4-(1,3,2-dioxaborinan-2-yl)-benzaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(1,3,2-dioxaborinan-2-yl)-benzaldehyde
• 英文别名: 4-(1,3,2-dioxaborinan-2-yl)benzaldehyde；4-(1,3-dioxaborinan-2-yl)benzaldehyde
• 化学式: C₁₀H₁₁BO₃
• mdl: MFCD04039026
• 分子量: 190.007
• InChiKey: AMQBUMNOSGJNQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1,3,2-dioxaborinan-2-yl)-benzaldehyde 在 zinc diacetate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 41.0h， 生成 5,15-bis(4-dihydroxyboronophenyl)porphyrinatozinc(II)
  参考文献：
  名称：

  利用正同向变构的人工路易斯寡糖结合系统的首次成功分子设计

  摘要：

  我们设计了苯基硼酸基团附加的 Ce(IV) 双（卟啉）双层 1 和内消旋连接的卟啉 2，可用于生物学上重要的糖类路易斯寡糖的变构结合。由于硼酸-二醇相互作用，化合物 1 在水性介质中与路易斯寡糖结合，但由于 sigmoidal [寡糖] 与 [复杂] 等温线的关系，复合事件只能在高于临界浓度时发生。化合物1与Lewis低聚糖(K=10(5)-10(6)M(-2))具有足够高的亲和力，Hill系数n为1.8-2.0，Lewis(X)系列和Lewis(a)系列给出相反，对称的 CD 光谱。这是路易斯寡糖与人工受体有效结合的第一个例子，这已通过正同向变构成为可能。

  DOI：

  10.1021/ja010806e
• 作为产物：
  描述：

  4-甲酰基苯硼酸 、 1,3-丙二醇 以 甲苯 为溶剂， 反应 5.0h， 以100%的产率得到4-(1,3,2-dioxaborinan-2-yl)-benzaldehyde
  参考文献：
  名称：

  Extraction of Photogenerated Electrons and Holes from a Covalent Organic Framework Integrated Heterojunction

  摘要：

  Covalent organic frameworks (COFs) offer a strategy to position molecular semiconductors within a rigid network in a highly controlled and predictable manner. The pi-stacked columns of layered two-dimensional COFs enable electronic interactions between the COF sheets, thereby providing a path for exciton and charge carrier migration. Frameworks comprising two electronically separated subunits can form highly defined interdigitated donor-acceptor heterojunctions, which can drive the photogeneration of free charge carriers. Here we report the first example of a photovoltaic device that utilizes exclusively a crystalline organic framework with an inherent type II heterojunction as the active layer. The newly developed triphenylene-porphyrin COF was grown as an oriented thin film with the donor and acceptor units forming one-dimensional stacks that extend along the substrate normal, thus providing an optimal geometry for charge carrier transport. As a result of the degree of morphological precision that can be achieved with COFs and the enormous diversity of functional molecular building blocks that can be used to construct the frameworks, these materials show great potential as model systems for organic heterojunctions and might ultimately provide an alternative to the current disordered bulk heterojunctions.

  DOI：

  10.1021/ja509551m

文献信息

• Copper-Promoted <i>N</i>-Arylations of Cyclic Imides within Six-Membered Rings:  A Facile Route to Arylene-Based Organic Materials
  作者：Erin T. Chernick、Michael J. Ahrens、Karl A. Scheidt、Michael R. Wasielewski

  DOI：10.1021/jo0481351

  日期：2005.2.1

  oxygen atmosphere with gentle heating. Until now, the synthesis of N-arylated cyclic imides having six-membered rings was restricted largely to strongly heating anilines in the presence of anhydrides. This reaction is applicable to the synthesis of new organic materials based on arylene imide and bis(imide) dyes, such as perylene-3,4:9,10-bis(dicarboximide)s.

