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Semiconducting Self-Assembled Nanofibers Prepared from Photostable Octafluorinated Bisanthene Derivatives

机译:由光稳定的八磺丙烯衍生物制备的半导体自组装纳米纤维

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摘要

Bisanthene is an important class of small two-dimensional polycyclic aromatic hydrocarbons with a zigzagedged graphene nanoribbon character. Therefore, the functionalization and deep understanding of the structure–property relationship of bisanthene would provide an effective design for small organic molecular devices. In this study, octa- and tetrafluorinated bisanthene derivatives were synthesized for investigating the effect of electronegative fluorine substitution on the structure and physical property of bisanthene. Firstly, the octafluorinated bisanthene derivative has a twisted structure due to the steric repulsion of fluorine atoms at the bay region. Secondly, the absorption and fluorescence peak maxima are blueshifted with an increase in the degree of fluorine substitution. Notably, a triisopropylsilylethynyl- substituted octafluorinated derivative (F8) exhibited strong fluorescence at 657 nm with high fluorescence quantum yield (84 %). Additionally, cyclic voltammograms indicate the positive effect of fluorine substitution on the high highest occupied molecular orbital energy level of the molecules; thus, F8 molecule exhibited a remarkably increased photostability. Finally, the self-assembled behavior of fluorinated compounds was investigated by scanning electron microscopy and X-ray diffraction analysis. Specifically, F8 selfassembled to form bundles of long semicrystalline nanofibers exhibiting hole-transporting properties (3.4× 10~(-3) cm~2V~(-1) s~(-1)).
机译:Bisanthene是一种重要的二维多环芳烃烃,具有Z字形的石墨烯纳米孔特征。因此,对小苯内酯的结构性质关系的官能化和深入理解将为小型有机分子装置提供有效的设计。在该研究中,合成了Octa和四氟化的双苯胺衍生物,用于研究电信氟取代对白鞣结构和物理性质的影响。首先,由于湾地区的氟原子的空间排斥,八氟吡啶衍生物具有扭曲的结构。其次,吸收和荧光峰值最大化以氟取代程度的增加。值得注意的是,三异丙基甲酰基炔基取代的八异丙基甲酰基取代的八氟化衍生物(F8)在657nm处具有高荧光量子产率(84%)的强荧光。另外,循环伏安图表明氟取代对分子的高最高占用分子轨道能量水平的积极作用;因此,F8分子表现出显着提高的光稳定性。最后,通过扫描电子显微镜和X射线衍射分析研究了氟化化合物的自组装行为。具体而言,F8自相色谱以形成具有孔输送性能的长半晶纳米纤维的束(3.4×10〜(-3)cm〜2V〜(-1)S〜(-1))。

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