1,5-dimethoxynaphthalene-2,6-dicarboxaldehyde | 151807-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5-dimethoxynaphthalene-2,6-dicarboxaldehyde
• 英文别名: 4,8-dimethoxynaphthalene-2,6-dicarboxaldehyde；1,5-dimethoxy-2,6-diformylnaphthalene；1,5-Dimethoxynaphthalene-2,6-dicarbaldehyde
• CAS: 151807-70-4
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: YFDVPXNDBKIIJV-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C
• 沸点：
  455.7±40.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-dimethoxynaphthalene-2,6-dicarboxaldehyde 在 aluminum (III) chloride 、 叔丁基锂 、 potassium carbonate 作用下， 以 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 3,7-dibromo-1,5-bis(2-ethylhexyloxy)-naphthalene-2,6-dicarbaldehyde
  参考文献：
  名称：

  Synthesis and Characterization of a Novel Naphthodithiophene-Based Copolymer for Use in Polymer Solar Cells

  摘要：

  A novel naphtho[2,3-b:6,7-d']dithiophene (NDT)-based copolymer, poly[4,9-bis(2-ethylhexyloxy)naphtho[2,3-b:6,7-d']dithiophene-2,7-diyl-alt-1,3-(5-heptadecan-9-yl)-4H-thieno[3,4-c]pyrrole-4,6-dione] (P1), was synthesized and characterized for use in polymer solar cells. We systematically investigated the synthesis, thermal stability, optical and electrochemical properties, field-effect carrier mobilities, and photovoltaic characteristics of the resulting polymer. The properties of the NDT-based polymer were compared with those of poly[4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene-alt-1,3-(5-heptadecan-9-yl)-4H-thieno[3,4-c]pyrrole-4,6-dione] (P2) prepared via the same synthetic procedure. Polymer solar cells made from the new polymer, P1, yielded a power conversion efficiency of 4.0% with a short-circuit current density of 11.54 mA/cm(2), an open-circuit voltage of 0.69 V, and a fill factor of 0.50 under AM 1.5 G irradiation (100 mW/cm(2)).

  DOI：

  10.1021/ma301312d
• 作为产物：
  描述：

  1,5-二甲氧基萘 在 正丁基锂 、 溴 作用下， 以 二氯甲烷 为溶剂， 生成 1,5-dimethoxynaphthalene-2,6-dicarboxaldehyde
  参考文献：
  名称：

  Preparation of Some 4,8-Dimethoxy-diformylnaphthalenes

  摘要：

  Dibromination of 1,5-dimethoxynaphthalene ( 1 ) yields three different dibromo-1,5-dimethoxynaphthalenes. These are converted to 1,5-dimethoxynaphtalenedicarbaldehydes.

  DOI：

  10.1080/00397919308011292

文献信息

• Tuning the size of macrocyclic cavities in trianglimine macrocycles
  作者：Nikolai Kuhnert、Nicolai Burzlaff、Chirag Patel、Ana Lopez-Periago

  DOI：10.1039/b417941b

  日期：——

  The synthesis of aromatic dicarboxaldehydes is described along with their reactivity in the [3 + 3] cyclocondensation reaction with (1R,2R)-diaminocyclohexane to give trianglimine macrocycles. In particular, the scope and limitation of the reaction with regard to complete control of the cavity size of the macrocycles is discussed producing a total of 11 macrocycles with different cavity sizes ranging from 9 to 23 Å.

