Synthesis and Photophysical Properties of Pyrene-Based Multiply Conjugated Shaped Light-Emitting Architectures: Toward Efficient Organic-Light-Emitting Diodes

Hu, Jian‐Yong; Yamato, Takehiko

doi:10.5772/19271

Cited by 9 publications

(21 citation statements)

References 82 publications

(84 reference statements)

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“…π‐Extended arenes have attracted the attention of materials scientists in the last few decades owing to their beneficial characteristics such as good charge mobilities and often outstanding optical properties . These physicochemical properties have found applications in sensors, field‐effect transistors, and light‐emitting diodes . In particular, the efficient electronic delocalization within the π‐systems is responsible for the optoelectronic properties of arenes.…”

Section: Introductionmentioning

confidence: 99%

Phosphorus Post‐Functionalization of Diphosphahexaarenes

Hindenberg

Röminger

Romero‐Nieto

2019

Chemistry A European J

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Diphosphahexaarenes are highly stable π‐extended frameworks containing two six‐membered phosphorus heterocycles that have emerged recently. Herein, we present a detailed investigation on the post‐functionalization reactions of their phosphorus centers with special emphasis on the selectivity of the processes and the impact of the phosphorus functionalizations into the physicochemical properties. These studies reveal that indeed the phosphorus atoms of the diphosphahexaarenes are readily available to be functionalized with quaternizing and oxidizing agents as well as borane groups without compromising the stability of the system. In addition, the optoelectronic properties of the diphosphahexaarenes are impacted by the phosphorus post‐modifications.

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Section: Introductionmentioning

confidence: 99%

Phosphorus Post‐Functionalization of Diphosphahexaarenes

Hindenberg

Röminger

Romero‐Nieto

2019

Chemistry A European J

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“…However, the most important clue is the great sensitivity of fluorophore to microenvironment changes, providing detailed information about the properties of the investigated system (like micropolarity, microviscosity). By tailoring the fluorophore structure (derivatization, attaching a lateral chain, immobilizing on a polymer chain) one obtains suitable chemosensors for biological, environmental or other purposes [6][7][8][9][10][11]. Depending on application, the fluorophore can be probe or label.…”

Section: Introductionmentioning

confidence: 99%

Comparing the spectral properties of pyrene as free molecule, label and derivative in some colloidal systems

Băran¹,

Stîngă²,

Anghel³

et al. 2014

Sensors and Actuators B: Chemical

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“…3−6 Among these luminophores, pyrene provides great potential for fabrication of OLEDs blue emitters owing to its high thermal and photo stabilities, favorable charge carrier properties, and spectral characteristics. 5,7 Consequently, a number of pyrene derivatives have already been reported as blue/green OLED emitters 7−12 as well as charge injectors/transporters in OLEDs. 7,13−18 More importantly, pyrene derivatives can be designed as multifunctional p-type, n-type, or bipolar emitters, ensuring an efficient and balanced flux of charges to the emissive layer even with relatively simple device architectures.…”

Section: Introductionmentioning

confidence: 99%

“…5,7 Consequently, a number of pyrene derivatives have already been reported as blue/green OLED emitters 7−12 as well as charge injectors/transporters in OLEDs. 7,13−18 More importantly, pyrene derivatives can be designed as multifunctional p-type, n-type, or bipolar emitters, ensuring an efficient and balanced flux of charges to the emissive layer even with relatively simple device architectures. 3,7…”

Section: Introductionmentioning

confidence: 99%

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Pyrenylpyridines: Sky-Blue Emitters for Organic Light-Emitting Diodes

et al. 2019

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A novel sky-blue-emitting tripyrenylpyridine derivative, 2,4,6-tri(1-pyrenyl)pyridine (2,4,6-TPP), has been synthesized using a Suzuki coupling reaction and compared with three previously reported isomeric dipyrenylpyridine (DPP) analogues (2,4-di(1-pyrenyl)pyridine (2,4-DPP), 2,6-di(1-pyrenyl)pyridine (2,6-DPP), and 3,5-di(1-pyrenyl)pyridine (3,5-DPP)). As revealed by single-crystal X-ray analysis and computational simulations, all compounds possess highly twisted conformations in the solid state with interpyrene torsional angles of 42.3°–57.2°. These solid-state conformations and packing variations of pyrenylpyridines could be correlated to observed variations in physical characteristics such as photo/thermal stability and spectral properties, but showed only marginal influence on electrochemical properties. The novel derivative, 2,4,6-TPP, exhibited the lowest degree of crystallinity as revealed by powder X-ray diffraction analysis and formed amorphous thin films as verified using grazing-incidence wide-angle X-ray scattering. This compound also showed high thermal/photo stability relative to its disubstituted analogues (DPPs). Thus, a nondoped organic light-emitting diode (OLED) prototype was fabricated using 2,4,6-TPP as the emissive layer, which displayed a sky-blue electroluminescence with Commission Internationale de L’Eclairage (CIE) coordinates of (0.18, 0.34). This OLED prototype achieved a maximum external quantum efficiency of 6.0 ± 1.2% at 5 V. The relatively high efficiency for this simple-architecture device reflects a good balance of electron and hole transporting ability of 2,4,6-TPP along with efficient exciton formation in this material and indicates its promise as an emitting material for design of blue OLED devices.

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Synthesis and Photophysical Properties of Pyrene-Based Multiply Conjugated Shaped Light-Emitting Architectures: Toward Efficient Organic-Light-Emitting Diodes

Cited by 9 publications

References 82 publications

Phosphorus Post‐Functionalization of Diphosphahexaarenes

Phosphorus Post‐Functionalization of Diphosphahexaarenes

Comparing the spectral properties of pyrene as free molecule, label and derivative in some colloidal systems

Pyrenylpyridines: Sky-Blue Emitters for Organic Light-Emitting Diodes

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