6,13-diphenyl-6,13-dihydropentacene-6,13-diol | 76727-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 6,13-diphenyl-6,13-dihydropentacene-6,13-diol
• 英文别名: 6,13-diphenyl-6,13-pentacenediol；6,13-diphenyl-6,13-dihydro-pentacene-6,13-diol；6,13-Diphenyl-6,13-dihydro-pentacen-6,13-diol；6,13-diphenylpentacene-6,13-diol
• CAS: 76727-14-5
• 化学式: C₃₄H₂₄O₂
• 分子量: 464.563
• InChiKey: YDZDBOFWUAHORO-UHFFFAOYSA-N

物化性质

• 沸点：
  694.8±50.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6,13-diphenyl-6,13-dihydropentacene-6,13-diol 在 二硫化碳 、 air 、 溶剂黄146 、 potassium iodide 作用下， 生成 epidioxy-6,13 diphenyl-6,13 dihydro-6,13 pentacene
  参考文献：
  名称：

  Action of Grignard Reagents on Certain Pentacenequinones, 6,13-Diphenylpentacene

  摘要：

  DOI：

  10.1021/ja01258a005
• 作为产物：
  描述：

  epidioxy-6,13 diphenyl-6,13 dihydro-6,13 pentacene 以86%的产率得到
  参考文献：
  名称：

  SPARFEL D.; GOBERT F.; RIGAUDY J., TETRAHEDRON, 1980, 36, NO 15, 2225-2235

  摘要：

  DOI：

文献信息

• Substituent Effects in Pentacenes: Gaining Control over HOMO−LUMO Gaps and Photooxidative Resistances
  作者：Irvinder Kaur、Wenling Jia、Ryan P. Kopreski、Selvapraba Selvarasah、Mehmet R. Dokmeci、Chandrani Pramanik、Nicol E. McGruer、Glen P. Miller

  DOI：10.1021/ja804515y

  日期：2008.12.3

  A combined experimental and computational study of a series of substituted pentacenes including halogenated, phenylated, silylethynylated and thiolated derivatives is presented. Experimental studies include the synthesis and characterization of six new and six known pentacene derivatives and a kinetic study of each derivative under identical photooxidative conditions. Structures, HOMO-LUMO energies

  介绍了一系列取代并五苯的实验和计算研究，包括卤化、苯基化、甲硅烷基乙炔化和硫醇化衍生物。实验研究包括六种新的和六种已知的并五苯衍生物的合成和表征，以及每种衍生物在相同光氧化条件下的动力学研究。在 B3LYP/6-311+G**//PM3 水平计算结构、HOMO-LUMO 能量和相关间隙，同时通过实验测量光学和电化学 HOMO-LUMO 间隙。综合结果首次提供了对大量并五苯衍生物作为取代基函数的 HOMO-LUMO 间隙和抗光氧化性的定量评估。每个并五苯衍生物的持久性受到空间电阻和电子效应的组合以及每个取代基的位置的影响。与普遍看法相反，甲硅烷基乙炔基取代的并五苯（如 TIPS-并五苯）具有小的 HOMO-LUMO 间隙，但不是光氧化条件下寿命最长的物种。在 2,3,9,10 位具有氯取代基和在 6,13 位具有邻烷基苯基取代基的并五苯衍生物比 TIPS-并五苯寿命更长。在所有研究的衍生物中
• Exciton Isolation in Cross-Pentacene Architecture
  作者：M. P. Lijina、Alfy Benny、Remya Ramakrishnan、Nanditha G. Nair、Mahesh Hariharan

  DOI：10.1021/jacs.0c06016

  日期：2020.10.14

  substituted pentacene derivatives. Partitioned influence of aryl and pentacene fragments on interchromophoric noncovalent interactions and photophysical properties respectively resulted in the emergence of pentacene centric Kasha's ideal null exciton, providing novel in-sights towards the design strategies for cross-stacked chromophoric assemblies. Identifying Greek cross-stacked architecture mediated

