9-[bromo-(phenyl)methylene]-9H-fluorene | 33735-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9-[bromo-(phenyl)methylene]-9H-fluorene
• 英文别名: 9-(bromo(phenyl)methylene)-9H-fluorene；9-[Bromo(phenyl)methylene]-9H-fluorene；9-(α-bromo-benzylidene)-fluorene；9-(α-Brom-benzyliden)-fluoren；9-[bromo(phenyl)methylidene]fluorene
• CAS: 33735-95-4
• 化学式: C₂₀H₁₃Br
• mdl: MFCD01211162
• 分子量: 333.227
• InChiKey: GMFPCFIMQWGRRD-UHFFFAOYSA-N

物化性质

• 沸点：
  435.2±24.0 °C(Predicted)
• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  9-[bromo-(phenyl)methylene]-9H-fluorene 在 sodium hydroxide 、 potassium methanolate 、 potassium hexacyanoferrate(III) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Bis-diphenylene-1.3-phenyl-2 allyle-Radikal
  参考文献：
  名称：

  �ber substituierte Bis-biphenylen-allyl-Radikale

  摘要：

  DOI：

  10.1007/bf00909246
• 作为产物：
  描述：

  9-苄亚甲基芴 在 溴 作用下， 以 乙酸乙酯 为溶剂， 生成 9-[bromo-(phenyl)methylene]-9H-fluorene
  参考文献：
  名称：

  Von der basenkatalysiertenRingöffnungvon 2 H -Azirinen zu einerα-AlkylierungsmethodevonprimärenAminen †

  摘要：

  从2 H-嗪的碱催化开环到伯胺的α-烷基化方法

  DOI：

  10.1002/hlca.19810640509

文献信息

• ORGANIC ELECTROLUMINESCENT DEVICE BASED ON NEUTRAL FREE-RADICAL ELECTROLUMINESCENT MATERIAL
  申请人：JILIN UNIVERSITY

  公开号：US20160099415A1

  公开（公告）日：2016-04-07

  Disclosed is an organic electroluminescent device, wherein the light-emitting layer is composed of a non-doped neutral free-radical electroluminescent material or a neutral free-radical electroluminescent material doped in a matrix material. The luminescence of the device is from the photons emitted from the transition of doublet electrons in the outer molecular orbit of the neutral free-radical electroluminescent material from an excited state to the ground state; since there is no limitation on spin-forbidden, the upper limit of the internal quantum efficiency of the device is 100%. The neutral free-radical electroluminescent material used in the device is 1,3-bis(diphenylene)-2-phenylallyl free radicals and derivatives thereof; tri(2,4,6-trichlorophenyl)methyl free radicals and derivatives thereof; (3,5-dichloro-4-pyridyl)bis(2,4,6-trichlorophenyl)methyl free radicals and derivatives thereof; (2,4,6-trichloro-5-pyrimidinyl)bis(2,4,6-trichlorophenyl)methyl free radicals and derivatives thereof.

  本发明涉及一种有机电致发光器件，其中发光层由非掺杂的中性自由基电致发光材料或者在基质材料中掺杂的中性自由基电致发光材料组成。该器件的发光是来自于中性自由基电致发光材料外层分子轨道中双电子跃迁所发射的光子；由于没有自旋禁阻限制，该器件的内部量子效率的上限为100%。该器件中使用的中性自由基电致发光材料包括1,3-双(二苯基)-2-苯基丙烯基自由基及其衍生物；三(2,4,6-三氯苯基)甲基自由基及其衍生物；(3,5-二氯-4-吡啶基)双(2,4,6-三氯苯基)甲基自由基及其衍生物；(2,4,6-三氯-5-嘧啶基)双(2,4,6-三氯苯基)甲基自由基及其衍生物。
• Synthesis of Multisubstituted Triphenylenes and Phenanthrenes by Cascade Reaction of <i>o</i>-Iodobiphenyls or (<i>Z</i>)-β-Halostyrenes with <i>o</i>-Bromobenzyl Alcohols through Two Sequential C–C Bond Formations Catalyzed by a Palladium Complex
  作者：Masayuki Iwasaki、Yasuhiro Araki、Shohei Iino、Yasushi Nishihara

  DOI：10.1021/acs.joc.5b01693

  日期：2015.9.18

  bearing both nucleophilic and electrophilic substituents, for the facile synthesis of polycyclic aromatic hydrocarbons. A palladium/electron-deficient phosphine catalyst efficiently coupled o-iodobiphenyls or (Z)-β-halostyrenes with o-bromobenzyl alcohols to afford triphenylenes and phenanthrenes, respectively. The present cascade reaction proceeded through deacetonative cross-coupling and sequential intramolecular

