2,7-bis(6-hydroxyhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone | 214892-62-3

• 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: 2,7-bis(6-hydroxyhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
• 英文别名: N,N'-bis[6-hydroxyhexyl]naphthalene-1,4,5,8-tetracarboxydiimide；6,13-Bis(6-hydroxyhexyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone；6,13-bis(6-hydroxyhexyl)-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: 214892-62-3
• 化学式: C₂₆H₃₀N₂O₆
• 分子量: 466.534
• InChiKey: VHOLXESDUWATJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,7-bis(6-hydroxyhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone 在 吡啶 、 四氮唑 、 4-二甲氨基吡啶 作用下， 生成 Diisopropyl-phosphoramidous acid 6-(7-{6-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-hexyl}-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl)-hexyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  稳定短DNA双链体的端盖。

  摘要：

  描述了用于共价连接平末端双链DNA的3'和5'羟基的端帽的合成。封端二醇被转化为DMTr保护的亚磷酰胺，并掺入到自互补八聚体的核苷酸4和5之间。通过Tm实验对自互补八聚体测定端帽对双链DNA的稳定作用。

  DOI：

  10.1081/ncn-120023088
• 作为产物：
  描述：

  6-氨基-1-己醇 、 1,4,5,8-萘四甲酸酐 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以55%的产率得到2,7-bis(6-hydroxyhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
  参考文献：
  名称：

  Anion induced displacement studies in naphthalene diimide containing interpenetrated and interlocked structures

  摘要：

  这篇文章介绍了对能够通过位移检测或分子运动来感知阴离子的超分子系统的开发研究。研究表明，缺电子的萘二亚胺线和富含电子的间苯二甲酰胺萘氢醌大环可形成有色的假紫杉烷组装体。研究人员对这种互穿系统以比色法感知阴离子的能力进行了调查。阴离子与大环的间苯二甲酰胺基团发生络合，导致萘二亚胺线位移，从而失去颜色。然而，在相应的轮烷结构中，萘二亚胺轴与大循环轮的萘氢醌基团之间的机械结合强度增强，从而抵消了阴离子引起的位移过程。

  DOI：

  10.1039/b819322c

文献信息

• Anion induced displacement studies in naphthalene diimide containing interpenetrated and interlocked structures
  作者：Kathleen M. Mullen、Jason J. Davis、Paul D. Beer

  DOI：10.1039/b819322c

  日期：——

  This article describes investigations into the development of supramolecular systems capable of sensing anions through either displacement type assays or molecular motion. An electron deficient naphthalene diimide thread and an electron rich isophthalamide naphthohydroquinone macrocycle were shown to form a coloured pseudorotaxane assembly. Investigations into the ability of such interpenetrated systems to sense anions colorimetrically were undertaken. Anion complexation at the isophthalamide group of the macrocycle causes displacement of the naphthodiimide thread resulting in the loss of colour. The enhanced mechanically bonded binding strength between the naphthodiimide axle and the naphthohydroquinone groups of the macrocycle wheel in the corresponding rotaxane structure, however, was found to negate the anion induced displacement process.

  这篇文章介绍了对能够通过位移检测或分子运动来感知阴离子的超分子系统的开发研究。研究表明，缺电子的萘二亚胺线和富含电子的间苯二甲酰胺萘氢醌大环可形成有色的假紫杉烷组装体。研究人员对这种互穿系统以比色法感知阴离子的能力进行了调查。阴离子与大环的间苯二甲酰胺基团发生络合，导致萘二亚胺线位移，从而失去颜色。然而，在相应的轮烷结构中，萘二亚胺轴与大循环轮的萘氢醌基团之间的机械结合强度增强，从而抵消了阴离子引起的位移过程。
• Structure engineering of naphthalene diimides for improved charge carrier mobility: self-assembly by hydrogen bonding, good or bad?
  作者：Nagesh B. Kolhe、R. Nandini Devi、Satyaprasad P. Senanayak、B. Jancy、K. S. Narayan、S. K. Asha

  DOI：10.1039/c2jm32554c

  日期：——

  Two families of naphthalene diimide (NDI) derivatives were compared and contrasted for the effect of self-assembly on charge carrier transport. One series of NDI derivatives had a terminal phenyl ring attached to a hexyl spacer substituted naphthalene core either through an ester or an amide linkage (NDI-E and NDI-A, respectively), while the other series had a 3,4,5-tridodecyloxy phenyl unit (NDI-E3, NDI-A3) instead of the terminal phenyl unit. Solution processed thin films of these molecules exhibited n-type charge transport characteristics in a bottom gate top contact organic field effect transistor (OFET) geometry. The amide derivatives showed evidence of self-organization with observation of red shifted aggregate emission in solution as well as solid state. Variable temperature FTIR studies in the solid state confirmed the existence of strong hydrogen bonding which could be broken only at very high temperature. However, contrary to expectations, the NDI ester derivatives showed better device efficiency with electron mobilities in the range 8.5 × 10−3 to 2 × 10−2 cm2 V−1 s−1 and on/off ratio ∼104. The thin film crystallinity and morphology of NDI-E and NDI-A were examined through X-ray diffraction and atomic force microscopy (AFM). The correlation of crystallinity, hydrogen bonding and charge carrier mobility was studied using energy minimized structures from density functional theory (DFT). The higher electron mobility of ester linked NDI derivatives over the amide linked ones was attributed to the freedom in charge transport pathways offered by a three dimensional crystalline organization in the ester compared to the restricted directional hydrogen bonding interaction in the amide derivatives.

