5-bromo-5'-carbodecaoxy-2,2'-bithiophene | 875767-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-bromo-5'-carbodecaoxy-2,2'-bithiophene
• 英文别名: decyl 5'-bromo-2,2'-bithiophene-5-carboxylate；8-bromo-5'-decyloxycarbonyl-[2,2']-bithiophene；Decyl 5-(5-bromothiophen-2-yl)thiophene-2-carboxylate；decyl 5-(5-bromothiophen-2-yl)thiophene-2-carboxylate
• CAS: 875767-29-6
• 化学式: C₁₉H₂₅BrO₂S₂
• 分子量: 429.442
• InChiKey: VTFGGWWSXBYGRB-UHFFFAOYSA-N

物化性质

• 熔点：
  47-48.5 °C
• 沸点：
  487.3±45.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-5'-carbodecaoxy-2,2'-bithiophene 、 5,5-双三甲基硅烷基-2,2'-联噻吩 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以90%的产率得到bis-decyl 2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-sexithiophene-5,5'''''-dicarboxylate
  参考文献：
  名称：

  Synthesis and field-effect properties of α,ω -disubstituted sexithiophenes bearing polar groups

  摘要：

  本文描述了在α,ω-末端位置带有酰胺或酯基团的六噻吩的合成及其在固态下的表征。研究了官能团对有机场效应晶体管(FET)器件中迁移率和开/关比的影响。带有酯官能团并通过乙烯间隔基与六噻吩核心分离的寡聚物，其空穴场效应迁移率高达0.012 cm² V⁻¹ s⁻¹，这是迄今为止报道的使用极性基团修饰的六噻吩的有机场效应晶体管中最高的之一。

  DOI：

  10.1039/b515583e
• 作为产物：
  描述：

  癸醇 、 5'-bromo-2,2'-bithiophene-5-carbonyl chloride 在 吡啶 作用下， 以 甲苯 为溶剂， 以98%的产率得到5-bromo-5'-carbodecaoxy-2,2'-bithiophene
  参考文献：
  名称：

  Synthesis and field-effect properties of α,ω -disubstituted sexithiophenes bearing polar groups

  摘要：

  本文描述了在α,ω-末端位置带有酰胺或酯基团的六噻吩的合成及其在固态下的表征。研究了官能团对有机场效应晶体管(FET)器件中迁移率和开/关比的影响。带有酯官能团并通过乙烯间隔基与六噻吩核心分离的寡聚物，其空穴场效应迁移率高达0.012 cm² V⁻¹ s⁻¹，这是迄今为止报道的使用极性基团修饰的六噻吩的有机场效应晶体管中最高的之一。

  DOI：

  10.1039/b515583e

文献信息

• Novel bifluorene based conjugated systems: synthesis and properties
  作者：Roberto Grisorio、Antonio Dell'Aquila、Giuseppe Romanazzi、Gian Paolo Suranna、Piero Mastrorilli、Pynalisa Cosma、Domenico Acierno、Eugenio Amendola、Giuseppe Ciccarella、Cosimo Francesco Nobile

  DOI：10.1016/j.tet.2005.10.010

  日期：2006.1

  A series of novel bifluorene based systems was synthesised by a convergent approach by means of a Suzu'ki cross-coupling between 7,7'-bis-(4,4,5,5-tetramethyl-[1,3,2]dioxaboi-olan-2-yl)-9,9,9,9'-tetraoctyl-2,2'-bifluorene and suitable aryl-bromides. All the oligomers have been characterized by H-1, C-13 NMR, