1,4-diethynyl-2,5-di(4'-tert-butylphenyl)benzene | 608534-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-diethynyl-2,5-di(4'-tert-butylphenyl)benzene
• 英文别名: 4,4''-di-tert-butyl-2',5'-diethynyl-1,1':4',1''-terphenyl；2',5'-bis(bromoethynyl) 4,4"-di‑tert‑butyl‑1,1':4',1"-terphenyl；1,4-Bis(4-tert-butylphenyl)-2,5-diethynylbenzene
• CAS: 608534-48-1
• 化学式: C₃₀H₃₀
• 分子量: 390.568
• InChiKey: XVDJBOBLMJJKPC-UHFFFAOYSA-N

物化性质

• 沸点：
  521.9±50.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-diethynyl-2,5-di(4'-tert-butylphenyl)benzene 在 sodium periodate 、 rhodium(III) chloride hydrate 、 platinum(II) chloride 作用下， 以 氯仿 、 水 、 甲苯 、 乙腈 为溶剂， 生成 3,10-di-tert-butyldibenzo[a,h]anthracene-5,6,12,13-tetraone
  参考文献：
  名称：

  用于合成硝化多环芳烃的二苯并蒽醌化合物。

  摘要：

  报道了合成两个二苯并[ a，h ]蒽-5,6,12,13-二醌构件的直接方法。为了展示其有用性，已合成了一系列的二苯并[ a，h ]蒽氮化衍生物，它们显示出不同的光电，氧化还原和电荷传输性质，说明了它们作为有机半导体的潜力。

  DOI：

  10.1021/acs.orglett.0c01536
• 作为产物：
  描述：

  1,4-dibromo-2,5-di(4'-tert-butylphenyl)benzene 在 哌啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 1,4-diethynyl-2,5-di(4'-tert-butylphenyl)benzene
  参考文献：
  名称：

  From Branched Polyphenylenes to Graphite Ribbons

  摘要：

  This article presents the synthesis of graphitic nanoribbons (similar to1 nm wide), containing extended conjugated all-benzenoid segments. These were obtained by intramolecular oxidative cyclode-hydrogenation of soluble branched polyphenylenes 6, which were prepared by repetitive Diels-Alder cycloaddition of 1,4-bis(2,4,5-triphenylcyclopentadienone-3-yl)benzene (1) and diethynylterphenyl (5) in good yield. While insolubility of the obtained graphite ribbons 7 precluded standard spectroscopic structure elucidation, the electronic and vibrational properties were probed by solid-state UV-vis, Raman, and infrared spectroscopy. A wide and unstructured absorption band covering the visible range of the electronic spectrum (lambda(max) similar to 800 nm) is observed, confirming the highly extended conjugated framework. The structure proof of the ribbon-type polymer is supported by the inclusion of appropriate model compounds. The profile of the visible Raman spectrum of the material is similar to that of a discrete polycyclic aromatic hydrocarbon (PAH) C(222)H(42), characterized by two strong bands (at 1603 and 1322 cm(-1)), corresponding to the G and D bands of graphite. The obtained graphite ribbons are not linear but rather contain "kinks" due to the structural design of the polyphenylene precursor. High-resolution transmission electron microscopy (HRTEM) images of the graphite ribbons 7 disclose two different domains: one is an ordered graphite layer structure with a layer distance of ca. 3.8 Angstrom, and one is disordered due to the existence of "kinks" in the obtained polymers and/or random stacking of graphite ribbons. Attempts to make linear analogues are so far unsuccessful, emphasizing the critical importance of the geometry of the polyphenylene scaffold to successful oxidative cyclodehydrogenation.

  DOI：

  10.1021/ma0257752

文献信息

• Electron-transporting PAHs with dual perylenediimides: syntheses and semiconductive characterizations
  作者：Zhuoran Zhang、Ting Lei、Qifan Yan、Jian Pei、Dahui Zhao

  DOI：10.1039/c3cc40704g

  日期：——

  An effective method was developed to prepare triphenyleno[1,2,3,4-ghi]perylenediimide derivatives, via ICl-induced annulation, dehalogenation, followed by photocyclization. A perylenediimide (PDI) dimer featuring a terphenyl bisethynylene linker was thereby transformed into a benzo[k]tetraphene fused with two benzoperylenediimides. These PDI derivatives exhibited electron mobility up to 0.079 cm2 V−1 s−1 in solution-processed thin film transistors.

  通过 ICl 诱导的环化、脱卤和光环化，开发出了一种制备三苯基烯并[1,2,3,4-ghi]过二亚胺衍生物的有效方法。以三联苯二乙炔连接体为特征的过乙二亚胺（PDI）二聚体由此转化为与两个苯并过乙二亚胺融合的苯并[k]四烯。这些 PDI 衍生物在溶液加工的薄膜晶体管中显示出高达 0.079 cm2 V-1 s-1 的电子迁移率。