Effects of peripheral ring fluorination on the photophysical properties of hexaarylbenzenes
Effects of peripheral ring fluorination on the photophysical properties of hexaarylbenzenes
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外围环氟化对六芳基苯光物理性质的影响
DOI：
10.1016/j.jfluchem.2023.110086
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发表时间：
2023
影响因子：
1.9
通讯作者：
Konno Tsutomu
中科院分区：
文献类型：
--
作者：
Wang Yizhou;Yamada Shigeyuki;Konno Tsutomu
六芳基苯(HABS)表现出有趣的光物理性质，这些性质源于它们的六个扭曲的周边芳环之间的穿透空间电荷转移相互作用。虽然在π共轭结构中引入氟原子可以有效地控制它们的电子密度分布和聚集行为，但外围环氟化对HAB性质的影响仍然没有得到充分的研究。本文介绍了三种不对称的HAB及其对称的区域异构体的合成和光物理性质，即属于0F(周围芳环短分子轴上没有氟原子)、4F(具有CF3端基的芳环短分子轴上的四个氟原子作为取代基)和8F系列(每个周围芳环短分子轴上四个氟原子)的化合物。所有的HABS在溶液和晶体中都显示出蓝色的光致发光。4F系列分子的斯托克斯位移随溶剂极性的增加而增大，具有良好的分子内电荷转移特性，与对称分子相比，非对称分子的光致发光带发生了显著的红移。值得注意的是，4F系列表现出光致变色行为，即当用280 nm紫外光照射它时，在较长波长区域观察到一个额外的吸收带，因此无色溶液获得黄色。因此，HAB支架(4F系列)的部分氟化产生了光致变色行为，同时它的其他光物理性质被保留下来。
Hexaarylbenzenes (HABs) exhibit interesting photophysical properties that originate from the through-space charge-transfer interactions between their six twisted peripheral aromatic rings. Although the introduction of fluorine atoms into π-conjugated structures allows one to effectively control their electron density distribution and aggregation behavior, the effects of peripheral ring fluorination on HAB properties remain underexplored. This paper describes the syntheses and photophysical properties of three unsymmetrical HABs and their symmetrical regioisomers, namely compounds belonging to0F(no fluorine atoms on the short molecular axes of the peripheral aromatic rings),4F(four fluorine atoms as substituents on the short molecular axes of the aromatic rings with CF3end groups), and8Fseries (four fluorine atoms on the short molecular axes of each of the peripheral aromatic rings). All the HABs exhibited blue photoluminescence both in solution and in crystalline form. Molecules in the4Fseries exhibited an increase in their Stokes shift with increasing solvent polarity and featured superior intramolecular charge-transfer properties, which produced a significant redshift of the PL band of the unsymmetrical molecule compared to that of its symmetrical counterpart. It is noteworthy that the4Fseries exhibited photochromic behavior, that is, an additional absorption band in the longer-wavelength region was observed upon irradiating it with 280-nm UV light, and consequently the colorless solution acquired a yellow color . Thus, the partial fluorination of the HAB scaffold (4Fseries) produced photochromic behavior, while its other photophysical properties were preserved.
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