  邻溴苄醇已被开发为一种新型的带有亲核和亲电取代基的环化试剂，可轻松合成多环芳烃。钯/电子不足的膦催化剂有效地将邻碘联苯或（Z）-β-卤代苯乙烯与邻溴苄醇偶联，分别制得三亚苯基和菲。目前的级联反应是通过去乙酰化交叉偶联和顺序分子内环化进行的。大量实验数据表明，反应机理涉及1,4-钯迁移的平衡。
• Photolysis of the vinyl bromide 9-(α-bromobenzylidene)fluorene in methanol. Effect of wavelength of irradiation, sodium methoxide and oxygen
  作者：J.M. Verbeek、J. Cornelisse、G. Lodder

  DOI：10.1016/s0040-4020(01)88173-4

  日期：1986.1

  A quantitative study of the photosolvolysis of 9-(α-bromobenzylidene)fluorene (1) in methanol reveals that the wavelength of irradiation, the presence of sodium methoxide and the presence of oxygen strongly influence the product distribution and the quantum yields of the reaction.

  定量研究9-（α-溴亚苄基）芴（1）在甲醇中的光溶剂分解结果表明，辐照的波长，甲醇钠的存在和氧的存在强烈影响产物的分布和反应的量子产率。
• Rhodium(I)‐α‐Phenylvinylfluorenyl Complexes: Synthesis, Characterization, and Evaluation as Initiators in the Stereospecific Polymerization of Phenylacetylene
  作者：Nicholas Sheng Loong Tan、Peter V. Simpson、Gareth L. Nealon、Alexandre N. Sobolev、Paolo Raiteri、Massimiliano Massi、Mark I. Ogden、Andrew B. Lowe

  DOI：10.1002/ejic.201801411

  日期：2019.2.7

  The synthesis, characterization and use, as initiators for phenylacetylene polymerizations, of three new rhodium(I)‐vinyl complexes containing fluorenyl functionality with fluorine‐functionalized phosphine ligands is described. Rh(nbd)(CPh=CFlu)P(4‐FC6H4)3, Rh(nbd)(CPh=CFlu)P(4‐CF3C6H4)3, and Rh(nbd)(CPh=CFlu)P[3,5‐(CF3)2C6H3]3 (nbd: 2,5‐norbornadiene; Flu: fluorenyl) were prepared and isolated as

  描述了三种新的含芴基官能团和氟官能化膦配体的铑（I）-乙烯基配合物的合成，表征和用作苯乙炔聚合的引发剂。Rh（nbd）（CPh = CFlu）P（4-FC 6 H 4）3，Rh（nbd）（CPh = CFlu）P（4-CF 3 C 6 H 4）3和Rh（nbd）（CPh = CFlu）P [3,5-（CF 3）2 C 6 H 3 ] 3（nbd：2,5-降冰片二烯;流感：芴基）制备并分离为离散的橙色化合物，易于重结晶，得到X射线质量的晶体。所有配合物的特征都是1 H，31 P，19 F，103 Rh NMR光谱和2D 31 P- 103 Rh / 31 P- 103 Rh 103Rh}异核多量子相关性（HMQC）实验，元素分析和单晶X射线分析。该复合物作为活性苯乙炔的配合插入在聚合引发剂，与起始效率跨越范围13-56％，并且得到低分散度（的聚苯乙炔d =中号瓦特/中号Ñ）具有高顺式transoidal立体规整性。
• Spectroscopic and electrical characterization of α,γ-bisdiphenylene-β-phenylallyl radical as an organic semiconductor
  作者：Yasunori Matsui、Minoru Shigemori、Toshiyuki Endo、Takuya Ogaki、Eisuke Ohta、Kazuhiko Mizuno、Hiroyoshi Naito、Hiroshi Ikeda

  DOI：10.1007/s11164-018-3282-7

  日期：2018.8

  The semiconductor properties of the earliest known stable radical, α,γ-bisdiphenylene-β-phenylallyl radical (Koelsch radical, 1•) were assessed using spectroscopic and electrical techniques. This radical undergoes reversible redox processes, and it has low redox potentials. In addition, 1• possesses long wavelength absorption bands, owing to the existence of a singly-occupied molecular orbital whose

  使用光谱学和电学技术评估了已知的最早的稳定自由基，即α，γ-双二亚苯基-β-苯基烯丙基（Koelsch自由基，1 •）的半导体性质。该自由基经历可逆的氧化还原过程，并且氧化还原电位低。此外，1 •具有长波长吸收带，由于一个单独占领分子轨道，其能级谎言那些HOMO和LUMO之间的存在。1 •的旋涂薄膜显示光电流和6.3×10 -7  cm 2  V -1  s -1的电子迁移率 在一个预制的有机场效应晶体管上。