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Chiral Nanoparticle-lnduced Enantioselective Amplification of Molecular Optical Activity

机译：手性纳米粒子诱导的分子光学活性的对映选择性扩增

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摘要

Enantiodifferentiation is of fundamental importance in chiral chemistry and substantially requires high optical activity (OA) of enantiomers; but the enantiomeric OA is typically weak due to subwavelength molecular dimension, leading to a lack of sensitive enantiodifferentiation. A new approach is devised to evidently amplify the enantiomeric OA by anchoring axially chiral molecules containing the binaphthyl chromophore on silver chiral nanoparticles (AgCNPs) with a sub-5 nm helical pitch (P). Compared to the OA of dissolved enantiomers, that of (R)- and (S)- enantiomers can be enantioselectively amplified on right-handed and left-handed AgCNPs, respectively, in as high as one order of magnitude. The enantioselective amplification is probably ascribed to the enantiospecific adsorption-induced change in the dihedral angle of the binaphthyl chromophore, resulting from chirality transfer from chiral footprints of the AgCNPs to the binaphthyl chromophore through the Ag-S bicontacts. The enantioselective amplification tends not to occur as long as P 5 nm or on achiral Ag nanoparticles, due to a lack of the chirality transfer. This work imposes the significant application of enantiodifferentiation, which is on practical demand for producing single-enantiomer pharmaceutics and pesticides with no fatal adverse effect, on the emerging chiral metamaterials composed of metallic CNPs.
机译：对映区别在手性化学中至关重要，并且实质上需要对映异构体具有高旋光性（OA）。但是由于亚波长分子尺寸的原因，对映体OA通常较弱，导致缺乏灵敏的对映异构。设计了一种新的方法，通过将包含联萘生色团的轴向手性分子锚定在小于5 nm的螺距（P）的银手性纳米颗粒（AgCNPs）上，明显扩增对映体OA。与溶解的对映异构体的OA相比，（R）-和（S）-对映异构体的OA可以分别在右手和左手AgCNPs上对映选择性地扩增，数量级高达一个数量级。对映选择性扩增可能归因于对映体吸附诱导的联萘生色团二面角的变化，这是由于从手性足迹从AgCNPs的手性足迹通过Ag-S双接触转移到联萘生色团的结果。由于缺乏手性转移，只要P> 5 nm或在非手性Ag纳米颗粒上，对映选择性扩增往往不会发生。这项工作对新兴的由金属CNP组成的手性超颖材料强加了对映异构化的重要应用，对映异构是实际生产单对映异构体药物和农药而无致命不利影响的实际需求。

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  • 来源
    《Advanced Functional Materials》 |2019年第8期|1807307.1-1807307.8|共8页
  • 作者

    Yang Lin; Kwan Chak-Shing; Zhang Lianglin; Li Xinghua; Han Yu; Leung Ken Cham-Fai; Yang Yonggang; Huang Zhifeng;

  • 作者单位

    HKBU, Dept Phys, Kowloon Tong, Kowloon, Hong Kong, Peoples R China;

    HKBU, Dept Chem, Kowloon Tong, Kowloon, Hong Kong, Peoples R China;

    Soochow Univ, Jiangsu Key Lab Adv Funct Polymer Design & Applic, State & Local Joint Engn Lab Novel Funct Polymer, Coll Chem Chem Engn & Mat Sci,Dept Polymer Sci &, Suzhou 215123, Peoples R China;

    King Abdullah Univ Sci & Technol, Phys Sci & Engn Div, Thuwal 239556900, Saudi Arabia;

    King Abdullah Univ Sci & Technol, Phys Sci & Engn Div, Thuwal 239556900, Saudi Arabia;

    HKBU, Dept Chem, Kowloon Tong, Kowloon, Hong Kong, Peoples R China|HKBU, Partner State Key Lab Environm & Biol Anal, Kowloon Tong, Kowloon, Hong Kong, Peoples R China;

    Soochow Univ, Jiangsu Key Lab Adv Funct Polymer Design & Applic, State & Local Joint Engn Lab Novel Funct Polymer, Coll Chem Chem Engn & Mat Sci,Dept Polymer Sci &, Suzhou 215123, Peoples R China;

    HKBU, Dept Phys, Kowloon Tong, Kowloon, Hong Kong, Peoples R China|HKBU, Partner State Key Lab Environm & Biol Anal, Kowloon Tong, Kowloon, Hong Kong, Peoples R China|HKBU, Inst Adv Mat, Kowloon Tong, Kowloon, Hong Kong, Peoples R China|HKBU, Inst Res & Continuing Educ 9F, Ind Complex Shenzhen Virtual Univ Pk, Shenzhen 518057, Guangdong, Peoples R China;

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  • 正文语种 eng
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  • 关键词

    chiral nanoparticles; circular dichroism; enantiomers; glancing angle deposition; optical activity;

    机译：手性纳米粒子圆二色性对映体掠角沉积光学活性;

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