N-(hydroxypentanyl)-cis-5-norbornene-exo-2,3-dicarboximide | 1394169-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(hydroxypentanyl)-cis-5-norbornene-exo-2,3-dicarboximide
• 英文别名: (1R,2R,6S,7S)-4-(5-hydroxypentyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• CAS: 1394169-17-5
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: JQPAOXLVGUVREB-IWDIQUIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-己炔酸 、 N-(hydroxypentanyl)-cis-5-norbornene-exo-2,3-dicarboximide 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以84%的产率得到N-(pentynoylhexanyl)-cis-5-norbornene-exo-2,3-dicarboximide
  参考文献：
  名称：

  Surface Properties of Bottlebrush Polymer Thin Films

  摘要：

  Bottlebrush polymer thin films may be attractive for the preparation of antifouling and/or stimuli-responsive surface coatings due to the high grafting density and conformational flexibility of polymeric side chains, but bottlebrush polymer thin films have not been previously reported and their surface properties are unknown. Herein, we report a study of the surface properties of mixed bottlebrush polymer (MBBPs) films. MBBPs with hydrophobic polystyrene (PS) and hydrophilic poly(ethylene glycol) (PEG) side chains are synthesized using a "grafting-through" ring-opening metathesis polymerization (ROMP) approach. Stimuli-responsive MBBPs films are prepared by spin-casting a solution of MBBPs onto a solid surface, and the resulting film morphology and surface properties are characterized using atomic force microscopy (AFM), grazing-incidence small-angle X-ray scattering (GISAXS), water contact angle measurements, and X-ray photoelectron spectroscopy (XPS). The water contact angles of MBBPs films decrease or increase upon exposure of the MBBPs films to selective solvents methanol or cyclohexane, respectively. This contact angle change is dependent on the length of the PEG side chain; longer PEG side chains result in greater contact angle changes with solvent exposure. Consistent with water contact angle measurements, XPS indicates enrichment of PEG or PS chains at the film surface after exposure of the MBBPs film to methanol or cyclohexane solvent vapors, respectively. Finally, it is demonstrated that bottlebrush polymer films can be stabilized by the addition of a radical cross-linker and irradiation with UV light. This work demonstrates that bottlebrush polymers enable the preparation of stimuli-responsive, "brush-like" polymeric coatings using simple solution processing methods.

  DOI：

  10.1021/ma301046n
• 作为产物：
  描述：

  5-氨基-1-戊醇 、 (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以96%的产率得到N-(hydroxypentanyl)-cis-5-norbornene-exo-2,3-dicarboximide
  参考文献：
  名称：

  Surface Properties of Bottlebrush Polymer Thin Films

  摘要：

  Bottlebrush polymer thin films may be attractive for the preparation of antifouling and/or stimuli-responsive surface coatings due to the high grafting density and conformational flexibility of polymeric side chains, but bottlebrush polymer thin films have not been previously reported and their surface properties are unknown. Herein, we report a study of the surface properties of mixed bottlebrush polymer (MBBPs) films. MBBPs with hydrophobic polystyrene (PS) and hydrophilic poly(ethylene glycol) (PEG) side chains are synthesized using a "grafting-through" ring-opening metathesis polymerization (ROMP) approach. Stimuli-responsive MBBPs films are prepared by spin-casting a solution of MBBPs onto a solid surface, and the resulting film morphology and surface properties are characterized using atomic force microscopy (AFM), grazing-incidence small-angle X-ray scattering (GISAXS), water contact angle measurements, and X-ray photoelectron spectroscopy (XPS). The water contact angles of MBBPs films decrease or increase upon exposure of the MBBPs films to selective solvents methanol or cyclohexane, respectively. This contact angle change is dependent on the length of the PEG side chain; longer PEG side chains result in greater contact angle changes with solvent exposure. Consistent with water contact angle measurements, XPS indicates enrichment of PEG or PS chains at the film surface after exposure of the MBBPs film to methanol or cyclohexane solvent vapors, respectively. Finally, it is demonstrated that bottlebrush polymer films can be stabilized by the addition of a radical cross-linker and irradiation with UV light. This work demonstrates that bottlebrush polymers enable the preparation of stimuli-responsive, "brush-like" polymeric coatings using simple solution processing methods.

  DOI：

  10.1021/ma301046n

文献信息

• Functional bottlebrush polymers
  申请人：Florida State University Research Foundation, Inc.

  公开号：US10894854B2

  公开（公告）日：2021-01-19

  An example of a bottlebrush polymer has a polymer backbone and a plurality of individual brush moieties bonded to the polymer backbone. The individual brush moieties respectively including a ketone, a hydrophilic segment, and a surface adhesive terminal group. The brush moieties can be functionalized and/or cross-linked.

  底刷聚合物的一个例子是聚合物骨架和多个与聚合物骨架粘合的单个刷分子。单个刷分子分别包括一个酮、一个亲水段和一个表面粘合末端基团。这些刷分子可以被官能化和/或交联。
• Functional Bottlebrush Polymers
  申请人：Florida State University Research Foundation, Inc.

  公开号：US20180312634A1

  公开（公告）日：2018-11-01

  An example of a bottlebrush polymer has a polymer backbone and a plurality of individual brush moieties bonded to the polymer backbone. The individual brush moieties respectively including a ketone, a hydrophilic segment, and a surface adhesive terminal group. The brush moieties can be functionalized and/or cross-linked.