  本文介绍了芳香族二甲醛的合成过程，以及它们与 (1R,2R)- 二氨基环己烷发生 [3 + 3] 环缩合反应生成三醯亚胺大环的反应性。特别是讨论了该反应在完全控制大环空腔尺寸方面的范围和局限性，总共生成了 11 个空腔尺寸从 9 Å 到 23 Å 不等的大环。
• Synthesis, X-ray Structure, and Electrochemical Oxidative Coupling Reactions of 1,5- and 2,6-Bis(1,4-dithiafulven-6-yl)naphthalenes
  作者：Susana González、Nazario Martín、Luis Sánchez、José L. Segura、Carlos Seoane、Isabel Fonseca、Félix H. Cano、Josep Sedó、José Vidal-Gancedo、Concepció Rovira

  DOI：10.1021/jo982261l

  日期：1999.5.1

  tetrathiafulvalene (TTF) derivatives (12a-c, 13a-c, 15a-c) in which the two 1,3-dithiole units are connected through a naphthalene spacer have been prepared in high yields by Wittig-Horner olefination reaction from dialkoxy-substituted diformylnaphthalenes (11a,b, 14) and differently substituted phosphonate esters (10a-c). The electrochemical study revealed a similar behavior for the novel electron donor

  通过维蒂希-霍纳（Wittig-Horner）烯烃化反应以高收率制备了新颖的π-延伸的四硫富瓦烯（TTF）衍生物（12a-c，13a-c，15a-c），其中两个1,3-二硫醇单元通过萘间隔基连接。由二烷氧基取代的二甲酰基萘（11a，b，14）和不同取代的膦酸酯（10a-c）制得。电化学研究表明，无论萘核上1,3-二硫醇环的位置如何，新型电子给体分子（12a-c，13a-c，15a-c）的行为都相似。延伸的供体经历了有效的电氧化过程，提供了新的低聚延伸的TTF物质，该新的低聚物的延伸的TTF物质显示出比其前体供体更低的氧化电位值。EPR实验证实了源自低聚TTF乙烯基化合物的阳离子自由基的存在，并支持ECE过程。通过对12a的X射线分析和半经验的PM3计算进行了结构研究，结果表明，由于萘部分与硫富瓦烯环形成约35度的角，其平面度出现了扭曲的几何形状。实验值和计算值之间找到了很好的一致性，从而验
• Preparation of Some 4,8-Dimethoxy-diformylnaphthalenes
  作者：Kristian Sylvester-Hvid、Jeanett S⊘rensen⊘rensen、Kjeld Schaumburg、Klaus Bechgaard、J⊘rn B. Christensen

  DOI：10.1080/00397919308011292

  日期：1993.7

  Dibromination of 1,5-dimethoxynaphthalene ( 1 ) yields three different dibromo-1,5-dimethoxynaphthalenes. These are converted to 1,5-dimethoxynaphtalenedicarbaldehydes.
• Synthesis and Characterization of a Novel Naphthodithiophene-Based Copolymer for Use in Polymer Solar Cells
  作者：Sanjaykumar S R、Sachin Badgujar、Chang Eun Song、Won Suk Shin、Sang-Jin Moon、In-Nam Kang、Jaemin Lee、Shinuk Cho、Sang Kyu Lee、Jong-Cheol Lee

  DOI：10.1021/ma301312d

  日期：2012.9.11

  A novel naphtho[2,3-b:6,7-d']dithiophene (NDT)-based copolymer, poly[4,9-bis(2-ethylhexyloxy)naphtho[2,3-b:6,7-d']dithiophene-2,7-diyl-alt-1,3-(5-heptadecan-9-yl)-4H-thieno[3,4-c]pyrrole-4,6-dione] (P1), was synthesized and characterized for use in polymer solar cells. We systematically investigated the synthesis, thermal stability, optical and electrochemical properties, field-effect carrier mobilities, and photovoltaic characteristics of the resulting polymer. The properties of the NDT-based polymer were compared with those of poly[4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene-alt-1,3-(5-heptadecan-9-yl)-4H-thieno[3,4-c]pyrrole-4,6-dione] (P2) prepared via the same synthetic procedure. Polymer solar cells made from the new polymer, P1, yielded a power conversion efficiency of 4.0% with a short-circuit current density of 11.54 mA/cm(2), an open-circuit voltage of 0.69 V, and a fill factor of 0.50 under AM 1.5 G irradiation (100 mW/cm(2)).