1,5-bis(methoxymethoxy)-2,6-dibromonaphthalene | 1187021-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5-bis(methoxymethoxy)-2,6-dibromonaphthalene
• 英文别名: 2,6-dibromo-1,5-bis(methoxymethoxy)naphthalene
• CAS: 1187021-38-0
• 化学式: C₁₄H₁₄Br₂O₄
• 分子量: 406.071
• InChiKey: ZAQOEZUUBQVMAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,5-bis(methoxymethoxy)-2,6-dibromonaphthalene 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 31.5h， 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 溴 、 sodium hydride 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 9.0h， 生成 1,5-bis(methoxymethoxy)-2,6-dibromonaphthalene
  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

• Single-Crystal Organic Field-Effect Transistors of Naphthodifurans
  作者：Chikahiko Mitsui、Junshi Soeda、Kazumoto Miwa、Kazutaka Shoyama、Yoshinori Ota、Hayato Tsuji、Jun Takeya、Eiichi Nakamura

  DOI：10.1246/bcsj.20150033

  日期：2015.6.15

  Three types of naphthodifurans (NDFs) have been designed as active organic materials in organic field-effect transistors (OFETs), and one of them, naphtho[2,1-b:6,5-b′]difuran, has been found to show an excellent OFET mobility of up to 3.6 cm2 V−1 s−1. Based on the crystal-packing structure and theoretical analyses, we attribute the high carrier mobility of the NDF derivatives to large intermolecular interactions and small reorganization energies. The NDF compounds show very high thermal and electrochemical stability. Together with some previous studies, the present study indicates that fused furan compounds show a performance that is equal to or better than that of the corresponding thiophene compounds.

  三种类型的萘并二呋喃 (NDF) 被设计为有机场效应晶体管 (OFET) 中的活性有机材料，其中一种萘并[2,1-b:6,5-b']二呋喃被发现可以显示出高达 3.6 cm2 V−1 s−1 的出色 OFET 迁移率。基于晶体堆积结构和理论分析，我们将NDF衍生物的高载流子迁移率归因于大的分子间相互作用和小的重组能。 NDF 化合物表现出非常高的热稳定性和电化学稳定性。结合之前的一些研究，本研究表明稠合呋喃化合物的性能等于或优于相应的噻吩化合物。
• 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。
• Mori, Keiji; Ohmori, Ken; Suzuki, Keisuke, Angewandte Chemie - International Edition, 2009, vol. 48, p. 5638 - 5641
  作者：Mori, Keiji、Ohmori, Ken、Suzuki, Keisuke

  DOI：——

  日期：——