N,N'-di(n-hexyl)-2-tri(n-buty)lstannylnaphthalene-1,4,5,8-bis(dicarboximide) | 1355362-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N'-di(n-hexyl)-2-tri(n-buty)lstannylnaphthalene-1,4,5,8-bis(dicarboximide)
• 英文别名: N,N'-di-n-hexyl-2-(tri-n-butylstannyl)naphthalene-1,8:4,5-bis(dicarboximide)
• CAS: 1355362-11-6
• 化学式: C₃₈H₅₆N₂O₄Sn
• 分子量: 723.584
• InChiKey: DDXCLFXWYOSSSC-UHFFFAOYSA-N

物化性质

• 沸点：
  736.3±70.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.25
• 重原子数：
  45
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-di(n-hexyl)-2-tri(n-buty)lstannylnaphthalene-1,4,5,8-bis(dicarboximide) 、 2,7-dibromo-benzo[1,2-b:6,5-b']dithiophene-4-one-5-(1,3-dioxolane) 在 四(三苯基膦)钯 、 copper(II) iodide 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以51.6%的产率得到2-[2'-(6,13-Dihexyl-5,7,12,14-tetraoxo-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1,3,8(16),9,11(15)-pentaen-2-yl)-5'-oxospiro[1,3-dioxolane-2,4'-thieno[3,2-g][1]benzothiole]-7'-yl]-6,13-dihexyl-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1,3,8(16),9,11(15)-pentaene-5,7,12,14-tetrone
  参考文献：
  名称：

  [EN] NAPHTHALENE-DIIMIDE-HETEROCYCLE-NAPHTHALENE DIIMIDE OLIGOMERS AS ORGANIC SEMICONDUCTORS AND TRANSISTORS THEREFROM
  [FR] OLIGOMÈRES DE NAPHTALÈNE DIIMIDE-HÉTÉROCYCLE-NAPHTALÈNE DIIMIDE EN TANT QUE SEMI-CONDUCTEURS ET TRANSISTORS ASSOCIÉS

  摘要：

  本文披露的各种发明和/或其实施例涉及某些萘二酰亚胺（NDI）化合物，其中NDI基固定在某些桥联杂芳基（hAr）类别上，例如“NDI-hAr-NDI”寡聚化合物，其中hAr是选择的杂芳基，以提供理想的电子和立体特性，并在此描述了“Rz”端部外围取代基团的可能身份。可以制备晶体管和反相器件。

  公开号：

  WO2012142460A1
• 作为产物：
  描述：

  1,4,5,8-萘四甲酸酐 在 tris-(dibenzylideneacetone)dipalladium(0) 、 硫酸 、 三(邻甲基苯基)磷 作用下， 以 甲苯 为溶剂， 反应 44.83h， 生成 N,N'-di(n-hexyl)-2-tri(n-buty)lstannylnaphthalene-1,4,5,8-bis(dicarboximide)
  参考文献：
  名称：

  [EN] REACTION PRODUCTS OF STANNYL DERIVATIVES OF NAPHTHALENE DIIMIDES WITH RYLENE COMPOUNDS
  [FR] PRODUITS RÉACTIONNELS DE DÉRIVÉS STANNYLIQUE DE NAPHTALÈNEDIIMIDES AVEC DES COMPOSÉS DE RYLÈNE

  摘要：

  NDI锡化合物与芳香烃化合物反应形成NDI-芳香烃化合物。芳香烃化合物可以是苝化合物。NDI-芳香烃化合物可用于有机电子器件，包括场效应晶体管。

  公开号：

  WO2013091279A1

文献信息

• Pyrrole[3,2-d:4,5-d′]bisthiazole-bridged bis(naphthalene diimide)s as electron-transport materials
  作者：Yulia A. Getmanenko、Sanjeev Singh、Bhupinder Sandhu、Cheng-Yin Wang、Tatiana Timofeeva、Bernard Kippelen、Seth R. Marder

