbon Macrocycles for Simplified, Single-Layer Organic Light-Emitting Devices

Cited by 46 publications

References 24 publications

Magneto-electroluminescence effects in the single-layer organic light-emitting devices with macrocyclic aromatic hydrocarbons

Magneto-electroluminescence effects in the single-layer organic light-emitting devices with macrocyclic aromatic hydrocarbons

[n]Cyclo‐3,6‐phenanthrenylenes: Synthesis, Structure, and Fluorescence

Communication—Structural Modulation of Macrocyclic Materials for Charge Carrier Transport Layers in Organic Light-Emitting Devices

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