1,2-二(癸基氧基)-4,5-二碘苯 | 155259-28-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1,2-二(癸基氧基)-4,5-二碘苯
• 英文名称: 1,2-bis(decyloxy)-4,5-diiodobenzene
• 英文别名: 4,5-Didecenoxy-1,2-diiodobenzene；1,2-didecyloxy-4,5-diiodobenzene；4,5-Bis(decyloxy)-1,2-diiodobenzene；1,2-didecoxy-4,5-diiodobenzene
• CAS: 155259-28-2
• 化学式: C₂₆H₄₄I₂O₂
• 分子量: 642.443
• InChiKey: OCOUOTKNHUTKJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-二(癸基氧基)-4,5-二碘苯 在 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Effect of Phthalimide in 2,1,3-Benzooxadiazole Based Copolymer on the Performances of Solar Cells

  摘要：

  Two newly designed donor-acceptor (D-A) conjugated polymers were prepared from the Stille coupling reactions by incorporating phthalimide derivative as a co-acceptor unit into 2,1,3-benzooxadiazole (BO) and thiophene with different ratios of 5mol.% and 10mol.% of TBO-I 5, TBO-I 10, respectively. Polymers possess moderate molecular weights and excellent thermal properties with a 5% weight loss temperatures (T-d) around 300 degrees C. Compared to poly{5,6-bis(decyloxy)-4-(thiophen-2-yl)benzo[c][1,2,5]oxadiazole} (TBO), adding phthalimide unit in TBO-I 5 and TBO-I 10 shifted UV-Vis absorption spectra and changed the HOMO and LUMO levels of polymers. Bulk hetero junction (BHJ) polymer solar cells (PSCs) based on polymers blended with [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) were fabricated to investigate photovoltaic properties. As a results, with increasing the composition of phthalimide, the J(sc) of the devices based on polymers were reduced in the order of TBO (4.74mA/cm(2)) > TBO-I 5 (3.94mA/cm(2)) > TBO-I 10 (1.90mA/cm(2)) due to the blue-shifted in absorption spectra and twisting in polymer main chain of TBO-I polymers. The decrease in J(sc) led to low photovoltaic performances and the device based on TBO showed higher performances than those of TBO-I 5 and TBO-I 10 with the PCE of 1.66%, the J(sc) of 4.74mA/cm(2), the V-oc of 0.82V and the FF of 42.4% under the illumination of AM 1.5G, 100 mW/cm(2).

  DOI：

  10.1080/15421406.2014.933383
• 作为产物：
  描述：

  癸基溴 在 硫酸 、 碘 、 碘酸 、 sodium hydroxide 作用下， 以 甲醇 、 四氯化碳 为溶剂， 生成 1,2-二(癸基氧基)-4,5-二碘苯
  参考文献：
  名称：

  Effect of Phthalimide in 2,1,3-Benzooxadiazole Based Copolymer on the Performances of Solar Cells

  摘要：

  Two newly designed donor-acceptor (D-A) conjugated polymers were prepared from the Stille coupling reactions by incorporating phthalimide derivative as a co-acceptor unit into 2,1,3-benzooxadiazole (BO) and thiophene with different ratios of 5mol.% and 10mol.% of TBO-I 5, TBO-I 10, respectively. Polymers possess moderate molecular weights and excellent thermal properties with a 5% weight loss temperatures (T-d) around 300 degrees C. Compared to poly{5,6-bis(decyloxy)-4-(thiophen-2-yl)benzo[c][1,2,5]oxadiazole} (TBO), adding phthalimide unit in TBO-I 5 and TBO-I 10 shifted UV-Vis absorption spectra and changed the HOMO and LUMO levels of polymers. Bulk hetero junction (BHJ) polymer solar cells (PSCs) based on polymers blended with [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) were fabricated to investigate photovoltaic properties. As a results, with increasing the composition of phthalimide, the J(sc) of the devices based on polymers were reduced in the order of TBO (4.74mA/cm(2)) > TBO-I 5 (3.94mA/cm(2)) > TBO-I 10 (1.90mA/cm(2)) due to the blue-shifted in absorption spectra and twisting in polymer main chain of TBO-I polymers. The decrease in J(sc) led to low photovoltaic performances and the device based on TBO showed higher performances than those of TBO-I 5 and TBO-I 10 with the PCE of 1.66%, the J(sc) of 4.74mA/cm(2), the V-oc of 0.82V and the FF of 42.4% under the illumination of AM 1.5G, 100 mW/cm(2).

