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.
• [EN] REACTION PRODUCTS OF STANNYL DERIVATIVES OF NAPHTHALENE DIIMIDES WITH RYLENE COMPOUNDS<br/>[FR] PRODUITS RÉACTIONNELS DE DÉRIVÉS STANNYLIQUE DE NAPHTALÈNEDIIMIDES AVEC DES COMPOSÉS DE RYLÈNE
  申请人：CHINESE ACAD INST CHEMISTRY

  公开号：WO2013091279A1

  公开（公告）日：2013-06-27

  NDI-tin compounds are reacted with rylene compounds to form NDI-rylene compounds. The rylene compounds can be perylene compounds. The NDI-rylene compounds can be used in organic electronic devices including in a field-effect transistor.

  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。
• [EN] NAPHTHALENE-DIIMIDE-HETEROCYCLE-NAPHTHALENE DIIMIDE OLIGOMERS AS ORGANIC SEMICONDUCTORS AND TRANSISTORS THEREFROM<br/>[FR] OLIGOMÈRES DE NAPHTALÈNE DIIMIDE-HÉTÉROCYCLE-NAPHTALÈNE DIIMIDE EN TANT QUE SEMI-CONDUCTEURS ET TRANSISTORS ASSOCIÉS
  申请人：GEORGIA TECH RES INST

  公开号：WO2012142460A1

  公开（公告）日：2012-10-18

  The various inventions and/or their embodiments disclosed herein relate to certain naphthalene diimide (NDI) compounds wherein the NDI groups are bonded to certain subclasses of bridging heteroaryl (hAr) groups, such as the "NDI-hAr-NDI" oligomeric compounds, wherein hAr is a heteroaryl group chosen to provide desirable electronic and steric properties, and the possible identities of the "Rz" terminal peripheral substituent groups are described herein. Transistor and inverter devices can be prepared.

  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。