  DOI：10.1039/c3tc31677g

  日期：——

  A series of materials with 2,6-disubstituted-N-alkyl-pyrrole[3,2-d:4,5-d′]bisthiazole (PBTz) with triisopropylsilyl- (TIPS), bromo- and naphthalene diimide (NDI) groups were synthesized. The electronic properties of 2,6-bis-TIPS- and 2,6-dibromo-N-hexyl-PBTz were studied by cyclic voltammetry and by density functional theory (DFT) calculations, and their solid-state packing was examined by the single crystal X-ray structural analysis. DFT calculations and the electrochemical data revealed that this core is both a weak donor and a weak acceptor. Small molecules with bis(NDI)-substituted N-alkyl-PBTz architecture were studied by differential pulse voltammetry, UV-vis absorption spectroscopy, and differential scanning calorimetry, and their electrical properties were examined in n-channel organic field-effect transistors using solution-processed films. The electron mobility value μe as high as 0.13 cm2 V−1 s−1 with a Ion/Ioff ratio of 5 × 105 and threshold voltage Vth = 4.9 V was observed for PBTz-bridged bis(naphthalene diimide) with hexyl chains on pyrrole and NDI nitrogen atoms, while the material with longer dodecyl groups showed μe up to 0.19 cm2 V−1 s−1 with a Ion/Ioff ratio of 7 × 104 and Vth = 7.9 V in a 1 : 1 polystyrene matrix. Finally, compounds with electron-withdrawing acetyl groups at position 6 of the NDI units were examined by electrochemistry and in OFET configurations.

  一系列具有三异丙基硅基 (TIPS)、溴和萘二酰亚胺 (NDI) 基团的 2,6-二取代-N-烷基-吡咯[3,2-d:4,5-d']双噻唑 (PBTz) 材料被合成。通过循环伏安法和密度泛函理论 (DFT) 计算研究了 2,6-双-TIPS 和 2,6-二溴-N-己基-PBTz 的电子性质，并通过单晶 X 射线结构分析检查了它们在固态下的堆积情况。DFT 计算和电化学数据显示该核心既是一个弱供体，也是一个弱受体。通过差分脉冲伏安法、紫外-可见吸收光谱和差示扫描量热法研究了具有双(NDI)-取代的 N-烷基-PBTz 结构的小分子，并通过溶液法制备的薄膜在 n 沟道有机场效应晶体管中检查了它们的电学性质。对于在吡咯和 NDI 氮原子上带有己基链的 PBTz-桥联的双(萘二酰亚胺)，观察到高达 0.13 cm² V⁻¹ s⁻¹ 的电子迁移率 μe，电流开启/关闭比为 5 × 10⁵，阈值电压 Vth = 4.9 V，而在 1:1 聚苯乙烯基质中，带有更长十二烷基基团的材料的 μe 高达 0.19 cm² V⁻¹ s⁻¹，电流开启/关闭比为 7 × 10⁴，Vth = 7.9 V。最后，在 NDI 单元的 6 位带有吸电子乙酰基的化合物通过电化学和 OFET 配置进行了检查。
• Stannyl Derivatives of Naphthalene Diimides and Their Use in Oligomer Synthesis
  作者：Lauren E. Polander、Alexander S. Romanov、Stephen Barlow、Do Kyung Hwang、Bernard Kippelen、Tatiana V. Timofeeva、Seth R. Marder

  DOI：10.1021/ol203432x

  日期：2012.2.3

  2-Stannyl and 2,6-distannyl naphthalene diimides (NDIs) can be synthesized through the palladium-catalyzed reaction of the appropriate bromo derivatives with hexabutylditin. The utility of these precursors in palladium catalyzed cross-coupling reactions is demonstrated by the synthesis of bi- and ter-NDI derivatives, UV-vis, cyclic voltammetry, and n-channel organic field-effect transistor data for which are compared to those of the monomeric parent NDI.
• Stable Solution-Processed Molecular<i>n</i>-Channel Organic Field-Effect Transistors
  作者：Do Kyung Hwang、Raghunath R. Dasari、Mathieu Fenoll、Valérie Alain-Rizzo、Amir Dindar、Jae Won Shim、Nabankur Deb、Canek Fuentes-Hernandez、Stephen Barlow、David G. Bucknall、Pierre Audebert、Seth R. Marder、Bernard Kippelen

  DOI：10.1002/adma.201201689

  日期：2012.8.22

  A new solution-processable small-molecule containing electron-poor naphthalene diimide and tetrazine moieties has been synthesized. The optimized spin-coated n-channel OFETs on glass substrate shows electron mobility value up to 0.15 cm(2) V(-1) s(-1) . Inkjet-printed OFETs are fabricated in ambient atmosphere on flexible plastic substrates, which exhibits an electron mobility value up to 0.17 cm(2) V(-1) s(-1) and also shows excellent environmental and operational stability.