9,9,9',9'-tetrahexyl-9H,9'H-2,2'-bifluorene | 264925-44-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9,9,9',9'-tetrahexyl-9H,9'H-2,2'-bifluorene
• 英文别名: 2,2'-(9,9-Dihexyl)bifluorene；2-(9,9-dihexylfluoren-2-yl)-9,9-dihexylfluorene
• CAS: 264925-44-2
• 化学式: C₅₀H₆₆
• 分子量: 667.074
• InChiKey: FTCUMWZMKRXDTD-UHFFFAOYSA-N

物化性质

• 沸点：
  755.6±55.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  19.4
• 重原子数：
  50
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  9,9,9',9'-tetrahexyl-9H,9'H-2,2'-bifluorene 在 四(三苯基膦)钯 、 水 、 氢溴酸 、 potassium carbonate 、 sodium hydrogensulfite 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 40.0h， 生成 2-(9,9-Dihexylfluoren-2-yl)-7-[7-(9,9-dihexylfluoren-2-yl)-9,9-dihexylfluoren-2-yl]-9,9-dihexylfluorene
  参考文献：
  名称：

  Delocalization of Positive and Negative Charge Carriers on Oligo- and Poly-fluorenes Studied by Low-Temperature Matrix Isolation Technique

  摘要：

  通过逐步的铃木偶联反应合成了具有明确链长（n = 1–5）的寡氟烯，作为聚氟烯中共轭段的基础。寡氟烯的阳离子和阴离子自由基（n > 2）表现出明显的三条红外吸收，归因于氟烯结构单元之间的SOMO态与骨架中的价态（HOMO）或导电态（LUMO）之间的跃迁。红外带的跃迁能量在单位数范围内从1.2 eV线性下降到0.55 eV，而一维激子跃迁能量在n > 5时显示出明显的饱和。这意味着沿氟烯链的多余电子或空穴的去局部化程度在比中性激子更大的单位数时会达到饱和。

  DOI：

  10.1246/cl.2004.1290
• 作为产物：
  描述：

  9,9-二己基-2-溴芴 在 nickel dichloride 2,2'-联吡啶 、 三苯基膦 、 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 48.0h， 以70%的产率得到9,9,9',9'-tetrahexyl-9H,9'H-2,2'-bifluorene
  参考文献：
  名称：

  Monodisperse fluorene oligomers exhibiting strong dipolar coupling interactions

  摘要：

  通过逐步Suzuki和Yamamoto偶联反应，制备了定义明确的芴寡聚物（n = 1到6），其吸收和光致发光性质表明芴基团之间存在非常大的偶极耦合相互作用。

  DOI：

  10.1039/b201414a

文献信息

• Monodisperse fluorene oligomers exhibiting strong dipolar coupling interactions
  作者：Rémi Anémian、Jean-Christophe Mulatier、Chantal Andraud、Olivier Stéphan、Jean-Claude Vial

  DOI：10.1039/b201414a

  日期：2002.7.11

  Well-defined fluorene oligomers (n = 1 to 6) were prepared step by step using Suzuki and Yamamoto couplings, while absorption and photoluminescence properties evidenced very large dipolar coupling interactions between fluorene moieties.

  通过逐步Suzuki和Yamamoto偶联反应，制备了定义明确的芴寡聚物（n = 1到6），其吸收和光致发光性质表明芴基团之间存在非常大的偶极耦合相互作用。
• Photophysical, electrochemical, and crystallographic investigation of conjugated fluoreno azomethines and their precursors
  作者：Sergio Andrés Pérez Guarìn、Stéphane Dufresne、Derek Tsang、Assa Sylla、W. G. Skene

  DOI：10.1039/b618098a

  日期：——

  The photophysical investigation of amino- and aldehyde-substituted fluorenes revealed that these compounds are not only highly fluorescent, but dissipation of their singlet excited energy occurs by a combination of nonradiative means involving intersystem crossing (ISC) and internal conversion (IC). Quantification of the triplet state formed by ISC was possible by laser-flash photolysis (LFP). The efficiency by which this manifold was populated varied between 10 and 40% depending on the fluorene substitution. Condensation of these aldehyde and amine precursors yielded conjugated thiopheno azomethines with robust covalent bonds. Fluorescence of the azomethinefluorene derivatives was reduced relative to their precursors while the degree of IC remained unchanged. Deactivation of the singlet excited state occurred predominately by ISC and the resulting triplet state was rapidly and efficiently quenched by energy transfer by the azomethine linkage. Cyclic voltammetry of the fluoreno azomethines showed both oxidation and reduction processes, and the measured redox potentials and the band-gaps are lower than a bisfluorene analogue. The fluoreno azomethine LUMO energy levels are sufficiently low, making them compatible with common cathodes, therefore eliminating the use of an electron-injection layer.

