2,7-dibromo-9,9-di[2-(2-tetrahydropyranyloxy)ethyl]fluorene | 807618-43-5

• 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: 2,7-dibromo-9,9-di[2-(2-tetrahydropyranyloxy)ethyl]fluorene
• 英文别名: 2-{2-[2,7-dibromo-9-(2-perhydro-2H-pyran-2-yloxyethyl)fluoren-9-yl]ethoxy}perhydro-2H-pyran；2,2'-{[(2,7-dibromo-9H-fluorene-9,9-diyl)bis(ethane-2,1-diyl)]bis(oxy)}bis(tetrahydro-2H-pyran)；9,9-bis[2'-(tetrahydropyranyloxy)ethyl]-2,7-dibromo-9H-fluorene；9-bis[2-(perhydro-2H-pyran-2-yloxy)ethyl]-2,7-dibromofluoren；2-[2-[2,7-Dibromo-9-[2-(oxan-2-yloxy)ethyl]fluoren-9-yl]ethoxy]oxane；2-[2-[2,7-dibromo-9-[2-(oxan-2-yloxy)ethyl]fluoren-9-yl]ethoxy]oxane
• CAS: 807618-43-5
• 化学式: C₂₇H₃₂Br₂O₄
• 分子量: 580.357
• InChiKey: WNWMNQMEIWRHDT-UHFFFAOYSA-N

物化性质

• 熔点：
  95-97 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  636.4±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,7-dibromo-9,9-di[2-(2-tetrahydropyranyloxy)ethyl]fluorene 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以87.1%的产率得到2-[2,7-二溴-9-(2-羟基乙基)芴-9-基]乙醇
  参考文献：
  名称：

  通过热诱导（复古）-Diels-环戊二烯基取代基的Alder交联来调节聚芴发射体的溶解度

  摘要：

  对于具有成本效益的有机电子设备，通过基于溶液的工艺连续沉积有源层是一个关键优势。我们报告了一种合成方法，该方法能够降低双（环戊二烯基）取代的聚芴作为有机发光二极管（OLED）中的发光层的溶解度。热诱导的逆Diels-Alder反应释放出游离的环戊二烯作为“保护基”和未决的环戊二烯基单元，这些单元通过[4 + 2]环加成反应冷却后可将聚合物链交联。通过烷基，烷氧基或酯键，可以将活化温度调节在180–250°C的范围内。最终，大环自我保护的双（环戊二烯）部分避免了活化过程中挥发性环戊二烯的挤出。通过吸收光谱法和白光扫描干涉法检查交联后的发光层的耐溶剂性。研究了增溶过程对溶液加工的OLED性能的影响。

  DOI：

  10.1021/acs.chemmater.8b01703
• 作为产物：
  描述：

  芴 在 sodium hydroxide 、 四乙基溴化铵 、 溴 、 三氯化铁 、 对苯二酚 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 2,7-dibromo-9,9-di[2-(2-tetrahydropyranyloxy)ethyl]fluorene
  参考文献：
  名称：

  Synthesis, Solid-Phase Reaction, Optical Properties, and Patterning of Luminescent Polyfluorenes

  摘要：

  The homopolymer of 9,9-di(2-(2-tetrahydropyranyloxy)ethyl)fluorene and copolymers based on 9,9-dihexylfluorene, thiophene, and 3-(2-(2-tetrahydropyranyloxy)ethyl)thiophene repeat units were obtained as patternable blue, green, and blue-green color luminescent polymers. Thermolytic and acid-catalyzed removal of the bulky tetrahydropyran (THP) group from thin solid films of the polymers was investigated. The acid-catalyzed deprotection can be carried out at a significantly lower temperature than thermolytic deprotection in the absence of acid. The effect of the acid-catalyzed deprotection of these polyfluorenes (PFs) on the photoluminescent properties was studied. Prior to deprotection, the polyfluorenes show good optical properties and high emission intensity both in solution and in the solid state. After deprotection, their optical properties were retained and their quantum yields of photoluminescence remained high, but their solubility was reduced due to the presence of hydroxyl groups. The decrease in solubility allows for their spatially controlled deposition using chemically amplified soft lithography.

  DOI：

  10.1021/ma0488562

文献信息

• Solubility Modulation of Polyfluorene Emitters by Thermally Induced (Retro)-Diels–Alder Cross-Linking of Cyclopentadienyl Substituents
  作者：Lukas Ahrens、Stefan Schlisske、Karl-Philipp Strunk、Felix Hinkel、Christian Melzer、Uwe H. F. Bunz、Uli Lemmer、Gerardo Hernandez-Sosa、Daniel Jänsch、Jan Freudenberg、Klaus Müllen

  DOI：10.1021/acs.chemmater.8b01703

  日期：2018.6.26

  devices, the consecutive deposition of active layers by solution-based processes is a key benefit. We report a synthetic approach enabling solubility reduction of bis(cyclopentadienyl)-substituted polyfluorenes as emissive layers in organic light-emitting diodes (OLEDs). Thermally induced retro-Diels–Alder reaction liberates free cyclopentadiene as “protecting group” and pending cyclopentadienyl units

