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Designing highly luminescent aryloxy-benzothiadiazole derivatives with aggregation-induced enhanced emission
Dyes and Pigments ( IF 4.5 ) Pub Date : 2020-03-19 , DOI: 10.1016/j.dyepig.2020.108377
Alessandra Pazini , Luis Maqueira , Fabiano da Silveira Santos , Arthur Rodrigues Jardim Barreto , Rafael dos Santos Carvalho , Felipe Miranda Valente , Davi Back , Ricardo Queiroz Aucélio , Marco Cremona , Fabiano Severo Rodembusch , Jones Limberger

A series of luminescent aryloxy-benzothiadiazole derivatives with architectures ArO-BTD-Ar’ and ArO-BTD-NAr’ were synthetized. The aim was to achieve a molecular design based on restriction of intramolecular rotation of the ArO- group associated to the presence of bulky aryl or N-aryl groups, which can avoid detrimental π-π stacking and favor radiative decays in the aggregated/solid state. In solution, these compounds showed fluorescence emission located in the blue to red regions with relative high fluorescence quantum yields (ϕFL = 0.27–0.74). for all ArO-BTD-Ar’ derivatives, emission enhancement was observed upon aggregation. The essential role of the ArO- group in the AIEEgenic ability was confirmed by comparing with Ar’-BTD-Ar’ analogs. Some solid ArO-BTD-Ar’ compounds displayed higher ϕFL than when in solution. Their aggregation-induced enhanced emission (AIEE) were corroborated by studies in water/acetone systems (I/I0 emission rations up to 7.7). Monocrystal X-ray analysis of selected compounds confirmed the twisted nature and absence of detrimental π-π stacking. The more emissive compound (ϕFL = 0.83) was applied as emitting material in a green OLED structure, presenting turn-on voltage around 3.5 V and luminance up to 1200 cd m−2, with a maximum current efficiency of 5.6 × 10−1 cd A−1 at 6.5 V.



中文翻译:

设计具有聚集诱导增强发射的高发光芳氧基-苯并噻二唑衍生物

合成了具有结构ArO-BTD-Ar'和ArO-BTD-NAr'的一系列发光芳氧基-苯并噻二唑衍生物。目的是基于对与庞大的芳基或N-芳基的存在相关的ArO-基团的分子内旋转的限制来实现分子设计,其可以避免有害的π-π堆积并有利于聚集/固态的辐射衰变。在溶液中,这些化合物的荧光发射位于蓝色至红色区域,具有较高的荧光量子产率(quantum FL = 0.27–0.74)。对于所有ArO-BTD-Ar'衍生物,聚集后均观察到发射增强。通过与Ar'-BTD-Ar'类似物进行比较,证实了ArO-基团在AIEE产生能力中的重要作用。一些固态的ArO-BTD-Ar'化合物比溶液中的FL更高。在水/丙酮系统(I / I 0排放比最高为7.7)中的研究证实了它们的聚集诱导的增强排放(AIEE )。所选化合物的单晶X射线分析证实了扭曲性质,并且没有有害的π-π堆积。具有较高发射率的化合物(ϕ FL  = 0.83)被用作绿色OLED结构中的发光材料,其导通电压约为3.5 V,亮度高达1200 cd m -2, 在6.5 V时的最大电流效率为5.6×10 -1  cd A -1

更新日期:2020-03-20
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