2015
DOI: 10.1021/acs.joc.5b02620
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Modular Synthesis of Aromatic Hydrocarbon Macrocycles for Simplified, Single-Layer Organic Light-Emitting Devices

Abstract: A method for the modular synthesis of aromatic hydrocarbon macrocycles has been developed for base materials in single-layer organic light-emitting devices. The method with Ir-catalyzed direct C-H borylation and Suzuki-Miyaura coupling was concise and scalable, which allowed for a gram-scale preparation of aromatic hydrocarbon macrocycles that have bulky substituents at the periphery. The new arylated hydrocarbon macrocycles enabled a quantitative electro-optical conversion in organic light-emitting devices wi… Show more

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Cited by 47 publications
(44 citation statements)
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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%
“…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%
“…Residual materials were subjected to a preparative HPLC separation with a Cosmosil πNAP column (20Ï•Ă—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%
“…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%