  氨基和醛基取代的芴类化合物的光物理研究表明，这些化合物不仅高度荧光，而且它们的单重态激发能量通过包括跨系统跃迁（ISC）和内部转换（IC）在内的非辐射方式进行耗散。通过激光闪光光解（LFP）可以定量分析由ISC形成的三重态。该状态的填充效率因芴的取代而异，范围在10%到40%之间。这些醛和胺前驱体的缩合反应产生了具有强健共价键的共轭噻吩亚胺。与其前驱体相比，亚胺-芴衍生物的荧光强度降低，而内部转换的程度保持不变。单重态激发态的消耗主要通过ISC发生，所产生的三重态则通过亚胺链的能量转移迅速且高效地被猝灭。芴亚胺的循环伏安法显示出氧化和还原过程，测得的氧还原电位和带隙均低于双芴类类似物。芴亚胺的LUMO能级足够低，使其与常见的阴极兼容，从而消除了使用电子注入层的需要。
• Synthesis and characterization of N-carbazole end-capped oligofluorenes
  作者：Vinich Promarak、Sayant Saengsuwan、Siriporn Jungsuttiwong、Taweesak Sudyoadsuk、Tinnagon Keawin

  DOI：10.1016/j.tetlet.2006.11.007

  日期：2007.1

  A series of N-carbazole end-capped oligofluorenes (CFn, n = 1–3) were synthesized. The 9-position of the carbazole moiety was attached to the terminal ends of the oligofluorene cores using an Ullmann coupling reaction. These molecules exhibit red shifts in absorption and photoluminescence spectra with respect to the number of fluorene units and excellent electrochemical reversibility. They were found

   合成了一系列N-咔唑封端的低聚芴（CF n，n = 1-3）。使用Ullmann偶联反应，将咔唑部分的9位连接至低聚芴核的末端。这些分子相对于芴单元的数量在吸收光谱和光致发光光谱中表现出红移，并具有出色的电化学可逆性。发现它们是用于有机发光二极管（OLED）的潜在的蓝色发光或空穴传输材料。
• Molecular Weight Engineering in High‐Performance Ambipolar Emissive Mesopolymers
  作者：Xiaofei Guo、Yihan Zhang、Yongxu Hu、Jiaxin Yang、Yang Li、Zhenjie Ni、Huanli Dong、Wenping Hu

  DOI：10.1002/anie.202105036

  日期：2021.6.25

  Herein, three low-molecular-weight mesopolymers with thienopyrroledione–benzothiadiazole repeating units (meso-TBTF) were obtained. The mesopolymers show strong solid-state emission and high ambipolar carrier mobility. The molecular weights of meso-TBTF can be tuned by polymerization temperature. The mesopolymers have photoluminescence quantum yields (PLQY) of about 50 % in solution and 10 % in solid state

  具有高溶解度、无结构缺陷且批次间差异可忽略不计的介聚物为有机光电子学开辟了一条新途径。有机发光晶体管结合了有机发光二极管和有机场效应晶体管的功能。然而，在一种共轭聚合物中，电荷传输能力和发光强度是矛盾的。在此，获得了三种具有噻吩并吡咯二酮-苯并噻二唑重复单元（meso-TBTF）的低分子量内聚体。内聚体显示出强烈的固态发射和高双极性载流子迁移率。内消旋 TBTF 的分子量可以通过聚合温度进行调节。内聚体的光致发光量子产率 (PLQY) 在溶液中约为 50%，在固态时约为 10%。
• Mechanochemical synthesis of biphenyl-derived organic fluorescent materials <i>via</i> solvent-free and ligand-free oxidative homocoupling reactions
  作者：Zefeng Li、Caihang Zhang、Yingxuan Zheng、Ping Deng、Yan Yu

  DOI：10.1039/d4nj00886c

  日期：2024.4.22

  ball-milling method have been reported. These reactions allow simple, fast, and efficient synthesis of a series of biphenyl-derived organic fluorescent materials in modest and good yields without the use of ligands in air. The new organic fluorescent material N-[4-(4-phenyl[4-(triphenylvinyl)phenyl]amino}phenyl)-phenyl]-N-[4-(triphenylvinyl)phenyl]aniline (B6) shows typical aggregation-induced emission

  已经报道了使用无溶剂和无配体球磨方法的钯催化芳基硼酸的氧化自偶联反应。这些反应可以简单、快速、有效地合成一系列联苯衍生的有机荧光材料，且产率适中且良好，无需在空气中使用配体。新型有机荧光材料N -[4-(4-苯基[4-(三苯基乙烯基)苯基]氨基}苯基)-苯基] -N- [4-(三苯基乙烯基)苯基]苯胺( B6 )表现出典型的聚集诱导发射特征和可逆机械力响应荧光特性。