  对于具有成本效益的有机电子设备，通过基于溶液的工艺连续沉积有源层是一个关键优势。我们报告了一种合成方法，该方法能够降低双（环戊二烯基）取代的聚芴作为有机发光二极管（OLED）中的发光层的溶解度。热诱导的逆Diels-Alder反应释放出游离的环戊二烯作为“保护基”和未决的环戊二烯基单元，这些单元通过[4 + 2]环加成反应冷却后可将聚合物链交联。通过烷基，烷氧基或酯键，可以将活化温度调节在180–250°C的范围内。最终，大环自我保护的双（环戊二烯）部分避免了活化过程中挥发性环戊二烯的挤出。通过吸收光谱法和白光扫描干涉法检查交联后的发光层的耐溶剂性。研究了增溶过程对溶液加工的OLED性能的影响。
• [EN] COMPOUND, RESIN, POLYCARBONATE RESIN, AND OPTICAL MOLDED BODY<br/>[FR] COMPOSÉ, RÉSINE, RÉSINE DE POLYCARBONATE ET CORPS MOULÉ OPTIQUE<br/>[JA] 化合物、樹脂、ポリカーボネート樹脂、および光学成形体
  申请人：MITSUI CHEMICALS INC

  公开号：WO2022025071A1

  公开（公告）日：2022-02-03

  一般式（１）で表される化合物。 （一般式（１）中、Ａｒ１およびＡｒ２は、独立して、 （ＡＡ）から選ばれる基を表し、Ｒ１～Ｒ６は、水素原子、炭化水素基またはヘテロ原子含有炭化水素基を表し、Ａ１～Ａ５およびＢ１～Ｂ５は、水素原子、炭化水素基またはヘテロ原子含有炭化水素基を表し、Ａ１～Ａ５の少なくとも一つは－Ｙ１－Ａｒ３基であり、Ｂ１～Ｂ５の少なくとも一つは－Ｙ２－Ａｒ４基であり、Ｙ１およびＹ２は単結合または連結基を表し、Ａｒ３およびＡｒ４は芳香族基を表し、Ｘ１～Ｘ４は－Ｏ－、－Ｓ－、－ＮＲ'－または－Ｃ（Ｍｅ）２－であり、Ｚ１～Ｚ４は水素原子、炭化水素基またはヘテロ原子含有炭化水素基を表し、Ｒ'は水素原子、炭化水素基またはヘテロ原子含有炭化水素基を表し、ｏおよびｐは１～４の整数を表す）。

  这是一种由一般式（1）表示的化合物。（在一般式（1）中，Ar1和Ar2独立地表示从（AA）中选择的基团，R1-R6表示氢原子，烃基或含杂原子的烃基，A1-A5和B1-B5表示氢原子，烃基或含杂原子的烃基，A1-A5中至少一个是-Y1-Ar3基团，B1-B5中至少一个是-Y2-Ar4基团，Y1和Y2表示单键或连接基团，Ar3和Ar4表示芳香族基，X1-X4表示-O-，-S-，-NR'-或-C（Me）2-，Z1-Z4表示氢原子，烃基或含杂原子的烃基，R'表示氢原子，烃基或含杂原子的烃基，o和p表示1-4的整数）。
• Stabilized Blue Luminescent Polyfluorenes:  Introducing Polyhedral Oligomeric Silsesquioxane
  作者：Jonghee Lee、Hoon-Je Cho、Byung-Jun Jung、Nam Sung Cho、Hong-Ku Shim

  DOI：10.1021/ma0497759

  日期：2004.11.1

  A new POSS (polyhedral oligomeric silsesquioxane)-substituted polyfluorene was synthesized from the nickel-catalyzed Yamamoto coupling reaction. The synthesized polymers could be well characterized by H-1 NMR, FT-IR, and elemental analysis. PL spectra of PFPOSSs on the quartz film showed reduced aggregation/excimer formation because the bulky POSS group prohibited interchain interactions. This effective dilution effect and the high thermal stability of the POSS unit also improved the color stability of PFPOSSs blue emission even after thermal annealing at 150 degreesC. The fluorescence quantum yields (Phi(FL)) of PFPOSSs in both solution and solid state were higher than those of poly(dialkylfluorene)s. Moreover, the ITO/PEDOT-PSS/polymer/Ca/Al LED device using this polymer as emitting layer showed a very stable blue light emission. LED devices of PFPOSSs showed a low turn-on voltage of 3.7-4.4 V, high brightness of 350-1010 cd/m(2), and external efficiencies of 0.11-0.36%.
• WO2006/59884
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis, Solid-Phase Reaction, Optical Properties, and Patterning of Luminescent Polyfluorenes
  作者：Xu Han、Xiwen Chen、George Vamvounis、Steven Holdcroft

  DOI：10.1021/ma0488562

  日期：2005.2.1

  The homopolymer of 9,9-di(2-(2-tetrahydropyranyloxy)ethyl)fluorene and copolymers based on 9,9-dihexylfluorene, thiophene, and 3-(2-(2-tetrahydropyranyloxy)ethyl)thiophene repeat units were obtained as patternable blue, green, and blue-green color luminescent polymers. Thermolytic and acid-catalyzed removal of the bulky tetrahydropyran (THP) group from thin solid films of the polymers was investigated. The acid-catalyzed deprotection can be carried out at a significantly lower temperature than thermolytic deprotection in the absence of acid. The effect of the acid-catalyzed deprotection of these polyfluorenes (PFs) on the photoluminescent properties was studied. Prior to deprotection, the polyfluorenes show good optical properties and high emission intensity both in solution and in the solid state. After deprotection, their optical properties were retained and their quantum yields of photoluminescence remained high, but their solubility was reduced due to the presence of hydroxyl groups. The decrease in solubility allows for their spatially controlled deposition using chemically amplified soft lithography.