3,6-dimethoxyfluorene | 96617-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3,6-dimethoxyfluorene
• 英文别名: 2,7-Dimethoxy-fluoren；3,6-Dimethoxy-9H-fluorene
• CAS: 96617-41-3
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: QIPUWRQXLQLWDC-UHFFFAOYSA-N

物化性质

• 沸点：
  369.7±35.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-dimethoxyfluorene 在 正丁基锂 、 四甲基乙二胺 、 溴 、 三氯化铁 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 25.5h， 生成 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dimethoxy-9,9-dihexylfluorene
  参考文献：
  名称：

  Optical and Electrical Properties of π-Conjugated Polymers Based on Electron-Rich 3,6-Dimethoxy-9,9-dihexylfluorene Unit

  摘要：

  A new family of pi-conjugated polymers has been developed using 3,6-dimethoxy-9,9-dihexylfluorene as an electron-rich unit. These electroactive and photoactive polymers have been prepared from nickel(0)-mediated coupling or by palladium-catalyzed Suzuki coupling. These new 3,6-dimethoxy-9,9-dihexylfluorene-based copolymers have demonstrated emission spanning the entire visible spectrum. Moreover, all of these polymers show reversible electroactivity upon reduction and oxidation, and as expected, the presence of methoxy groups onto the fluorene moiety increases the ionization potential of the resulting copolymers by about 0.2 eV when compared with some 9,9-dihexylfluorene-based copolymers. The reduction of the energy barrier for the injection of holes in related polymeric light-emitting devices should contribute to the enhancement of their performances.

  DOI：

  10.1021/ma035064j
• 作为产物：
  描述：

  3,6-二甲氧基-9H-芴-9-酮 在 四氯化钛 、 dimethylamine borane 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到3,6-dimethoxyfluorene
  参考文献：
  名称：

  Optical and Electrical Properties of π-Conjugated Polymers Based on Electron-Rich 3,6-Dimethoxy-9,9-dihexylfluorene Unit

  摘要：

  A new family of pi-conjugated polymers has been developed using 3,6-dimethoxy-9,9-dihexylfluorene as an electron-rich unit. These electroactive and photoactive polymers have been prepared from nickel(0)-mediated coupling or by palladium-catalyzed Suzuki coupling. These new 3,6-dimethoxy-9,9-dihexylfluorene-based copolymers have demonstrated emission spanning the entire visible spectrum. Moreover, all of these polymers show reversible electroactivity upon reduction and oxidation, and as expected, the presence of methoxy groups onto the fluorene moiety increases the ionization potential of the resulting copolymers by about 0.2 eV when compared with some 9,9-dihexylfluorene-based copolymers. The reduction of the energy barrier for the injection of holes in related polymeric light-emitting devices should contribute to the enhancement of their performances.

  DOI：

  10.1021/ma035064j

文献信息

• Chemical and physical properties of 3,6-dimethoxyfluorenylidene: substituent effects making the ground state a singlet carbene
  作者：Carl Chuang、Stephen C. Lapin、Alan K. Schrock、Gary B. Schuster

  DOI：10.1021/ja00300a027

  日期：1985.7

  Preparation du carbene par irradiation du diazo-9 dimethoxy-3,6 fluorene. Etude RPE. Reactions du carbene avec le methanol et le cyclohexane

  制备杜卡宾帕辐照杜重氮-9 二甲氧基-3,6芴。练习曲 RPE。反应杜卡宾 avec le 甲醇 et le 环己烷
• 3,6-Fluoren[5]arenes: synthesis, structure and complexation with fullerenes C₆₀ and C₇₀
  作者：Jia-Qi Wang、Ying Han、Chuan-Feng Chen

  DOI：10.1039/d1cc00916h

  日期：——

  in good yields by one-step reaction. The 3,6-fluoren[5]arenes had symmetric pentagon structures with big and rich-electron cavities, which made them form 1 : 1 complexes with fullerenes C60 and C70. The association constants of the complexes were all greater than 105 M−1.

  一种新型的大环芳烃，3,6-芴[5]芳烃，可通过一步反应方便地以高收率合成。3,6-芴[5]芳烃具有对称的五边形结构，具有大而富电子的空穴，这使它们与富勒烯C 60和C 70形成1：1的配合物。配合物的缔合常数均大于10 5 M -1。
• Transition Metal Complex, Process For Producing Said Transition Metal Complex, Substituent-Carrying Fluorene Compound, Process For Producing Said Fluorene Compound, Catalyst Component For Olefin Polymerization, Catalyst For Olefin Polymerization, and Process For Producing Olefin Polymer
  申请人：Senda Taichi

