NDI-双C8C12-双噻吩-双溴 | 1178586-27-0

• 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
• 中文名称: NDI-双C8C12-双噻吩-双溴
• 英文名称: N,N′-bis(2-octyldodecyl)-2,6-bis(5-bromothiophenyl-5-yl)-1,4,5,8-naphthalene diimide
• 英文别名: N,N'-bis(2-octyldodecyl)-2,6-bis(5-bromothiophen-2-yl)-1,4,5,8-naphthalene diimide；N,N'-bis(2-octyldodecyl)-2,6-bis(5-bromo-thiophenyl-5-yl)-1,4,5,8-naphthalene diimide；2,6-bis(2-bromothien-5-yl)naphthalene-1,4,5,8-tetracarboxylic-N,N'-bis(2-octyldodecyl) diimide；4,9-Bis(5-bromo-2-thienyl)-2,7-bis(2-octyldodecyl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone；2,9-bis(5-bromothiophen-2-yl)-6,13-bis(2-octyldodecyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 1178586-27-0
• 化学式: C₆₂H₈₈Br₂N₂O₄S₂
• 分子量: 1149.33
• InChiKey: AMBLANUJLYJBOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.1
• 重原子数：
  72
• 可旋转键数：
  38
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  NDI-双C8C12-双噻吩-双溴 、 锌 以 四氢呋喃 为溶剂， 以0%的产率得到
  参考文献：
  名称：

  Chain-Growth Polymerization of Unusual Anion-Radical Monomers Based on Naphthalene Diimide: A New Route to Well-Defined n-Type Conjugated Copolymers

  摘要：

  Strongly electron-deficient (n-type) main-chain g-conjugated polymers are commonly prepared via well-established step-growth polycondensation protocols which enable limited control over polymerization. Here we demonstrate that activated Zn and electron-deficient brominated thiophene-naphthalene diimide oligomers form anion-radical complexes instead of conventional Zn-organic derivatives. These highly unusual zinc complexes undergo Ni-catalyzed chain-growth polymerization leading to n-type conjugated polymers with controlled molecular weight, relatively narrow polydispersities, and specific end-functions.

  DOI：

  10.1021/ja208710x
• 作为产物：
  描述：

  1,4,5,8-萘四甲酸酐 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 1,3-二溴-5,5-二甲基海因 、 硫酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 44.0h， 生成 NDI-双C8C12-双噻吩-双溴
  参考文献：
  名称：

  基于萘二酰亚胺 (NDI) 的 π 共轭聚合物的分子封装：了解光致发光的工具

  摘要：

  本文展示了一种新颖的合成策略，可用于以前所未有的精度调整共轭聚合物之间的链间距离。该控制为从根本上了解 NDI 聚合物的固态光学特性提供了一个理想的平台。

  DOI：

  10.1002/anie.202110139

文献信息

• Semiconducting Compounds and Devices Incorporating Same
  申请人：Watson Mark D.

  公开号：US20100252112A1

  公开（公告）日：2010-10-07

  Disclosed are semiconducting compounds having one or more phthalimide units and/or one or more head-to-head (H-H) substituted biheteroaryl units. Such compounds can be monomeric, oligomeric, or polymeric, and can exhibit desirable electronic properties and possess processing advantages including solution-processability and/or good stability at ambient conditions.

  本文披露了具有一个或多个邻苯二酰亚胺单元和/或一个或多个头-头（H-H）取代的双杂环芳基单元的半导体化合物。这些化合物可以是单体、寡聚体或聚合物，可以表现出理想的电子性能，并具有处理优势，包括可溶性处理和/或在常温条件下良好的稳定性。
• Effect of alkyl-chain branching position on nanoscale morphology and performance of all-polymer solar cells
  作者：Fangbin Liu、Hui Li、Chunling Gu、Hongbing Fu

  DOI：10.1039/c4ra13351j

  日期：——

  The improved performance of an all-polymer solar cell was attributed to the well-ordered structure of polymer C3 and nanoscale phase separation in a blend film of the polymer, which resulted from manipulating the alkyl-chain branching position of the polymer.