  我们比较了两个系列的萘二亚胺（NDI）衍生物，并对比了自组装对电荷载流子传输的影响。其中一个系列的 NDI 衍生物具有一个末端苯基环，通过酯或酰胺连接（分别为 NDI-E 和 NDI-A）到一个己基间隔取代的萘核；而另一个系列的 NDI 衍生物则具有一个 3,4,5-十三烷氧基苯基单元（NDI-E3、NDI-A3），而不是末端苯基单元。这些分子的溶液加工薄膜在底栅顶部接触有机场效应晶体管（OFET）几何结构中表现出 n 型电荷传输特性。酰胺衍生物在溶液和固态下都能观察到红移聚合发射，显示出自组织的证据。固态下的变温傅立叶变换红外光谱研究证实了强氢键的存在，这种氢键只有在很高的温度下才能断开。然而，与预期相反的是，NDI 酯衍生物显示出更高的器件效率，电子迁移率在 8.5 × 10-3 到 2 × 10-2 cm2 V-1 s-1 之间，开/关比为 ∼104。通过 X 射线衍射和原子力显微镜（AFM）研究了 NDI-E 和 NDI-A 的薄膜结晶度和形貌。利用密度泛函理论（DFT）的能量最小化结构研究了结晶度、氢键和电荷载流子迁移率的相关性。与酰胺连接的 NDI 衍生物相比，酯连接的 NDI 衍生物具有更高的电子迁移率，这是因为与酰胺衍生物中受限的定向氢键相互作用相比，酯的三维结晶组织提供了电荷传输路径的自由度。
• Diazabicyclic Electroactive Ionenes for Efficient and Stable Organic Solar Cells
  作者：Zuhao You、Yanan Song、Wenxu Liu、Wenlong Wang、Chenghao Zhu、Yuxin Duan、Yao Liu

  DOI：10.1002/anie.202302538

  日期：——

  Diazabicyclic electroactive ionenes with high density of interfacial dipoles are developed as interlayers in organic solar cells. Devices containing the optimal electroactive ionene interlayer give efficiency up to 18.43 % and excellent operational stability with exceptional interlayer thickness tolerance over 100 nm.

  具有高密度界面偶极子的二氮杂双环电活性紫罗烯被开发为有机太阳能电池的夹层。包含最佳电活性紫罗烯夹层的器件可提供高达 18.43% 的效率和出色的操作稳定性，夹层厚度公差超过 100 nm。
• Naphthalenetetracarboxylic Diimide-Based n-Channel Transistor Semiconductors:  Structural Variation and Thiol-Enhanced Gold Contacts
  作者：Howard E. Katz、Jerainne Johnson、Andrew J. Lovinger、Wenjie Li

  DOI：10.1021/ja000870g

  日期：2000.8.1

  The synthesis and field-effect transistor (FET) electron mobility of ten N-substituted naphthalene 1,4,5,8-tetracarboxylic diimide (NTCDI) derivatives deposited at ambient and elevated temperatures are reported. Mobilities >0.01 cm(2)/(V s) were measured in air for three NTCDIs with partially fluorinated substituents, and >0.001 cm(2)/V s) for a hydroxy-terminated compound. Mobilities 0.001-0.1 cm(2)/(V s) were also found for three n-alkyl NTCDIs, but only under vacuum; FET operation with gold bottom contacts was enabled by specific thiol coatings of the contacts. The highest mobility in air, >0.1 cm(2)/(V s), was conferred by 4-trifluoromethylbenzyl substitution, while 1H,1H-perfluorooctyl substitution resulted in an on/off ratio in air 10(5). Solution electrochemistry and solid-state X-ray and electron diffraction were employed to partially explain the results, and applications of the materials to complementary circuits. are considered.
• Endcaps for Stabilizing Short DNA Duplexes
  作者：Pei-Sze Ng、Maneesh R. Pingle、Ganesan Balasundarum、Alan Friedman、Xiaolin Zu、Donald E. Bergstrom

  DOI：10.1081/ncn-120023088

  日期：2003.10

  double-stranded DNA are described. Endcap diols were converted into DMTr protected phosphoramidites and incorporated between nucleotides 4 and 5 of a self-complementary octamer. The stabilizing effect of the endcaps on duplex DNA was determined by Tm experiments on the self-complementary octamer.

  描述了用于共价连接平末端双链DNA的3'和5'羟基的端帽的合成。封端二醇被转化为DMTr保护的亚磷酰胺，并掺入到自互补八聚体的核苷酸4和5之间。通过Tm实验对自互补八聚体测定端帽对双链DNA的稳定作用。