2-Phenylbenzothiophene-based liquid crystalline semiconductors

2-Phenylbenzothiophene-based liquid crystalline semiconductors
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2-苯基苯并噻吩类液晶半导体

DOI:
10.1016/j.dyepig.2019.107964
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发表时间:
2020-02
期刊:
影响因子:
4.5
通讯作者:
Donnio Bertr
Donnio Bertr
中科院分区:
材料科学2区
文献类型:
--
作者:
Zhong Yu-Jie;Zhao Ke-Qing;Wang Bi-Qin;Hu Ping;Monobe Hirosato;Heinrich Benoit;Donnio Bertr

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本文报道了由具有生物活性的结构单元分子6-甲氧基-2-(4-甲氧基苯基)苯并[B]噻吩(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene)构建的新型液晶半导体的设计和合成,这些液晶半导体具有高效的发光和中等的电荷迁移率。第一系列的介晶2-苯基苯并噻吩衍生物(nPBT)简单,快速地获得良好的产率通过连续的脱甲基/烷基化反应的可用的甲氧基前体。进一步逐步氧化,而且导致在两个新的相应的亚砜(nPBTO)和砜(nPBTO 2)衍生物,分别,也是介晶的。用DSC、POM和SAXS等手段对化合物的液晶行为进行了全面的表征:所有化合物均表现出与其棒状结构一致的类近晶行为。更具体地,介晶PBT显示出SmA相,此外,在较低温度下具有更高有序的近晶相。对于氧化的介晶,它们只显示SmA相,并且对于链长较长(n≥ 8)的PBTO,它们在特别大的温度范围内显示SmA相。还研究了溶液和薄膜中的光物理性质,发现分子在UV/维斯域中显示出强吸收,并在400-650 nm范围内(黄色绿色光)以高量子产率(高达62%)显示出强烈的发光。吸收和发光也被发现受到苯并噻吩部分的氧化。最后,用光电流飞行时间技术研究了三种PBT化合物在不同中间相的半导体行为。空穴迁移率。在较低温度的有序中间相中,所有这些化合物都测得了4 × 10− 3cm 2 V − 1 s − 1,但最短同系物(n= 6)的性能(温度范围和迁移率值)最好。由于这些材料具有高度合理的介晶、发光和半导体功能特征,以及便宜且易于合成和加工,这些材料变得非常有吸引力,并且可以被并入各种电子器件(OFET和OLED)中。
We report herein the design and synthesis of some novel liquid crystalline semiconductors constructed from a biologically and pharmacologically active building block molecule, namely 6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene, presenting efficient luminescence and medium charge mobility rate. A first series of mesogenic 2-phenylbenzothiophene derivatives (nPBT) was simply and rapidly obtained in good yields by successive demethylation/alkylation reactions of the available methoxy precursor. The further stepwise oxidations moreover resulted in two new sets of the corresponding sulfoxide (nPBTO) and sulfone (nPBTO2) derivatives, respectively, that were also mesomorphic. The liquid crystalline behaviour was comprehensively characterized by DSC, POM and SAXS: all compounds exhibit smectic-like behaviour in agreement with their calamitic shape. More specifically, mesogensnPBT showed a SmA phase, with in addition, a higher ordered smectic phase at lower temperature. As for the oxidized mesogens, they displayed a SmA phase only, and over particularly large temperature ranges for thenPBTO with longer chain lengths (n≥ 8). The photo-physical properties have also been studied both in solution and thin films, and the molecules were found to display strong absorption in the UV/vis domain and intense luminescence in the range of 400–650 nm (yellowish green light) in high quantum yields (up to 62%). Both absorption and luminescence were also found to be affected by the oxidation of the benzothiophene moiety. Finally, the semi-conducting behaviour of three PBT compounds in the various mesophases was investigated by photocurrent TOF technique. Hole mobility rates of ca. 4 × 10−3cm2V−1s−1were measured in the lower temperature ordered mesophase for all of them, with the best performances (temperature range and mobility values) however obtained for the shortest homolog (n= 6). With such highly reasonable mesomorphic, light-emitting and semiconducting functional features, as well as being cheap and easy to synthesize and to process, these materials become very attractive and may be incorporated into various kinds of electronic devices (OFET and OLED).
DOI: 10.1038/srep00754
发表时间: 2012
期刊: SCIENTIFIC REPORTS
影响因子: 4.6
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影响因子: 8.6
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发表时间: 2006-08-01
影响因子: 3.1
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