  显示在六元环内的环状酰亚胺在胺碱和氧气气氛下，在温和加热下，使用由乙酸铜（II）介导的各种芳基硼酸酯进行有效的N-芳基化。迄今为止，具有六元环的N-芳基化环状酰亚胺的合成主要限于在酸酐存在下强力加热苯胺。该反应适用于合成基于亚芳基酰亚胺和双（酰亚胺）染料的新有机材料，例如per 3,4：9,10-双（二甲酰亚胺）。
• Meso–meso-linked porphyrin dimer as a novel scaffold for the selective binding of oligosaccharides
  作者：Masato Ikeda、Seiji Shinkai、Atsuhiro Osuka

  DOI：10.1039/b003365k

  日期：——

  A meso–meso-linked porphyrin dimer 1 bearing four boronic acid groups shows high selectivity for maltotetraose (n = 4) among maltooligosaccharides (n = 1–7), indicating that this class of porphyrins acts as a novel scaffold to design oligosaccharide receptors.

  在麦芽寡糖（n = 1â7）中，含有四个硼酸基团的中链卟啉二聚体 1 对麦芽四糖（n = 4）具有很高的选择性，这表明这类卟啉是设计寡糖受体的新型支架。
• Porphyrin-based two-dimensional covalent organic frameworks: synchronized synthetic control of macroscopic structures and pore parameters
  作者：Xiao Feng、Long Chen、Yuping Dong、Donglin Jiang

  DOI：10.1039/c0cc04386a

  日期：——

  A two-dimensional porphyrin covalent organic framework is solvothermally synthesized and the macroscopic structure and pore parameters can be synthetically controlled. A remarkable and positive COF size effect on the pore parameters enables such structural control with a synchronized feature.

  二维卟啉共价有机框架通过溶剂热合成，宏观结构和孔参数可以被合成控制。COF对孔参数的显著而积极的尺寸效应使得这种结构控制具有同步特征。
• A-D-A Sensors Based on Naphthoimidazoledione and Boronic Acid as Turn-On Cyanide Probes in Water
  作者：Matinee Jamkratoke、Vithaya Ruangpornvisuti、Gamolwan Tumcharern、Thawatchai Tuntulani、Boosayarat Tomapatanaget

  DOI：10.1021/jo900170r

  日期：2009.5.15

  Three fluorescence sensors based on naphthoquinoneimidazole and boronic acid (A-D-A system) have been developed with high selectivity for cyanide in water. The fluorescence band at 460 nm was switched on upon substitution of cyanide on sensors in the CTAB micelle.
• Extraction of Photogenerated Electrons and Holes from a Covalent Organic Framework Integrated Heterojunction
  作者：Mona Calik、Florian Auras、Laura M. Salonen、Kathrin Bader、Irene Grill、Matthias Handloser、Dana D. Medina、Mirjam Dogru、Florian Löbermann、Dirk Trauner、Achim Hartschuh、Thomas Bein

  DOI：10.1021/ja509551m

  日期：2014.12.24

  Covalent organic frameworks (COFs) offer a strategy to position molecular semiconductors within a rigid network in a highly controlled and predictable manner. The pi-stacked columns of layered two-dimensional COFs enable electronic interactions between the COF sheets, thereby providing a path for exciton and charge carrier migration. Frameworks comprising two electronically separated subunits can form highly defined interdigitated donor-acceptor heterojunctions, which can drive the photogeneration of free charge carriers. Here we report the first example of a photovoltaic device that utilizes exclusively a crystalline organic framework with an inherent type II heterojunction as the active layer. The newly developed triphenylene-porphyrin COF was grown as an oriented thin film with the donor and acceptor units forming one-dimensional stacks that extend along the substrate normal, thus providing an optimal geometry for charge carrier transport. As a result of the degree of morphological precision that can be achieved with COFs and the enormous diversity of functional molecular building blocks that can be used to construct the frameworks, these materials show great potential as model systems for organic heterojunctions and might ultimately provide an alternative to the current disordered bulk heterojunctions.