  空聚集体是难以捉摸的、新兴的分子组装类，被归类为光谱非耦合分子。正交堆叠的发色团阵列被认为是无效聚合的突出架构。在此，我们揭示了 6,13-​​双芳基取代并五苯衍生物的一系列结晶希腊十字 (+) 组装中的零激子特征。量子化学计算表明协同垂直取向和显着的发色团间分离实现了可忽略的长程库仑和短程电荷转移介导的空聚集体中的耦合。并五苯二聚体的希腊十字 (+) 取向表现出选择性更高的电子转移耦合和接近零的空穴转移耦合，从而有助于降低电荷转移介导的耦合，即使在较短的发色团间距离下也是如此。对并五苯二聚体激子态性质的其他研究证明，任何偏离 90° 交叉堆叠方向的偏差都会导致离域 Frenkel/混合 Frenkel-CT 特征的出现，以及随之而来的空激子/单体样特性的丧失。即使在短程耦合状态下激子隔离的保留也保证了垂直交叉堆叠并五苯系统中零激子特性的普遍性。通过观察 6,13-​​双芳基取代并五苯衍生
• Photooxidation and reproduction of pentacene derivatives substituted by aromatic groups
  作者：Katsuhiko Ono、Hiroaki Totani、Takao Hiei、Akihiro Yoshino、Katsuhiro Saito、Katsuya Eguchi、Masaaki Tomura、Jun-ichi Nishida、Yoshiro Yamashita

  DOI：10.1016/j.tet.2007.07.021

  日期：2007.9

  Pentacene derivatives substituted by aromatic groups at the 6,13-positions were prepared and investigated for their electronic properties and the photoaddition reaction with oxygen. The pentacene derivatives substituted by 2-thienyl and phenyl groups reacted with oxygen in solution under light and afforded their endoperoxides. These first-order kinetic constants were evaluated to be 1.5×10−3 s−1 and

  制备了在6,13位被芳基取代的并五苯衍生物，并研究了它们的电子性质以及与氧的光加成反应。被2-噻吩基和苯基取代的并五苯衍生物在光照下与溶液中的氧反应，得到其内过氧化物。这些一阶动力学常数经评估为1.5×10 -3  s -1和2.7×10 -3  s -1。具有五氟苯基的并五苯衍生物在溶液中相对稳定。具有2-噻吩基的内过氧化物的热解和光解在溶液中得到并五苯衍生物，其产率分别为30％和44％。另外，研究了内过氧化物薄膜的紫外线照射（254 nm），这表明并五苯衍生物的复制。
• Organization of Acenes with a Cruciform Assembly Motif
  作者：Qian Miao、Xiaoliu Chi、Shengxiong Xiao、Roswitha Zeis、Michael Lefenfeld、Theo Siegrist、Michael L. Steigerwald、Colin Nuckolls

  DOI：10.1021/ja0570786

  日期：2006.2.1

  This study explores the assembly in the crystalline state of a class of pentacenes that are substituted along their long edges with aromatic rings forming rigid, cruciform molecules. The crystals were grown from the gas phase, and their structures were compared with DFT-optimized geometries. Both crystallographic and computed structures show that a planar acene core is the exception rather than the rule. In the assembly of these molecules, the phenyl groups block the herringbone motif and further guide the arrangement of the acene core into higher order structures. The packing for the phenyl-substituted derivatives is dictated by close contacts between the C-H's of the pendant aromatic rings and the carbons at the fusions in the acene backbone. Using thiciphene substituents instead of phenyls creates cofacially stacked acenes. In thin films, the thiophene-substituted derivative forms devices with good electrical properties: relatively high mobility, high ON/OFF ratios, and low threshold voltage for device activation. An unusual result is obtained for the decaphenyl pentacene when devices are fabricated on its crystalline surface. Although its acene cores are well isolated from each other, this material still exhibits good electrical properties.
• Etienne; Beauvois, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1954, vol. 239, p. 64
  作者：Etienne、Beauvois

  DOI：——

  日期：——