  一种全聚合物太阳能电池的性能提高归因于聚合物C3的有序结构和聚合物混合膜中的纳米级相分离，这是通过调控聚合物的烷基侧链分支位置实现的。
• Naphthalene diimide and benzothiadiazole copolymer acceptor for all-polymer solar cells with improved open-circuit voltage and morphology
  作者：Fangbin Liu、Hui Li、Yishi Wu、Chunling Gu、Hongbing Fu

  DOI：10.1039/c5ra14887a

  日期：——

  Donor–acceptor (D–A) copolymers PNDIBTH and PNDIBTOC8 based on two strong electron-deficient units, naphthalene diimide and benzothiadiazole, were synthesized and used as acceptors for the fabrication of all-polymer solar cells (all-PSCs). Introduction of the two octyloxy side chains onto the benzothiadiazole in PNDIBTOC8 could not only increase the solubility and molecular weight of the polymer, but

  合成了基于两个强电子缺陷单元萘二酰亚胺和苯并噻二唑的施主-受主（DA）共聚物PNDIBTH和PNDIBTOC8，并将其用作制造全聚合物太阳能电池（all-PSC）的受主。将两个辛氧基侧链引入PNDIBTOC8中的苯并噻二唑不仅可以增加聚合物的溶解度和分子量，而且可以改变其光学和电子性能。与PNDIBTH相比，PNDIBTOC8具有更高的分子量，并将LUMO水平提高至-3.72 eV。使用聚合物PBDTTT-CT作为供体材料对两种PSC中的两种聚合物的光伏性能进行的研究表明，PNDIBTOC8具有3.14％的出色功率转换效率（PCE），且具有高开路电压（V oc）为0.90 V，远高于基于PNDIBTH的器件（PCE为1.20％，V oc为0.76 V）。而且，基于PNDIBTOC8的共混膜中的类树突状相分离有助于高和更平衡的电荷迁移率。
• Highly Planarized Naphthalene Diimide–Bifuran Copolymers with Unexpected Charge Transport Performance
  作者：Rukiya Matsidik、Alessandro Luzio、Özge Askin、Daniele Fazzi、Alessandro Sepe、Ullrich Steiner、Hartmut Komber、Mario Caironi、Michael Sommer

  DOI：10.1021/acs.chemmater.6b05313

  日期：2017.7.11

  The synthesis, characterization, and charge transport performance of novel copolymers PNDIFu2 made from alternating naphthalene diimide (NDI) and bifuran (Fu2) units are reported. Usage of potentially biomass-derived Fu2 as alternating repeat unit enables flattened polymer backbones due to reduced steric interactions between the imide oxygens and Fu2 units, as seen by density functional theory (DFT)

  报告了由交替的萘二酰亚胺（NDI）和双呋喃（Fu2）单元制成的新型共聚物PNDIFu2的合成，表征和电荷传输性能。如密度泛函理论（DFT）计算和UV-vis光谱学所见，由于酰亚胺氧与Fu2单元之间的空间相互作用减少，潜在地使用生物质衍生的Fu2作为交替重复单元可以使聚合物主链变平。与在所有溶剂和所探测温度下发生的类似NDI-联噻吩（T2）共聚物PNDIT2相比，PNDIFu2在溶液中的聚集作用得以增强。与PNDIT2看到的0.39 nm相比，PNDIFu2的π-π堆积距离更小，为0.35 nm。薄膜中聚集体的对准是通过使用偏心旋涂实现的，2 /（V s）。尽管增强了主链平面性，较小的π-π堆积和增强的电荷传输各向异性，但PNDIFu2的电子迁移率比PNDIT2低约三倍。密度泛函理论计算表明，与PNDIT2相比，PNDIFu2中的电荷传输受到极化子定位增强的限制。
• Naphthalenediimide-Benzothiadiazole Copolymer Semiconductors: Rational Molecular Design for Air-Stable Ambipolar Charge Transport
  作者：Chunling Gu、Wenping Hu、Jiannian Yao、Hongbing Fu

  DOI：10.1021/cm401122h

  日期：2013.5.28

  Rational design of air-stable ambipolar polymeric semiconductors was achieved by covalently connecting naphthalenediimide (NDI) units with benzothiadiazole (BZ) through thiophene (T) linkers, namely, PNDI-mT(BZ)mT (m = 1, 2), in which well-coplanar mT(BZ)mT moieties as a whole act as donors rather than acceptors reported in previous studies. Decreasing the number of thiophene linkers from m = 2 to 1 lowers both LUMO and HOMO energy levels. As a result, the carriers in organic thin film transistors (OTFTs) could be switched from unipolar p-channel only to ambipolar transport. In ambient conditions, PNDI-2T(BZ)2T presents an average hole mobility of 0.07 +/- 0.02 cm(2) V-1 s(-1), while PNDI-T(BZ) T exhibits balanced ambipolar charge transport in a bottom-gate/top-contact device architecture, the average electron and hole mobilities was 0.05 +/- 0.02 (mu(e)) and 0.1 +/- 0.03 (mu(h)) cm(2) V-1 s(-1), respectively. Moreover, OTFTs based on both polymer show good air-stability with negligible changes after stored in ambient over 3 months.