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Synthesis of isoniazid-substituted tetraphenylethylene stereoisomers with dramatic differences on aggregate morphologies, optical and mechanocharomic properties
Journal of Photochemistry and Photobiology A: Chemistry ( IF 4.1 ) Pub Date : 2020-02-08 , DOI: 10.1016/j.jphotochem.2020.112357
Zhixiang Lu , Shuhan Lu , Yi Cheng , Yu Qin , Shaoxiong Yang , Xiaolan Liu , Wenwen Fan , Liyan Zheng , Hongbin Zhang

Stereoisomers play an irreplaceable prominent role in life sciences. In molecular engineering, the isomers have been continuously designed and synthesized, and their interrelationships among structure-property-function have also been explored. However, the difficulties in purification and structural confirmation of tetraphenylethene (TPE) derivatives' stereoisomers hinder their structural diversity and scope of functions. Meanwhile, there were few researches on the macroscopic optical differences about TPE derivatives isomers. Herein, isoniazid-substituted TPE derivatives stereoisomers have been synthesized, as confirmed by single crystal data, mass spectrometry and NMR spectroscopy. The different photophysical properties were caused by the introduction of functional group isoniazid on the periphery of TPE. These isomers possessed dramatic differences in fluorescent properties, and exhibited diverse changes in response to stimuli. They also have distinct aggregated self-assembly morphologies because of different intermolecular hydrogen bonding, and they can be used as efficient fluorescent probes for detecting copper. Based on the coordination-driven sensing system, the morphologies of isomers aggregates changed significantly after interaction with copper, and the stoichiometry between them is 2:1. The theoretical calculation demonstrated that they have obvious intramolecular charge transfer behavior. Our research provided a good strategy for designing different substituted groups that can produce various functions and have more potential applications.



中文翻译:

异烟肼取代的四苯基乙烯立体异构体的合成在聚集体形态,光学和机械致密性方面存在巨大差异

立体异构体在生命科学中扮演着不可替代的重要角色。在分子工程中,异构体是经过不断设计和合成的,并且还探索了它们在结构-性能-功能之间的相互关系。然而,四苯基乙烯(TPE)衍生物的立体异构体的纯化和结构确认困难,阻碍了它们的结构多样性和功能范围。同时,关于TPE衍生物异构体的宏观光学差异的研究很少。在此,已经合成了异烟肼取代的TPE衍生物立体异构体,如通过单晶数据,质谱和NMR光谱所证实的。不同的光物理性质是由在TPE外围引入异烟肼官能团引起的。这些异构体在荧光性质上具有显着差异,并且在对刺激的反应中表现出多种变化。由于分子间氢键的不同,它们还具有独特的聚集的自组装形态,可以用作检测铜的有效荧光探针。基于配位驱动的传感系统,异构体聚集体的形态在与铜相互作用后发生了显着变化,它们之间的化学计量比为2:1。理论计算表明,它们具有明显的分子内电荷转移行为。我们的研究为设计能够产生各种功能并具有更多潜在应用的不同取代基团提供了一个很好的策略。由于分子间氢键的不同,它们还具有独特的聚集的自组装形态,可以用作检测铜的有效荧光探针。基于配位驱动的传感系统,异构体聚集体的形态在与铜相互作用后发生了显着变化,它们之间的化学计量比为2:1。理论计算表明,它们具有明显的分子内电荷转移行为。我们的研究为设计能够产生各种功能并具有更多潜在应用的不同取代基团提供了一个很好的策略。由于分子间氢键的不同,它们还具有独特的聚集的自组装形态,可以用作检测铜的有效荧光探针。在协调驱动的传感系统的基础上,异构体聚集体的形态在与铜相互作用后发生了显着变化,它们之间的化学计量比为2:1。理论计算表明,它们具有明显的分子内电荷转移行为。我们的研究为设计能够产生各种功能并具有更多潜在应用的不同取代基团提供了一个很好的策略。基于配位驱动的传感系统,异构体聚集体的形态在与铜相互作用后发生了显着变化,它们之间的化学计量比为2:1。理论计算表明,它们具有明显的分子内电荷转移行为。我们的研究为设计能够产生各种功能并具有更多潜在应用的不同取代基团提供了一个很好的策略。基于配位驱动的传感系统,异构体聚集体的形态在与铜相互作用后发生了显着变化,它们之间的化学计量比为2:1。理论计算表明,它们具有明显的分子内电荷转移行为。我们的研究为设计能够产生各种功能并具有更多潜在应用的不同取代基团提供了一个很好的策略。

更新日期:2020-02-08
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