  DOI：

  10.1080/15421406.2014.933383

文献信息

• Synthesis, Spectroscopic and Nonlinear Optical Properties of Multiple [60]Fullerene-Oligo(p-phenylene ethynylene) Hybrids
  作者：Yuming Zhao、Yasuhiro Shirai、Aaron D. Slepkov、Long Cheng、Lawrence B. Alemany、Takashi Sasaki、Frank A. Hegmann、James M. Tour

  DOI：10.1002/chem.200401198

  日期：2005.6.6

  spectroscopic and cyclic voltammetry (CV) experiments. Our studies clearly show that although the multiple [60]fullerene groups are connected via pi-conjugated OPE frameworks, they present diminutive electronic interactions in the ground state, and the electronic behavior of the [60]fullerene cages are only affected by the OPE backbones through modest inductive effects. Interestingly, sizable third-order

  通过一种新开发的原位乙炔化方法，合成了一系列多个[60]富勒烯封端的低聚（对亚苯基乙炔基）（OPE）杂化化合物。通过1D和2D NMR光谱分析表征了高度不饱和的富碳C（60）和OPE支架的结构和磁屏蔽性能。[60]富勒烯与OPE骨架之间的电子相互作用通过UV / Vis光谱和循环伏安法（CV）实验进行了研究。我们的研究清楚地表明，尽管多个[60]富勒烯基团通过pi共轭OPE框架连接，但它们在基态下呈现出微小的电子相互作用，并且[60]富勒烯笼的电子行为仅受OPE主链影响通过适度的感应效应。有趣的是，确定了相对于其OPE前驱体的多富勒烯-OPE杂化体31的较大的三阶非线性光学（NLO）响应（γ）和增强的双光子吸收（TPA）截面（sigma（（2）））。克尔效应（DOKE）实验。这种增强的NLO性能大概是由于在激发态中发生过共轭和/或电荷转移效应。另外，观察到了OPE五聚体12的相对强的激发态
• 2D Networks of Rhombic-Shaped Fused Dehydrobenzo[12]annulenes: Structural Variations under Concentration Control
  作者：Kazukuni Tahara、Satoshi Okuhata、Jinne Adisoejoso、Shengbin Lei、Takumi Fujita、Steven De Feyter、Yoshito Tobe

  DOI：10.1021/ja904481j

  日期：2009.12.9

  rhombic-shaped bisDBA derivatives 1a-d, 2a, and 2b were synthesized for the purpose of the formation of porous networks at the 1,2,4-trichlorobenzene (TCB)/graphite interface. Depending on the alkyl-chain length and the solute concentration, bisDBAs exhibit five network structures, three porous structures (porous A, B, and C), and two nonporous structures (nonporous D and E), which are attributed to their rhombic

  为了在 1,2,4-三氯苯 (TCB)/石墨界面形成多孔网络，合成了一系列烷基和烷氧基取代的菱形双 DBA 衍生物 1a-d、2a 和 2b。根据烷基链长度和溶质浓度，双 DBA 表现出五种网络结构、三种多孔结构（多孔 A、B 和 C）和两种无孔结构（无孔 D 和 E），这归因于它们的菱形核形状和取代基的位置。具有较短烷基链的 BisDBA 1a 和 1b 有利于形成多孔结构，而具有较长烷基链的双 DBA 1c 和 1d 倾向于形成无孔结构。然而，稀释后，无孔结构通常会转化为多孔结构，这一趋势可以通过表面覆盖率、分子密度、和系统焓的分子间相互作用。此外，多孔结构通过溶剂分子的共吸附而稳定。至少在某种程度上，所有化合物都形成了最有趣的多孔结构 Kagome 模式，其三角形和六边形孔的大小可以通过烷基链长度进行调整。本研究证明，浓度控制是在液固界面构建多孔网络的强大而通用的工具。其三角形和六边
• Two-Dimensional Porous Molecular Networks of Dehydrobenzo[12]annulene Derivatives via Alkyl Chain Interdigitation
  作者：Kazukuni Tahara、Shuhei Furukawa、Hiroshi Uji-i、Tsutomu Uchino、Tomoyuki Ichikawa、Jian Zhang、Wael Mamdouh、Motohiro Sonoda、Frans C. De Schryver、Steven De Feyter、Yoshito Tobe

