4,5,9,10-四溴-2,7-二(2-癸基十四烷基)苯并[LMN][3,8]邻二氮杂菲-1,3,6,8(2H,7H)-四酮 | 1219501-16-2

• 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: 4,5,9,10-四溴-2,7-二(2-癸基十四烷基)苯并[LMN][3,8]邻二氮杂菲-1,3,6,8(2H,7H)-四酮
• 英文名称: 4,5,9,10-tetrabromo-2,7-bis(2-decyltetradecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
• 英文别名: N,N'-di(2-decyltetradecyl)-2,3,6,7-tetrabromonaphthalenetetracarboxylic acid diimide；N,N'-di(2-decyltetradecyl)-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic acid diimide；4,5,9,10-Tetrabromo-2,7-bis(2-decyltetradecyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone；2,3,9,10-tetrabromo-6,13-bis(2-decyltetradecyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1,3,8,10,15-pentaene-5,7,12,14-tetrone
• CAS: 1219501-16-2
• 化学式: C₆₂H₉₈Br₄N₂O₄
• 分子量: 1255.09
• InChiKey: DTBBPSMVMRGXKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  27.5
• 重原子数：
  72
• 可旋转键数：
  44
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  4,5,9,10-四溴-2,7-二(2-癸基十四烷基)苯并[LMN][3,8]邻二氮杂菲-1,3,6,8(2H,7H)-四酮 在 potassium carbonate 、 lead dioxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 14,29-Bis(2-decyltetradecyl)-3,10-dithia-14,18,25,29-tetrazaoctacyclo[14.14.2.02,11.04,9.012,32.017,26.019,24.027,31]dotriaconta-1,4,6,8,11,16(32),17,19,21,23,25,27(31)-dodecaene-13,15,28,30-tetrone
  参考文献：
  名称：

  Synthesis and Properties of Heterocyclic Acene Diimides

  摘要：

  A series of heterocyclic acene diimides were synthesized effectively based on the condensation of o-phenylenediamine, 1,2-benzenedithiol, and 2-aminothiophenol with 2,3,6,7-tetrabromo-1,4,5,8-naphthalene tetracarboxylic diimide. The diimides exhibit interesting optical and electrical properties with one of them showing a hole mobility up to 0.02 cm(2) V-1 s(-1).

  DOI：

  10.1021/ol303551p
• 作为产物：
  描述：

  2-癸基十四烷基-1-胺 、 四(4-甲酰基苯基)硅烷 在 溶剂黄146 、 三溴化磷 作用下， 以 甲苯 为溶剂， 以19%的产率得到4,5,9,10-四溴-2,7-二(2-癸基十四烷基)苯并[LMN][3,8]邻二氮杂菲-1,3,6,8(2H,7H)-四酮
  参考文献：
  名称：

  与 2-(1,3-Dithiol-2-Ylidene) 丙腈基团融合的纤芯扩展萘二酰亚胺，用于高性能、环境稳定、溶液处理的 n 沟道有机薄膜晶体管

  摘要：

  报道了一类用于有机薄膜晶体管 (OTFT) 的新型 n 型半导体，其基于与 2-(1,3-二硫醇-2-亚基) 丙腈基团稠合的核扩展萘二酰亚胺。这些物种的前两个代表源自长支化 N-烷基链，已成功用作高性能、环境稳定、溶液处理的 n 沟道 OTFT 的活性层。他们通过旋涂方法制造的底部栅极顶部接触器件表现出高达 0.51 cm(2) V(-1) s(-1) 的高电子迁移率，电流开/关比为 10(5)-10( 7)，以及在环境条件下低于 10 V 的小阈值电压。由于这类 n 型有机半导体具有相对较低的 LUMO 能级和良好的成膜能力，因此即使长时间暴露于环境空气中，它们也表现出良好的环境稳定性。

  DOI：

  10.1021/ja910667y

文献信息

• Core-Expanded Naphthalene Diimides Fused with Sulfur Heterocycles and End-Capped with Electron-Withdrawing Groups for Air-Stable Solution-Processed n-Channel Organic Thin Film Transistors
  作者：Yunbin Hu、Xike Gao、Chong-an Di、Xiaodi Yang、Feng Zhang、Yunqi Liu、Hongxiang Li、Daoben Zhu

  DOI：10.1021/cm102850j

  日期：2011.3.8

  present compounds bear the branched N-alkyl substituents with the carbon atom numbers from 12 to 24, which guarantees good material solubility. The solution-processed, bottom-gate organic thin film transistors based on new compounds 3−12 operate well in air with the electron mobility ranging from ∼10−6 to 0.26 cm2 V−1 s−1, depending on the nature of the branched N-alkyl substituent and the π-backbone

