7,9-di(thiophen-2-yl)-8H-cyclopenta[a]acenaphthylen-8-one | 1070195-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7,9-di(thiophen-2-yl)-8H-cyclopenta[a]acenaphthylen-8-one
• 英文别名: 7,9-dithiophen-2-ylcyclopenta[a]acenaphthylen-8-one
• CAS: 1070195-35-5
• 化学式: C₂₃H₁₂OS₂
• 分子量: 368.48
• InChiKey: JGGUUNAKTDAUSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7,9-di(thiophen-2-yl)-8H-cyclopenta[a]acenaphthylen-8-one 在 溴 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 以95%的产率得到
  参考文献：
  名称：

  Visible−Near Infrared Absorbing Dithienylcyclopentadienone−Thiophene Copolymers for Organic Thin-Film Transistors

  摘要：

  Structural design, synthesis, and characterization of a series of organic semiconductors consisting exclusively of dithienylcyclopentadienone subunits within a polythiophene backbone are described as the first example for organic electronic devices. The donor (thiophene)-alt-acceptor (cyclopentadienone) copolymers exhibit a substantial p-carrier mobility in OFET but an unexpected noncorrelation between absorption and photoconductivity.

  DOI：

  10.1021/ja806784e
• 作为产物：
  描述：

  1,3-二(噻吩-2-基)丙烷-2-酮 、 苊醌 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以72%的产率得到7,9-di(thiophen-2-yl)-8H-cyclopenta[a]acenaphthylen-8-one
  参考文献：
  名称：

  异苯并呋喃/环戊二烯酮与四硫富瓦烯的狄尔斯-阿尔德反应：萘，荧蒽和芴酮衍生物的制备

  摘要：

  1,3-二芳基苯并[ c ]呋喃/环戊二烯酮与TTF的Diels-Alder反应，然后由三氟乙酸介导裂解所生成的加合物，从而形成各自的1,4-二芳基取代的萘，荧蒽和芴酮。还报道了代表性的二芳基取代的烃的光物理性质。

  DOI：

  10.1021/acs.orglett.7b03686

文献信息

• Diels–Alder Reaction of Isobenzofurans/Cyclopentadienones with Tetrathiafulvalene: Preparation of Naphthalene, Fluoranthene, and Fluorenone Derivatives
  作者：Jayachandran Karunakaran、Arasambattu K. Mohanakrishnan

  DOI：10.1021/acs.orglett.7b03686

  日期：2018.2.16

  Diels–Alder reaction of 1,3-diarylbenzo[c]furan/cyclopentadienone with TTF followed by triflic acid mediated cleavage of the resulting adducts led to the formation of the respective 1,4-diaryl substituted naphthalenes, fluoranthenes, and fluorenones. The photophysical properties of representative diaryl-substituted hydrocarbons are also reported.

  1,3-二芳基苯并[ c ]呋喃/环戊二烯酮与TTF的Diels-Alder反应，然后由三氟乙酸介导裂解所生成的加合物，从而形成各自的1,4-二芳基取代的萘，荧蒽和芴酮。还报道了代表性的二芳基取代的烃的光物理性质。
• Diels–Alder reaction of tetraarylcyclopentadienones with benzo[<i>b</i>]thiophene <i>S</i>,<i>S</i>-dioxides: an unprecedented de-oxygenation <i>vs.</i> sulfur dioxide extrusion
  作者：Palani Manikandan、Jayachandran Karunakaran、Elumalai Varathan、Georg Schreckenbach、Arasambattu K Mohanakrishnan

  DOI：10.1039/d0cc05842d

  日期：——

  benzo[b]thiophene dioxides in xylenes at reflux led to the formation of tetra aryl-substituted dibenzothiophene as well as penta aryl-substituted benzene analogues depending on the influence of aryl substituents present on cyclopentadienones. The intermediate dihydrodibenzothiophene-dioxides underwent aromatization either through de-oxygenation or extrusion of sulfur dioxide to furnish substituted dibenzothiophenes