  DOI：10.1021/ja0655441

  日期：2006.12.1

  physisorption from 1,2,4-trichlorobenzene (TCB) onto highly oriented pyrolytic graphite (HOPG). Under similar experimental conditions, DBA 2a shows the formation of a honeycomb network. The core symmetry and location of alkyl substituents determine the network structure. The most remarkable feature of the DBA networks is the interdigitation of the nonpolar alkyl chains: they connect the pi-conjugated cores and

  一系列六氢三苯并 [12] 环烯 (DBA) 衍生物的自组装已通过液固界面的扫描隧道显微镜 (STM) 进行了仔细检查。首先，通过比较菱形 bisDBA 1a 和三角形 DBA 2a 的二维 (2D) 排序来研究核心对称性对网络结构的影响（图 1）。BisDBA 1a 在从 1,2,4-三氯苯 (TCB) 物理吸附到高度取向的热解石墨 (HOPG) 后形成 Kagomé 网络。在类似的实验条件下，DBA 2a 显示了蜂窝网络的形成。烷基取代基的核心对称性和位置决定了网络结构。DBA 网络最显着的特征是非极性烷基链的相互交叉：它们连接 pi 共轭核并引导它们的方向。因此，形成具有空隙的二维开放网络。其次，研究了烷基链长度对 DBA 模式结构的影响。在增加烷基链（DBA 3c-e）的长度后，在 TCB 中观察到从蜂窝网络到线性网络的转变，这种观察归因于更强的分子 - 底物相互作用。第三，在四种不同的溶剂中研究了溶剂对非极性
• Trapping a pentagonal molecule in a self-assembled molecular network: an alkoxylated isosceles triangular molecule does the job
  作者：Masaru Anzai、Masahiko Iyoda、Steven De Feyter、Yoshito Tobe、Kazukuni Tahara

  DOI：10.1039/d0cc01823f

  日期：——

  [5]meta-phenyleneacetylene [5]CMPA, is trapped by the adaptive supramolecular network formed by an isosceles triangular molecule, alkoxy substituted dehydrobenzo[14]annulene [14]ISODBA at the liquid/graphite interface, leading to a highly ordered and large-area bicomponent self-assembled molecular network (SAMN), as revealed by scanning tunneling microscopy (STM).

  我们在此报告表面自适应自组装的独特示例。五边形大环环状[5]-亚苯基乙炔[5] CMPA，被等腰三角形分子，烷氧基取代的脱氢苯并[14]环戊烯[14] ISODBA在液体/石墨界面处形成的自适应超分子网络捕获，扫描隧道显微镜（STM）揭示了导致高度有序的大面积双组分自组装分子网络（SAMN）。
• Synthesis of Diacetylene Macrocycles Derived from 1,2-Diethynyl Benzene Derivatives: Structure and Reactivity of the Strained Cyclic Dimer
  作者：Qin Zhou、Patrick J. Carroll、Timothy M. Swager

  DOI：10.1021/jo00085a016

  日期：1994.3

  Diacetylene macrocycles 2-4 (n = 1-3) (R = H, C4H9, C6H13, C10H21, C12H25, OC10H21) have been prepared from the oxidative coupling of 1,2-diethynylbenzene derivatives. These compounds can be produced in useful quantities and are of interest as precursors to novel conjugated organic polymers. The reported results indicate that when the R groups are large the dimeric macrocycle (n = 1) can be prepared in as high as 74% yield from the corresponding 1,2-diethynylbenzene in a one-step procedure. An alternate multistep procedure was found to produce the tetrameric macrocycle (n = 3, R = C6H13) in 45 % yield. The highly strained dimeric macrocycle was characterized by an X-ray structure and was found to be very reactive. The dimers undergo a rapid very exothermic polymerization at 100-125-degrees-C, indicative of a chain reaction. Reaction of the dimeric macrocycles with iodine results in intramolecular cyclization and a new 20pi electron tetraiodide fused ring system. Reaction of the tetraiodide with oxygen produces a related compound in which two of the iodides have been converted to ketones.