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首页> 外文期刊>Chemistry: A European journal >Porphyrin, phthalocyanine and porphyrazine derivatives with multifluorenyl substituents as efficient deep-red emitters
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Porphyrin, phthalocyanine and porphyrazine derivatives with multifluorenyl substituents as efficient deep-red emitters

机译：具有多芴基取代基的卟啉，酞菁和卟啉衍生物可作为有效的深红色发射体

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摘要

The synthesis and photophysical properties are described for a series of porphyrin, phthalocyanine and pyrazinoporphyrazine derivatives which bear four or eight peripheral fluorenyl substituents as antennae. Representative examples are 5,10,15,20-tetra (9,9-dihexyl-9H-fluoren-2-yl)porphyrin (2), 5,10,15,20-tetrakis[4-(9,9-dihexyl-9H-fluoren-2-yl)phenyl]porphy- rin (3), 2,3,9,10,16,17,23,24-octakis(9,9dihexyl-9H-fluoren-2-yl)-29H,31H- phthalocyanine (8) and 2,3,9,10,16,17,23,24-octakis[4-(9,9-dihexyl-9H-fluo- ren-2-yl)phenyl]-29H,31H-tetra-apyrazinoporphyrazine (9). Palladium-mediated Suzuki-Miyaura cross-coupling reactions have been key steps for attaching the substituents. The compounds are deep-red emitters: lambda(max)(em) = 659 (3), 737 (8) and 684 nm (9). Their absorption and emission spectra, their fluorescence lifetimes and quantum yields are correlated with the structures of the macrocycles and the substituents. The solution fluorescence quantum yields of porphyrin derivatives substituted with fluorene (24) and terphenyl substituents (7) (Phi(f)= 0.21-0.23) are approximately twice that of tetraphenylporphyrin. For phthalocyanine derivative 8, Of was very high (0.88). Specific excitation of the fluorene units of 8 produced emission from both of them (lambda(max)=480nm) and also from the phthalocyanine core (lambda(max) = 750 nm), indicating a competitive rate of energy transfer and radiative decay of the fluorenes. Organic light-emitting devices (OLEDs) were made by spin-coating techniques by using a polyspirobifluorene (PSBF) copolymer as the host blended with 3 (5 wt.%) in the configuration ITO/PEDOT:PSS/ PSBF copolymer:3/Ca/Al. Deep-red emission (lambda(max)=663nm; CIE coordinates x=0.70, y=0.27) was observed with an external quantum efficiency of 2.5% (photons/electron) (at 7.5 mA cm(-2)), a low turn-on voltage and high emission intensity (luminance) of 5500 cd m(-1) (at 250 mA/ m(2)).
机译：描述了一系列带有四个或八个外围芴基取代基的卟啉，酞菁和吡嗪并卟啉衍生物的合成和光物理性质。代表性的例子是5,10,15,20-四（9,9-二己基-9H-芴-2-基）卟啉（2），5,10,15,20-四[4（9,9-二己基-9H-芴-2-基）苯基]卟啉（3），2,3,9,10,16,17,23,24-辛基（9,9dihexyl-9H-芴-2-基）-29H ，31H-酞菁（8）和2,3,9,10,16,17,23,24-辛基[4-（9,9-二己基-9H-氟-人-2-基）苯基] -29H， 31H-四-吡嗪并卟啉（9）。钯介导的Suzuki-Miyaura交叉偶联反应是连接取代基的关键步骤。这些化合物是深红色发射体：lambda（max）（em）= 659（3），737（8）和684 nm（9）。它们的吸收和发射光谱，其荧光寿命和量子产率与大环和取代基的结构相关。被芴（24）和三联苯取代基（7）（Phi（f）= 0.21-0.23）取代的卟啉衍生物的溶液荧光量子产率约为四苯基卟啉的两倍。对于酞菁衍生物8，Of非常高（0.88）。 8个芴单元的特定激发从它们两者（lambda（max）= 480nm）以及从酞菁核（lambda（max）= 750 nm）产生发射，表明其竞争性的能量转移速率和辐射衰减芴。通过使用聚螺双芴（PSBF）共聚物作为主体与3（5 wt。％）配成ITO / PEDOT：PSS / PSBF共聚物：3 / Ca的主体通过旋涂技术制造有机发光器件（OLED） /铝观察到深红色发射（λ（max）= 663nm; CIE坐标x = 0.70，y = 0.27），外部量子效率为2.5％（光子/电子）（在7.5 mA cm（-2）时），低开启电压和5500 cd m（-1）的高发射强度（亮度）（在250 mA / m（2）时）。

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