具有树突状电子供体的二苯并二吡啶吩嗪表现出深红色发射和热激活延迟荧光,The Journal of Organic Chemistry

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具有树突状电子供体的二苯并二吡啶吩嗪表现出深红色发射和热激活延迟荧光
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-03-15 , DOI: 10.1021/acs.joc.2c02774
William L Primrose ₁ , Don M Mayder ₁ , Ryoga Hojo ₁ , Zachary M Hudson ₁

Affiliation

深红色热激活延迟荧光 (TADF) 发射器的开发对于有机发光二极管 (OLED) 和生物成像等应用非常重要。红移发射的设计策略包括合成刚性受体核以限制非辐射衰变和使用强电子供体基团。在这项工作中，使用树枝状咔唑制备了三种基于二苯并[ a，c ]联吡啶并[3,2-h:20-30- j ]-吩嗪-12-基 ( BPPZ ) 受体的新型发光供体-受体化合物。基于供体 3,3″,6,6″-tetramethoxy-9′ H -9,3′:6′,9″-tercarbazole ( TMTC ), N ³ , N ³ ,N ⁶ , N ⁶ -tetra- p -tolyl-9 H -carbazole-3,6-diamine ( TTAC ), N ³ , N ³ , N ⁶ , N ⁶ -tetrakis(4-methoxyphenyl)-9 H -carbazole -3,6-二胺 ( TMAC). 在这里，二甲氧基咔唑、二甲苯胺和双（4-甲氧基苯基）胺被引入咔唑的 3,6 位，以增加这些供体的强度并诱导长波长发射。通过实验和理论计算研究了取代基效应。BPPZ-2TMTC、BPPZ-2TTAC和BPPZ-2TMAC的这些材料在甲苯中的发射最大值分别为 562、658 和 680 nm ，突出了TMAC供体的特殊强度，它将发射推入可见光谱的深红色区域以及生物透明窗口 (650–1350 nm)。由于BPPZ-2TMC中的 TADF，在每个发射器中都观察到了长寿命的发射寿命和BPPZ-2TTAC以及BPPZ-2TMAC中的室温磷光。总的来说，这项工作展示了深红色发光的树枝状供体-受体材料，这些材料具有作为生物成像剂的潜力，并在生物透明窗口中发射。

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Dibenzodipyridophenazines with Dendritic Electron Donors Exhibiting Deep-Red Emission and Thermally Activated Delayed Fluorescence

The development of deep-red thermally activated delayed fluorescence (TADF) emitters is important for applications such as organic light-emitting diodes (OLEDs) and biological imaging. Design strategies for red-shifting emission include synthesizing rigid acceptor cores to limit nonradiative decay and employing strong electron-donating groups. In this work, three novel luminescent donor–acceptor compounds based on the dibenzo[a,c]dipyrido[3,2-h:20-30-j]-phenazine-12-yl (BPPZ) acceptor were prepared using dendritic carbazole-based donors 3,3″,6,6″-tetramethoxy-9′H-9,3′:6′,9″-tercarbazole (TMTC), N³,N³,N⁶,N⁶-tetra-p-tolyl-9H-carbazole-3,6-diamine (TTAC), and N³,N³,N⁶,N⁶-tetrakis(4-methoxyphenyl)-9H-carbazole-3,6-diamine (TMAC). Here, dimethoxycarbazole, ditolylamine, and bis(4-methoxyphenyl)amine were introduced at the 3,6-positions of carbazole to increase the strength of these donors and induce long-wavelength emission. Substituent effects were investigated with experiments and theoretical calculations. The emission maxima of these materials in toluene were found to be 562, 658, and 680 nm for BPPZ-2TMTC, BPPZ-2TTAC, and BPPZ-2TMAC, respectively, highlighting the exceptional strength of the TMAC donor, which pushes the emission into the deep-red region of the visible spectrum as well as into the biological transparency window (650–1350 nm). Long-lived emission lifetimes were observed in each emitter due to TADF in BPPZ-2TMC and BPPZ-2TTAC, as well as room-temperature phosphorescence in BPPZ-2TMAC. Overall, this work showcases deep-red emissive dendritic donor–acceptor materials which have potential as bioimaging agents with emission in the biological transparency window.

更新日期：2023-03-15

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