1,5-dihydroxynaphthalene-2,6-dicarboxaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5-dihydroxynaphthalene-2,6-dicarboxaldehyde
• 英文别名: 1,5-Dihydroxynaphthalene-2,6-dicarbaldehyde；1,5-dihydroxynaphthalene-2,6-dicarbaldehyde
• 化学式: C₁₂H₈O₄
• 分子量: 216.193
• InChiKey: QELJVWMKHYSBOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-dihydroxynaphthalene-2,6-dicarboxaldehyde 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Highly Fluorescent Red-Light Emitting Bis(boranils) Based on Naphthalene Backbone

  摘要：

  Ten bis(boranils) differently substituted at the boron atom and iminophenyl groups were synthesized from 1,5-dihydroxynaphthalene-2,6-dicarboxaldehyde using a simple one-pot protocol. Their photophysical properties can be easily tuned in a wide range by the variation of substituents. Their absorption and emission spectral bands are significantly red-shifted (lambda(max) = 495590 nm, lambda(em) = 533683 nm) when compared with simple boranils, whereas fluorescence quantum yields are strongly improved to reach 83%. The attachment of pendant NO2 and NEt2 groups at the opposite positions of the pi-conjugated bis(boranil) scaffold resulted in the formation of an unprecedented system featuring push-pull architecture.

  DOI：

  10.1021/acs.joc.7b01001
• 作为产物：
  描述：

  1,5-二羟基萘 在 盐酸 、 正丁基锂 、 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 16.5h， 生成 1,5-dihydroxynaphthalene-2,6-dicarboxaldehyde
  参考文献：
  名称：

  Highly Fluorescent Red-Light Emitting Bis(boranils) Based on Naphthalene Backbone

  摘要：

  Ten bis(boranils) differently substituted at the boron atom and iminophenyl groups were synthesized from 1,5-dihydroxynaphthalene-2,6-dicarboxaldehyde using a simple one-pot protocol. Their photophysical properties can be easily tuned in a wide range by the variation of substituents. Their absorption and emission spectral bands are significantly red-shifted (lambda(max) = 495590 nm, lambda(em) = 533683 nm) when compared with simple boranils, whereas fluorescence quantum yields are strongly improved to reach 83%. The attachment of pendant NO2 and NEt2 groups at the opposite positions of the pi-conjugated bis(boranil) scaffold resulted in the formation of an unprecedented system featuring push-pull architecture.

  DOI：

  10.1021/acs.joc.7b01001

文献信息

• The effect of locking π-conjugation in organoboron moieties in the structures of luminescent tetracoordinate boron complexes
  作者：Mateusz Urban、Krzysztof Durka、Patrycja Górka、Gabriela Wiosna-Sałyga、Krzysztof Nawara、Piotr Jankowski、Sergiusz Luliński

  DOI：10.1039/c9dt01332f

  日期：——

  the spiro geometry of the boron atom, borafluorene and ligand units are perpendicularly aligned, which considerably affects the flexibility of the molecule as well as its solid-state structure. Through comparative analysis with close diphenyl analogues, we show how these structural features influence the thermal, photoluminescent and charge mobility behaviour of the studied compounds. Crystal structural

  为了阐明有机硼部分的刚性化对这些化合物的物理化学性质的影响，在实验和理论上对一系列的8种发光的硼芴配合物进行了广泛的研究。由于硼原子的螺线几何形状，硼芴和配体单元垂直排列，这极大地影响了分子的柔性及其固态结构。通过与紧密的二苯基类似物进行比较分析，我们显示了这些结构特征如何影响所研究化合物的热，光致发光和电荷迁移行为。晶体结构分析表明，这些分子主要通过垂直排列的硼芴与相邻分子的配体部分之间形成的C–H⋯O和C–H⋯π相互作用连接，分别充当电子密度的互补供体和受体。这也有效地防止了分子参与不利的π堆积接触。此外，结构分析表明，由于OBN杂环畸变和相互的硼芴-配体平面运动，硼硼烷络合物具有相当程度的柔韧性。这些效应的大小严格取决于配体结构，并可能导致相对于BPh的量子产率增加或降低 结构分析表明，由于OBN杂环畸变和相互之间的硼芴配体平面运动，硼芴配合物具有相当程度的灵活性。这些效应的大小严格
• Highly Crystalline and Semiconducting Imine‐Based Two‐Dimensional Polymers Enabled by Interfacial Synthesis
  作者：Hafeesudeen Sahabudeen、Haoyuan Qi、Marco Ballabio、Miroslav Položij、Selina Olthof、Rishi Shivhare、Yu Jing、SangWook Park、Kejun Liu、Tao Zhang、Ji Ma、Bernd Rellinghaus、Stefan Mannsfeld、Thomas Heine、Mischa Bonn、Enrique Cánovas、Zhikun Zheng、Ute Kaiser、Renhao Dong、Xinliang Feng

