Synthesis, structural and spectral properties of diarylamino-functionalized pyrene derivatives via Buchwald–Hartwig amination reaction

Hu, Jian‐Yong; Feng, Xing; Seto, Nobuyuki; Do, Jung‐Hee; Zeng, Xi; Zhu, Tao; Yamato, Takehiko

doi:10.1016/j.molstruc.2012.09.028

Cited by 22 publications

(12 citation statements)

References 34 publications

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“…It is also interesting to compare the absorption parameters of 3d and 3e with N,N-diphenylpyren-1-amine. 29 The l max (379 nm) 29 of N,N-diphenylpyren-1-amine is similar to 3d and 3e which suggests that the introduction of benzimidazole unit on the periphery of triarylamine did not alter the l max . So, benzimidazole decoration on blue-emitting materials can be performed to impart electron-transport capability while retaining the absorption characteristics.…”

Section: Photophysical Propertiesmentioning

confidence: 81%

Deep-blue emitting pyrene–benzimidazole conjugates for solution processed organic light-emitting diodes

et al. 2015

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Section: Photophysical Propertiesmentioning

confidence: 81%

Deep-blue emitting pyrene–benzimidazole conjugates for solution processed organic light-emitting diodes

et al. 2015

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“…Fluorescent intermediate compound 2 was synthesized according to Scheme A. In the first step, selective mono‐bromination of pyrene with one equivalent of N‐ bromosuccinimide in the presence of anhydrous dimethylformamide gave compound 1 in 52 % yield, which was subsequently lithiated using n‐BuLi, followed by treating it with1,6‐dibromo hexane to isolatecompound 2 in 21 % yield . Such low yield can be explained by the formation of dimeric form of this compound: (1,6‐di(pyren‐1‐yl)hexane).…”

Section: Methodsmentioning

confidence: 99%

Antibacterial Nanoparticles Based on Fluorescent 3‐Substituted Uridine Analogue

et al. 2017

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With a sudden and rapid increase in the spread of antimicrobial resistance, there is an urgent need for the development of novel antimicrobial therapies. Nanoparticles with antimicrobial activity provide advantages such as improved solubility, permeability, stability and selectivity. In this study, a uridine‐scaffold was connected to a pyrene fluorescent unit to obtain novel compound UPy via an economical and straightforward route. Further, fluorescent organic nanoparticles (FONs) were prepared via self assembly of UPy and were found to have antibacterial activity towards Gram positive bacteria. The fluorescent nature of the FONs allowed us to identify a binding partner and propose mechanism of action in vivo. We believe that UPy can be an excellent starting point for the development of novel, potent and selective antimicrobial nanotherapeutics.

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“…In particular, 1,3,6,8‐tetrasubstituted pyrenes as host materials have been widely applied in OLEDs and OFETs devices as well as in solar cells . For instance, the Buchwald–Hartwig amination reaction of 1,3,6,8‐tetrabromopyrenes 31 – 35 with N , N ‐di(4‐methylphenyl)amine afforded the 1‐, 1,6‐, and 1,8‐, and 1,3,6,8‐ N , N ‐di(4‐methylphenyl)amino‐substituted compounds 36 a – e in good yields (Scheme ) . All compounds of type 36 exhibit bright fluorescent emission from sky‐blue to green in solution ( λ max =464–500 nm in CH 2 Cl 2 ) and exhibit high emission efficiency ( Φ f = 0.84–0.96 in dichloromethane).…”

Section: Bromination Of Pyrenementioning

confidence: 99%

Functionalization of Pyrene To Prepare Luminescent Materials—Typical Examples of Synthetic Methodology

Feng

Redshaw

et al. 2016

Chemistry A European J

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215

144

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Pyrene-based π-conjugated materials are considered to be an ideal organic electro-luminescence material for application in semiconductor devices, such as organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs) and organic photovoltaics (OPVs), and so forth. However, the great drawback of employing pyrene as an organic luminescence material is the formation of excimer emission, which quenches the efficiency at high concentration or in the solid-state. Thus, in order to obtain highly efficient optical devices, scientists have devoted much effort to tuning the structure of pyrene derivatives in order to realize exploitable properties by employing two strategies, 1) introducing a variety of moieties at the pyrene core, and 2) exploring effective and convenient synthetic strategies to functionalize the pyrene core. Over the past decades, our group has mainly focused on synthetic methodologies for functionalization of the pyrene core; we have found that formylation/acetylation or bromination of pyrene can selectly lead to functionalization at K-region by Lewis acid catalysis. Herein, this Minireview highlights the direct synthetic approaches (such as formylation, bromination, oxidation, and de-tert-butylation reactions, etc.) to functionalize the pyrene in order to advance research on luminescent materials for organic electronic applications. Further, this article demonstrates that the future direction of pyrene chemistry is asymmetric functionalization of pyrene for organic semiconductor applications and highlights some of the classical asymmetric pyrenes, as well as the latest breakthroughs. In addition, the photophysical properties of pyrene-based molecules are briefly reviewed. To give a current overview of the development of pyrene chemistry, the review selectively covers some of the latest reports and concepts from the period covering late 2011 to the present day.

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Synthesis, structural and spectral properties of diarylamino-functionalized pyrene derivatives via Buchwald–Hartwig amination reaction

Cited by 22 publications

References 34 publications

Deep-blue emitting pyrene–benzimidazole conjugates for solution processed organic light-emitting diodes

Deep-blue emitting pyrene–benzimidazole conjugates for solution processed organic light-emitting diodes

Antibacterial Nanoparticles Based on Fluorescent 3‐Substituted Uridine Analogue

Functionalization of Pyrene To Prepare Luminescent Materials—Typical Examples of Synthetic Methodology

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