  芯膨胀的萘二酰亚胺的四个家族（NDI）衍生物，设计并合成，即，NDI-DTYM2（1 - 7，其中1和2以前报道），NDI-DTDCN2（8和9），NDI-DTYCA2（10和11），以及NDI-DCT2（12），其中NDI核融合了两个2-（1,3-二硫醇-2-亚甲基）丙二腈（DTYM）基团，两个1,4-二硫氨酸-2,3-二碳腈（DTDCN）基团，两个烷基2-（1 ，3-二硫基-2-亚烷基）氰基乙酸酯（DTYCA）基团和两个2，3-二氰基噻吩（DCT）基团。本发明化合物的NDI核心带有碳原子数为12至24的支链N-烷基取代基，这保证了良好的材料溶解性。的溶液处理，底栅有机薄膜基于新化合物晶体管3 - 12与空气中的电子迁移率范围为〜10操作以及-6至0.26厘米2 V -1小号-1，取决于的性质支链的N-烷基取代基和π-主链结构。
• Sulfur Containing Heterocycle-Fused Naphthalene Tetracarboxylic Acid Diimide Derivatives, Preparation Method And Use Thereof
  申请人：Gao Xike

  公开号：US20120253045A1

  公开（公告）日：2012-10-04

  Sulfur containing heterocycle-fused naphthalenetetracarboxylic acid diimide derivatives represented by formula (I) are disclosed, in which, R 1 and R 2 are C 1 -C 30 and C 1 -C 12 linear alkyl or branched alkyl, respectively; R 3 is H or halogen atom. The preparation method of the derivatives and the use thereof in manufacture of organic thin film field effect transistor or organic solar batteries are also disclosed.

  公开了由式(I)表示的含硫杂环融合萘四羧酸二亚胺衍生物，其中，R1和R2分别为C1-C30和C1-C12的线性或支链烷基；R3为H或卤素原子。还公开了这些衍生物的制备方法以及它们在制造有机薄膜场效应晶体管或有机太阳能电池中的用途。
• [EN] PHOTOTHERMAL AGENTS<br/>[FR] AGENTS PHOTOTHERMIQUES
  申请人：UNIV HONG KONG SCI & TECH

  公开号：WO2020015700A1

  公开（公告）日：2020-01-23

  A photothermal agent can be used in both photoacoustic imaging (PAI) and photothermal therapy (PTT) applications. The photothermal agent can include a small molecule, organic compound and/or polymers with absorption in the near-infrared (NIR) interrogation window (700-900 nm). The compound can be a biocompatible organic nanoparticle (ONP). The photothermal agent can be administered to a patient to locate a tumor site in the patient using in vivo imaging techniques. Once the tumor site has been determined, the tumor site can be irradiated with near-infrared light to stop or inhibit the growth of the tumor.

  光热剂可以用于光声成像（PAI）和光热疗法（PTT）应用中。光热剂可以包括在近红外（NIR）探测窗口（700-900 nm）中吸收的小分子、有机化合物和/或聚合物。该化合物可以是生物相容的有机纳米粒子（ONP）。光热剂可以被注入患者体内，利用体内成像技术定位患者的肿瘤部位。一旦确定了肿瘤部位，就可以用近红外光照射肿瘤部位，以停止或抑制肿瘤的生长。
• SULFUR CONTAINING HETEROCYCLE-FUSED NAPHTHALENE TETRACARBOXYLIC ACID DIIMIDE DERIVATIVES, PREPARATION METHOD AND USE THEREOF
  申请人：Shanghai Institute Of Organic Chemistry, Chinese Academy Of Sciences

  公开号：EP2492271B1

  公开（公告）日：2018-05-09
• Conjugated donor-acceptor copolymers from dicyanated naphthalene diimide
  作者：Liu Yang、Chengyi Xiao、Wei Jiang、Zhaohui Wang

  DOI：10.1016/j.tet.2014.04.002

  日期：2014.9

  A series of donor-acceptor (D-A) alternating copolymers including P(2CNNDI-T), P(2CNNDI-TT), P(2CNNDI-BT), and P(2CNNDI-BDT) based on dicyanated naphthalene diimide (2CN-NDI) in backbones were presented and characterized in this contribution. Their structures were unambiguously identified by NMR spectra. Optical and electrochemical measurements revealed that their LUMO energy levels are substantially lowered at about -4.4 eV by the substitution of electron-deficient cyano groups on the backbone of as-synthesized polymers. And the HOMO levels varied from -6.15 eV to -5.70 eV as a reflection of electron-donating ability of combined thiophene derivatives. The moderate electron-transporting characteristics under ambient conditions based on these dicyanated polymers indicated their promising applications as air-stable electron transporting semiconductors in future electronics. (C) 2014 Elsevier Ltd. All rights reserved.