  DOI：10.1002/anie.201915217

  日期：2020.4.6

  multi-layer 2D polyimine films have been achieved through interfacial synthesis methods. However, it remains a great challenge to achieve the maximum degree of crystallinity in the 2D polyimines, which largely limits the long-range transport properties. Here we employ a surfactant-monolayer-assisted interfacial synthesis (SMAIS) method for the successful preparation of porphyrin and triazine containing polyimine-based

  通过界面合成方法已经获得了单层和多层2D聚亚胺膜。但是，在2D多亚胺中实现最大程度的结晶度仍然是一个巨大的挑战，这在很大程度上限制了远程传输性能。在这里，我们采用表面活性剂单层辅助界面合成（SMAIS）方法成功地分别制备了具有正方形和六角形晶格的含卟啉和三嗪的聚亚胺基2D聚合物（PI-2DP）膜。合成PI-2DP薄膜具有多晶多层膜，其可调厚度范围为6至200 nm，并且具有较大的晶畴（尺寸为100-150 nm）。被高结晶度和电活性卟啉部分的存在所吸引，通过时间分辨太赫兹光谱研究了PI-2DP的光电性能。通常，基于卟啉的PI-2DP 1膜具有p型半导体行为，其带隙为1.38 eV，空穴迁移率高达0.01 cm2 V-1 s-1，优于先前报道的基于聚亚胺的材料。
• Hashemi, Mohammed M.; Balalaie, Saeed, Journal of Chemical Research - Part S, 1996, # 3, p. 170 - 171
  作者：Hashemi, Mohammed M.、Balalaie, Saeed

  DOI：——

  日期：——
• Spectral and quantum-chemical investigation of ortho- and peri-hydroxy-substituted mono- and diformyl derivatives of 1,5-naphthalenediol
  作者：V. V. Mezheritskii、M. S. Korobov、O. M. Golyanskaya、N. I. Omelichkin、L. G. Minyaeva、G. S. Borodkin、A. A. Milov、A. V. Tsukanov、A. D. Dubonosov

  DOI：10.1134/s1070428012020233

  日期：2012.2

  Spectral and quantum-chemical investigation of ortho- and peri-hydroxy-substituted aldehydes, 1,5-naphthalenediol derivatives, was carried out. An unusual spin-spin coupling through an intramolecular hydrogen bond was discovered in the molecule of 1,5-dihydroxynaphthalene-4,8-dicarbaldehyde. It was shown that this dialdehyde is involved into the ring-chain tautomerism. The position of this equilibrium was examined depending on the temperature and the solvent polarity. The effect of the solvent polarity on the benzoid-quinoid tautomerism in the dihydroxynaphthalene-2,6-dicarbaldehyde was established. By the method of quantum-chemical calculations the relative energy stability and conformational structure of dialdehydes were revealed.
• Highly Fluorescent Red-Light Emitting Bis(boranils) Based on Naphthalene Backbone
  作者：Mateusz Urban、Krzysztof Durka、Piotr Jankowski、Janusz Serwatowski、Sergiusz Luliński

  DOI：10.1021/acs.joc.7b01001

  日期：2017.8.4

  Ten bis(boranils) differently substituted at the boron atom and iminophenyl groups were synthesized from 1,5-dihydroxynaphthalene-2,6-dicarboxaldehyde using a simple one-pot protocol. Their photophysical properties can be easily tuned in a wide range by the variation of substituents. Their absorption and emission spectral bands are significantly red-shifted (lambda(max) = 495590 nm, lambda(em) = 533683 nm) when compared with simple boranils, whereas fluorescence quantum yields are strongly improved to reach 83%. The attachment of pendant NO2 and NEt2 groups at the opposite positions of the pi-conjugated bis(boranil) scaffold resulted in the formation of an unprecedented system featuring push-pull architecture.