  公开号：US20080161514A1

  公开（公告）日：2008-07-03

  A transition metal complex represented by the general formula [1]; a catalyst component for olefin polymerization comprising said transition metal complex; a catalyst for olefin polymerization using said transition metal complex as a catalyst component for olefin polymerization; a process for producing an olefin polymer comprising the step of polymerizing an olefin in the presence of said catalyst for olefin polymerization; a substituent-carrying fluorene compound; a process for producing said substituent-carrying fluorene compound; and a process for producing said transition metal complex using said substituent-carrying fluorene compound: wherein M is the group 4 transition metal atom in the periodic table of elements; A is the group 16 atom therein; J is the group 14 atom therein; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X 1 and X 2 are independently of one another (1) a substituent selected from the group consisting of (1-1) an alkyl group having 1 to 20 carbon atoms, which may be substituted by a halogen atom, (1-2) an aralkyl group having 7 to 20 carbon atoms, which may be substituted by a halogen atom, (1-3) an aryl group having 6 to 20 carbon atoms, which may be substituted by a halogen atom, (1-4) a substituent-carrying silyl group having 1 to 20 carbon atoms, which substituent is a hydrocarbyl group, and said hydrocarbyl group may be substituted by a halogen atom, (1-5) a disubstituent-carrying amino group having 2 to 20 carbon atoms, which substituent is a hydrocarbyl group, and said hydrocarbyl group may be substituted by a halogen atom, (1-6) an alkoxy group having 1 to 20 carbon atoms, which may be substituted by a halogen atom, (1-7) an aralkyloxy group having 7 to 20 carbon atoms, which may be substituted by a halogen atom, and (1-8) an aryloxy group having 6 to 20 carbon atoms, which may be substituted by a halogen atom, (2) a halogen atom or (3) a hydrogen atom; R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 may be linked to each other, respectively, to form respective rings; R 5 and R 6 may be linked to each other to form a ring; R 7 , R 8 , R 9 and R 10 are independently of one another (1) a substituent selected from the group consisting of (1-1) an alkyl group having 1 to 20 carbon atoms, which may be substituted by a halogen atom, (1-2) an aralkyl group having 7 to 20 carbon atoms, which may be substituted by a halogen atom, (1-3) an aryl group having 6 to 20 carbon atoms, which may be substituted by a halogen atom, (1-4) a substituent-carrying silyl group having 1 to 20 carbon atoms, which substituent is a hydrocarbyl group, and said hydrocarbyl group may be substituted by a halogen atom, (1-5) a disubstituent-carrying amino group having 2 to 20 carbon atoms, which substituent is a hydrocarbyl group, and said hydrocarbyl group may be substituted by a halogen atom, (1-6) an alkoxy group having 1 to 20 carbon atoms, which may be substituted by a halogen atom, (1-7) an aralkyloxy group having 7 to 20 carbon atoms, which may be substituted by a halogen atom, and (1-8) an aryloxy group having 6 to 20 carbon atoms, which may be substituted by a halogen atom, (2) a halogen atom or (3) a hydrogen atom; at least two of R 7 , R 8 , R 9 and R 10 are the substituent selected from the above-mentioned group or a halogen atom; R 7 and R 8 may be linked to each other to form a ring; and R 9 and R 10 may be linked to each other to form a ring.

  一种以通式[1]表示的过渡金属配合物；一种包括该过渡金属配合物的烯烃聚合催化剂组分；一种使用该过渡金属配合物作为烯烃聚合催化剂组分的烯烃聚合催化剂；一种在该烯烃聚合催化剂存在下聚合烯烃的方法；一种携带取代基的芴化合物；一种制备该携带取代基的芴化合物的方法；以及一种使用该携带取代基的芴化合物制备该过渡金属配合物的方法：其中，M是元素周期表中的第4族过渡金属原子；A是其中的第16族原子；J是其中的第14族原子；R1、R2、R3、R4、R5、R6、X1和X2各自独立地是（1）选自以下组中的取代基：（1-1）具有1至20个碳原子的烷基取代基，其可以被卤素原子取代，（1-2）具有7至20个碳原子的芳基烷基取代基，其可以被卤素原子取代，（1-3）具有6至20个碳原子的芳基取代基，其可以被卤素原子取代，（1-4）携带取代基的具有1至20个碳原子的硅烷基，其取代基是烃基，且该烃基可以被卤素原子取代，（1-5）携带二个取代基的具有2至20个碳原子的氨基取代基，其取代基是烃基，且该烃基可以被卤素原子取代，（1-6）具有1至20个碳原子的烷氧基，其可以被卤素原子取代，（1-7）具有7至20个碳原子的芳基烷氧基，其可以被卤素原子取代，以及（1-8）具有6至20个碳原子的芳氧基，其可以被卤素原子取代，（2）卤素原子或（3）氢原子；R1和R2、R2和R3以及R3和R4可以分别相互连接以形成相应的环；R5和R6可以连接以形成环；R7、R8、R9和R10各自独立地是（1）选自上述组中的取代基：（1-1）具有1至20个碳原子的烷基取代基，其可以被卤素原子取代，（1-2）具有7至20个碳原子的芳基烷基取代基，其可以被卤素原子取代，（1-3）具有6至20个碳原子的芳基取代基，其可以被卤素原子取代，（1-4）携带取代基的具有1至20个碳原子的硅烷基，其取代基是烃基，且该烃基可以被卤素原子取代，（1-5）携带二个取代基的具有2至20个碳原子的氨基取代基，其取代基是烃基，且该烃基可以被卤素原子取代，（1-6）具有1至20个碳原子的烷氧基，其可以被卤素原子取代，（1-7）具有7至20个碳原子的芳基烷氧基，其可以被卤素原子取代，以及（1-8）具有6至20个碳原子的芳氧基，其可以被卤素原子取代，（2）卤素原子或（3）氢原子；R7、R8、R9和R10中至少有两个是上述组中的取代基或卤素原子；R7和R8可以连接以形成环；R9和R10可以连接以形成环。
• CHUANG, C.;LAPIN, S. C.;SCHROCK, A. K.;SCHUSTER, G. B., J. AMER. CHEM. SOC., 1985, 107, N 14, 4238-4243
  作者：CHUANG, C.、LAPIN, S. C.、SCHROCK, A. K.、SCHUSTER, G. B.

  DOI：——

  日期：——
• Skeletal Editing of Dibenzolactones to Fluorenes via Ni- or Pd-Catalyzed Decarboxylation
  作者：Liang-Yu Chen、Junqi Li

  DOI：10.1021/acs.joc.3c00700

  日期：2023.7.21