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首页> 外文期刊>RSC Advances >The influence of different N-substituted groups on the mechanochromic properties of 1,4-dihydropyridine derivatives with simple structures
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The influence of different N-substituted groups on the mechanochromic properties of 1,4-dihydropyridine derivatives with simple structures

机译：不同N-取代基对1,4-二氢吡啶衍生物用简单结构的影响

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摘要

A twisted molecular conformation is known to be beneficial to the formation of mechanochromic (MC) phenomenon for organic fluorescent molecules, but it is sometimes not a decisive factor. Up to now, the clear design guidance for MC-active materials based on these twisted molecules is still lacking. Herein, four twisted 1,4-dihydropyridine derivatives (3a-3d) with a simple structure were synthesized to investigate the effect of N-substituted groups on their potential MC activities. Compound 3d containing 2-phenylethyl group presented reversible high-contrast MC properties, while 3a with an ethyl group and 3c with a 1-phenylethyl group were MC-inactive. Moreover, 3b with a benzyl group had two different crystalline forms, interestingly, the blue-emitting 3b-B was MC-active, whereas the green-emitting 3b-G was MC-inactive. The results indicated that N-substituted groups played a decisive role in determining whether or not these compounds had MC activities. Through the careful analyses of their X-ray diffraction and differential scanning calorimetry experiments, it was found that the phase transformation between different crystalline states was responsible for the reversible MC properties of 3b-B and 3d. Furthermore, the red shift of their fluorescence spectra was ascribed to the planarization of molecular conformation and the resultant enhancement of the degree of pi-electron conjugation. This work provides a feasible design direction for the development of efficient MC materials based on twisted fluorescent molecules.
机译：已知扭曲的分子构象是有益于为有机荧光分子的机械光学（MC）现象的形成，但有时不是决定性因素。到目前为止，仍然缺乏基于这些扭曲分子的MC-活性材料的明确设计指导。这里，合成了具有简单结构的四种捻合1,4-二氢吡啶衍生物（3A-3D），以研究N-取代基团对其潜在MC活性的影响。含有2-苯基乙基的化合物3D呈现可逆的高对比度MC特性，而具有乙基和3℃的3A与1-苯基乙基的3A是MC-无活性。此外，具有苄基的3B具有两种不同的结晶形式，有趣的是，蓝光3B-B是MC-活性的，而绿色发射3B-G是MC-无活性的。结果表明，N-取代基团在确定这些化合物是否具有MC活性时起着决定性作用。通过仔细分析它们的X射线衍射和差分扫描量热法实验，发现不同结晶状态之间的相变负责3B-B和3D的可逆MC特性。此外，将荧光光谱的红色移位归因于分子构象的平坦化和所得增强PI-电子缀合程度。这项工作为基于扭曲的荧光分子的高效MC材料提供了可行的设计方向。

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  • 来源
    《RSC Advances》 |2017年第81期|共8页
  • 作者

    Zhou Yibin; Qian Lebin; Liu Miaochang; Wu Ge; Gao Wenxia; Ding Jinchang; Huang Xiaobo; Wu Huayue;

  • 作者单位

    Wenzhou Univ Coll Chem &

    Mat Engn Wenzhou 325035 Peoples R China;

    Wenzhou Univ Coll Chem &

    Mat Engn Wenzhou 325035 Peoples R China;

    Wenzhou Univ Coll Chem &

    Mat Engn Wenzhou 325035 Peoples R China;

    Wenzhou Med Univ Sch Pharm Wenzhou 325035 Peoples R China;

    Wenzhou Univ Coll Chem &

    Mat Engn Wenzhou 325035 Peoples R China;

    Wenzhou Univ Coll Chem &

    Mat Engn Wenzhou 325035 Peoples R China;

    Wenzhou Univ Coll Chem &

    Mat Engn Wenzhou 325035 Peoples R China;

    Wenzhou Univ Coll Chem &

    Mat Engn Wenzhou 325035 Peoples R China;

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  • 正文语种 eng
  • 中图分类 化学;
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