Convergent synthesis of hexameric naphthylene macrocycles with dicarboxylic imide appendages

Xue, Jing Yang; Nakanishi, Waka; Tanimoto, Daiki; Hara, Daisuke; Nakamura, Yuta; Isobe, Hiroyuki

doi:10.1016/j.tetlet.2013.07.025

Cited by 13 publications

(13 citation statements)

References 17 publications

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“…The single crystal grown during the sublimation allowed us to determine the molecular structure unequivocally by X-ray crystallographic analysis as shown in Figure 2a. The crystal packing of the molecule revealed the presence of trimeric stacks as shown in Figure 2b, 19 which may be the origin of the high crystallinity of 3. Representative properties relevant to optoelectronic applications were investigated.…”

Section: Resultsmentioning

confidence: 96%

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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Section: Resultsmentioning

confidence: 96%

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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“…In 2013, 3,6‐dibromo‐N‐(2,4‐diisopropylphenyl)‐1,8‐naphthalimide (DBDIPPNMI) was firstly synthesized by Hiroyuki et al with the synthetic route shown in Figure …”

Section: Introductionmentioning

confidence: 99%

Conjugated polymers based on 1,8‐naphthalene monoimide with high electron mobility

Zhu

Zhang

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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1,4,8,9‐Naphthalene diimides (NDIs) with strong electron accepting ability and high stability are excellent building blocks for semiconductor polymers. However, 1,8‐naphthalene monoimide (NMI) with similar structure and energy levels as that of NDI has never been used to construct conjugated polymers because of synthetic difficulty. Herein, 3,6‐dibromo‐NMI (DBNMI) with bulky alkyl groups was obtained effectively in a four‐step synthesis, and three donor‐acceptor (D‐A) type conjugated polymers based on NMI were firstly prepared. These polymers have strong absorption in the range of 300–600 nm, low LUMO level of 3.68 eV, and moderate bandgaps of 2.18 eV. Space charge limiting current measurements indicate these polymers are typical electron transporting materials, and the highest electron mobility is up to 5.8 × 10−3 cm2 V−1 s−1, which is close to the star acceptor based on NDI (N2200, 5.0 × 10−3 cm2 V−1 s−1). © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 276–281

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“…Then, the two bromine atoms of 16 were displaced to the corresponding boronic acid pinacol ester (Bpin) using the Miyaura borylation reaction followed by oxidation with hydrogen peroxide. Subsequent benzylation of the resulting hydroxy groups afforded 17 in 71% overall yield for both steps …”

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confidence: 99%

“…Subsequent benzylation of the resulting hydroxy groups afforded 17 in 71% overall yield for both steps. 10 Imide 17 was hydrolyzed to the acid anhydride using potassium hydroxide, 11 and then this was converted to the hydroxyimide, which was further treated with p-toluenesulfonyl chloride to afford the corresponding tosyloxyimide. The tosyloxyimide was smoothly converted to lactam 18 under Lossen rearrangement conditions in 81% overall yield over the three steps from 17.…”

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Total Syntheses of FR-901235, Auxarthrones A–D, and Lamellicolic Anhydride

et al. 2020

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In our previous study, an unusual rearrangement reaction was discovered whereby dinaphthyl ketones with three hydroxy groups at restricted positions were transformed into a phenalenone ring and a benzene ring. Using the rearrangement as a key reaction, the first total syntheses of FR-901235 and auxarthrones A–D from an unstable triketone common intermediate are described. Furthermore, lamellicolic anhydride was synthesized from the triketone. This conversion is part of the putative biosynthetic pathway and was achieved experimentally for the first time.

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Convergent synthesis of hexameric naphthylene macrocycles with dicarboxylic imide appendages

Cited by 13 publications

References 17 publications

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

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

Conjugated polymers based on 1,8‐naphthalene monoimide with high electron mobility

Total Syntheses of FR-901235, Auxarthrones A–D, and Lamellicolic Anhydride

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