2,5-bis(9-hydroxyfluoren-9-yl)thiophene | 136970-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,5-bis(9-hydroxyfluoren-9-yl)thiophene
• 英文别名: 9-[5-(9-Hydroxyfluoren-9-yl)thiophen-2-yl]fluoren-9-ol
• CAS: 136970-39-3
• 化学式: C₃₀H₂₀O₂S
• 分子量: 444.554
• InChiKey: NZVDVULBGFNNGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-bis(9-hydroxyfluoren-9-yl)thiophene 在 氢碘酸 、 乙酸酐 、 溶剂黄146 作用下， 生成 2,5-bis(9-fluorenyl)thiophene
  参考文献：
  名称：

  Thermal and photochemical formation of quinonoid derivatives of condensed polythiophenes and their spectral properties

  摘要：

  Quinonoid derivatives of linearly condensed thiophenes have been prepared from the precusor diols thermally as well as photochemically and their spectral characteristics are demonstrated.

  DOI：

  10.1016/s0040-4039(00)92172-5
• 作为产物：
  描述：

  9-芴酮 、 2,5-dilithiothiophene 以 四氢呋喃 为溶剂， 生成 2,5-bis(9-hydroxyfluoren-9-yl)thiophene
  参考文献：
  名称：

  2,5-双（二芳基亚甲基）-2,5-二氢噻吩及其呋喃，硒烯和N-甲基吡咯类似物的制备

  摘要：

  一系列的2,5-双（二芳基亚甲基）-2,5-二氢噻吩及其呋喃，硒醚和N-甲基吡咯类似物可分三步合成，从2,5-二锂化的五元杂芳族化合物和2当量的二芳基开始酮或2,5-二氮酰基五元杂芳族化合物和2当量的芳基锂。

  DOI：

  10.1016/s0040-4039(00)92158-0

文献信息

• Solid-State Solvolysis of Thiophene-Substituted Trityl-Type Alcohols:  Nucleophilic Substitution Induced by Gas−Solid Contact
  作者：Motoko Tanaka、Naoki Tanifuji、Shigeru Hatada、Keiji Kobayashi

  DOI：10.1021/jo001291x

  日期：2001.2.1

  suggested by the ESR spectrum. The mechanism involving the collapse of the radical cation to generate a proton, which acts as a catalyst to afford the carbocation, was deduced based on the electrochemical oxidation of the substrate in solution. The propagation of the substitution reaction in the solid state has been shown for the carbocation upon contact with methanol vapor. The crystalline inclusion

  已经研究了通过气固接触的亲核取代反应。当将9-噻吩并噻吩芴-9-ol衍生物与二氯二氰基醌（DDQ）共研磨，然后暴露于甲醇蒸气中时，以15-70％的产率获得相应的9-甲氧基芴。在整个过程中，固态保持不变。ESR光谱表明，通过底物醇与DDQ之间的电荷转移相互作用，在共研磨的固体中生成了自由基阳离子。基于溶液中底物的电化学氧化，推导了涉及自由基阳离子分解产生质子的机理，该质子充当提供碳正离子的催化剂。对于与甲醇蒸气接触的碳正离子，已经显示出固态的取代反应的传播。将以甲醇为客体的9-噻吩并噻吩基芴-9-醇衍生物的结晶包合物暴露于HCl气体中。该气固反应还导致形成保持固态的相应甲氧基化合物。通过这项工作，得出了固态共研磨的新结果。
• Fluorescent Molecular Complexes of 9-Hydroxyfluoren-9-yl Substituted Thiophene and Thienothiophenes with 1,2,4,5-Tetracyanobenzene:Crystalline Complexation of Bulky and Conformationally Mobile Molecules
  作者：Naoto Hayashi、Keiji Kobayashi

  DOI：10.1080/10587259608039373

  日期：1996.2

  Bis(9-hydroxyfluoren-9-yl)-substituted thiophene (1), thieno-[3,2-b]thiophene (2), and thieno[2,3-b]thiophene (3) were recrystallized with 1,2,4,5-tetracyanobenzene (TCNB) from CH2Cl2 to afford crystalline complexes (1)(2)(TCNB), (2)(TCNB)(CH2Cl2), and (3)(TCNB)(CH2Cl2), respectively. These crystals are yellow and fluorescent in the solid state. X-ray analyses of (1)(2)(TCNB) and (3)(TCNB)(CH2Cl2) revealed that the fluorenyl moieties and the TCNB ring are arranged in a face-to-face manner. The coloring and fluorescent properties are ascribed to a weak charge-transfer (CT) interaction, which is brought about by lattice controlled packing rather than intrinsic CT interactions. The nature of the fluorescence is discussed on the basis of the crystal structure and the lifetime of the emission.
• Preparation of 2,5-bis(diarylmethylene)-2,5-dihydrothiophenes and their furan, selenophene, and N-methylpyrrole analogs
  作者：Akihiko Ishii、Yasuaki Horikawa、Ikuo Takaki、Jun Shibata、Juzo Nakayama、Masamatsu Hoshino

  DOI：10.1016/s0040-4039(00)92158-0

  日期：1991.1

  A series of 2,5-bis(diarylmethylene)-2,5-dihydrothiophenes and their furan, selenophene, and N-methylpyrrole analogs were synthesized in three steps either starting from 2,5-dilithiated five-membered heteroaromatics and 2 equiv of diaryl ketones or from 2,5-diaroyl five-membered heteroaromatics and 2 equiv of aryllithiums.

  一系列的2,5-双（二芳基亚甲基）-2,5-二氢噻吩及其呋喃，硒醚和N-甲基吡咯类似物可分三步合成，从2,5-二锂化的五元杂芳族化合物和2当量的二芳基开始酮或2,5-二氮酰基五元杂芳族化合物和2当量的芳基锂。
• Thermal and photochemical formation of quinonoid derivatives of condensed polythiophenes and their spectral properties
  作者：Yasuhiro Mazaki、Shinobu Murata、Keiji Kobayashi

  DOI：10.1016/s0040-4039(00)92172-5

  日期：1991.1

  Quinonoid derivatives of linearly condensed thiophenes have been prepared from the precusor diols thermally as well as photochemically and their spectral characteristics are demonstrated.