  四芳基环戊二烯酮与二甲苯中的苯并[ b ]噻吩二氧化物在回流下的Diels-Alder反应导致四芳基取代的二苯并噻吩以及五芳基取代的苯类似物的形成，具体取决于芳基取代基对环戊二烯的影响。中间体二氢二苯并噻吩二氧化物通过脱氧或挤出二氧化硫进行芳构化，以提供取代的二苯并噻吩或苯。
• A Donor–Acceptor–Donor Structured Organic Conductor with S···S Chalcogen Bonding
  作者：Monalisa Bai、Sajesh P. Thomas、Ranjith Kottokkaran、Susanta K. Nayak、Praveen C. Ramamurthy、T. N. Guru Row

  DOI：10.1021/cg401069y

  日期：2014.2.5

  A novel thiophene derivative 7,9-di(thiophen-2-yl)-8H-cyclopenta[a]acenaphthylen-8-one (DTCPA) is shown to exhibit high electrical conductivity (1.97 x 10(-2) +/- 0.0018 S/cm at RT) in the crystalline state. The material shows two orders of increase in conductivity from normal solid to single crystalline state. The crystal structure has S center dot center dot center dot S chalcogen bonding, C-H center dot center dot center dot O hydrogen bonding, and pi center dot center dot center dot pi stacking as the major intermolecular interactions. The nature and strength of the S center dot center dot center dot S interactions in this structure have been evaluated by theoretical charge density analysis, and its contribution to the crystal packing quantified by Hirshfeld surface analysis. Further, thermal and morphological characterizations have been carried out, and the second harmonic generation (SHG) efficiency has been measured using the Kurtz-Perry method.
• Visible−Near Infrared Absorbing Dithienylcyclopentadienone−Thiophene Copolymers for Organic Thin-Film Transistors
  作者：Changduk Yang、Shinuk Cho、Ryan C. Chiechi、Wesley Walker、Nelson E. Coates、Daniel Moses、Alan J. Heeger、Fred Wudl

  DOI：10.1021/ja806784e

  日期：2008.12.10

  Structural design, synthesis, and characterization of a series of organic semiconductors consisting exclusively of dithienylcyclopentadienone subunits within a polythiophene backbone are described as the first example for organic electronic devices. The donor (thiophene)-alt-acceptor (cyclopentadienone) copolymers exhibit a substantial p-carrier mobility in OFET but an unexpected noncorrelation between absorption and photoconductivity.
• Importance of the donor unit on fluoranthene for selective detection of nitro aromatic explosives
  作者：Kasthuri Selvaraj、Praveen B. Managutti、Sharmarke Mohamed、Satyanarayana Talam、Venkatramaiah Nutalapati

  DOI：10.1016/j.jphotochem.2022.114215

  日期：2022.12

  photophysical properties of M1 and T1 were explored in solution, solid-state and their AIEE phenomenon was studied in THF/water systems. Both the compounds show strong sky-blue emission at 453 nm (M1) and 460 nm (T1). The fluorescence lifetime and quantum yields are varied significantly in the aggregated form. The emission enhancement ascribed due to restricted intramolecular rotation (RIR) of thiophene/phenyl

  在这项工作中，合成了两种聚合诱导发射增强 (AIEE) 材料，包括侧翼为荧蒽的苯基 ( M1 ) 和噻吩 ( T1 ) 单元。我们报告了一种新的M1堆积多晶相，晶格中的分子相互作用通过C H···π (2.882 Å) 相互作用得以稳定。单晶X射线衍射（SXRD）研究表明，荧蒽上苯基/噻吩单元的高扭转角赋予晶格中弱的π-π分子间相互作用。M1和T1的光物理性质在溶液、固态中进行了探索，并在 THF/水系统中研究了它们的 AIEE 现象。这两种化合物在 453 nm ( M1 ) 和 460 nm ( T1 )都显示出强烈的天蓝色发射。聚合形式的荧光寿命和量子产率变化很大。由于噻吩/苯基与处于聚集状态的中心π-共轭荧蒽的受限分子内旋转（RIR）而导致的发射增强。通过改变四氢呋喃/水的比例，表面形态的明显变化、光物理性质和能级的变化为其提供了对不同硝基芳烃进行痕量检测的潜力。两种材料都显示出对三硝基苯酚