24-二羟基-135-均苯三甲醛 | 58343-11-6

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 24-二羟基-135-均苯三甲醛
• 英文名称: 2,4-dihydroxybenzene-1,3,5-tricarbaldehyde
• 英文别名: resorcinol-2,4,6-tricarboxaldehyde；2,4,6-triformylresorcinol；DHTA；Resorcin-2,4,6-tricarbaldehyd
• CAS: 58343-11-6
• 化学式: C₉H₆O₅
• 分子量: 194.144
• InChiKey: CEPNDKRJQPJVNM-UHFFFAOYSA-N

物化性质

• 熔点：
  215-217 °C
• 沸点：
  252.5±40.0 °C(Predicted)
• 密度：
  1.600±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-氨基蒽 、 24-二羟基-135-均苯三甲醛 以 乙醇 为溶剂， 反应 24.0h， 以75%的产率得到
  参考文献：
  名称：

  Anthracene-Resorcinol Derived Covalent Organic Framework as Flexible White Light Emitter

  摘要：

  The ordered modular structure of a covalent organic framework (COF) facilitates the selective incorporation of electronically active segments that can be tuned to function cooperatively. This designability inspires developing COF-based single-source white light emitters, required in next-generation solid-state lighting. Here, we present a new anthracene-resorcinol-based COF exhibiting white light emission. The keto-enol tautomers present in the COF give rise to dual emission, which can be tuned by the O-donor and N-donor solvents. Importantly, when suspended in a solid polymer matrix, this dual emission is retained as both tautomers coexist. A mere 0.32 wt % loading of the COF in poly(methyl methacrylate) (PMMA) gives a solvent-free film with intense white light emission (CIE coordinates (0.35, 0.36)). From steady-state and time-resolved studies, the mechanism of the white light emission has been unambiguously assigned to fluorescence, with the blue emission originating from the pi-stacked columns of anthracene, and the mixture of red and green from the keto-enol tautomerized resorcinol units. The study introduces the COF as a new class of readily processable, single-source white light emitter.

  DOI：

  10.1021/jacs.8b08312
• 作为产物：
  描述：

  2,4,6-tris-(1,3-diphenyl-imidazolidin-2-yl)-benzene-1,3-diol 在 盐酸 、 水 作用下， 反应 2.0h， 以96%的产率得到24-二羟基-135-均苯三甲醛
  参考文献：
  名称：

  N-(2,4-DIFORMYL-5-HYDROXYPHENYL)ACETAMIDE

  摘要：

  DOI：

  10.15227/orgsyn.060.0049

文献信息

• Large-scale synthesis of azine-linked covalent organic frameworks in water and promoted by water
  作者：Jian Lu、Feng Lin、Qiang Wen、Qiao-Yan Qi、Jia-Qiang Xu、Xin Zhao

  DOI：10.1039/c9nj00830f

  日期：——

  hydrothermal procedure has been developed to produce azine-linked COFs by conducting condensation reactions of hydrazine with hydroxy-substituted 1,3,5-triformylbenzene in water. The synthesis of one representative COF was drastically promoted by water in comparison with the traditional solvothermal reactions in organic solvents. This synthesis has advantages of large-scale production, catalyst-free

  通过在水中使肼与羟基取代的1,3,5-三甲酰基苯进行缩合反应，已经开发了一种水热方法来生产与嗪连接的COF。与在有机溶剂中的传统溶剂热反应相比，水可显着促进一种代表性COF的合成。该合成具有大规模生产，无催化剂反应，反应时间短的优点，并且所获得的COF具有较高的结晶度和表面积。
• [EN] COVALENT ORGANIC FRAMEWORK AND METHODS OF FABRICATION AND USES THEREOF<br/>[FR] ÉDIFICE ORGANIQUE COVALENT ET SES PROCÉDÉS DE PRÉPARATION ET UTILISATIONS ASSOCIÉES
  申请人：NAT UNIV SINGAPORE

  公开号：WO2020214095A1

  公开（公告）日：2020-10-22

  The present invention relates to, in general, methods of fabricating a covalent organic framework (COF) and the COF thereof. In particular, the method comprises forming an acylhydrazone bond with an optionally substituted 2-alkoxybenzohydrazidyl moiety. The resultant COF has an x-ray diffraction 2-theta peak at about 3˚ with a full width half maximum (FWHM) of about 0.2˚ to about 0.4˚.

  本发明涉及一般用于制造共价有机框架（COF）及其COF的方法。具体而言，该方法包括使用可选取代的2-烷氧基苯甲酰肼基团形成酰肼酸酯键。所得的COF在x射线衍射2θ峰处约为3˚，其全峰宽半高度（FWHM）约为0.2˚至0.4˚。
• Formylation of phenols using formamidine acetate
  作者：S. Hessam M. Mehr、Hannah Depmeier、Katsuya Fukuyama、Mahboobeh Maghami、Mark J. MacLachlan

  DOI：10.1039/c6ob02727j

  日期：——

  We report a new method to formylate phenol derivatives using formamidine acetate and acetic anhydride. This general-purpose transformation is a significant improvement over many other methods and does not require high temperatures or the addition of strong acid or base. Mono-, di-, and tri-formylated product can be obtained, depending on the substrate and conditions used.

  我们报告了一种使用乙酸form和乙酸酐对苯酚衍生物进行甲酰化的新方法。这种通用转化是对许多其他方法的重大改进，不需要高温或添加强酸或强碱。根据所用的底物和条件，可以获得单，二和三甲酰化产物。
• Acridine‐Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C−N Cross‐Coupling
  作者：Michael Traxler、Sebastian Gisbertz、Pradip Pachfule、Johannes Schmidt、Jérôme Roeser、Susanne Reischauer、Jabor Rabeah、Bartholomäus Pieber、Arne Thomas

  DOI：10.1002/anie.202117738

  日期：2022.5.16

  A new family of porous crystalline COFs bearing acridine moieties was synthesized and applied as photocatalysts in metallaphotocatalytic C−N cross-coupling. Among these materials the fully β-ketoenamine-linked COF showed the highest catalytic activity and was shown to be recyclable and even catalyzed the cross-coupling efficiently under green light irradiation.

  合成了一个新的带有吖啶部分的多孔晶体COF家族，并将其用作金属光催化CN交叉偶联中的光催化剂。在这些材料中，完全β-酮烯胺连接的COF表现出最高的催化活性，并且可回收，甚至在绿光照射下有效催化交叉偶联。
• Programmable Photocatalytic Activity of Multicomponent Covalent Organic Frameworks Used as Metallaphotocatalysts
  作者：Michael Traxler、Susanne Reischauer、Sarah Vogl、Jérôme Roeser、Jabor Rabeah、Christopher Penschke、Peter Saalfrank、Bartholomäus Pieber、Arne Thomas

  DOI：10.1002/chem.202202967

  日期：2023.1.18

  Various multicomponent COFs bearing both a moiety for photosensitization and complexation of nickel catalysts were synthesized using reticulation with different 1,3,5-triformylbenzene nodes. This enabled the switching between persistent, charge-separated species or efficient charge-carrier mobility for different metallaphotocatalytic cross-coupling reactions based on the node unit. The frameworks showed

  使用具有不同 1,3,5-三甲酰苯节点的网状结构合成了多种多组分 COF，这些 COF 具有光敏化部分和镍催化剂的络合部分。这使得基于节点单元的不同金属光催化交叉偶联反应能够在持久的、电荷分离的物种或有效的电荷载流子迁移率之间切换。这些框架显示出可回收性和使用红光照射驱动反应的可能性。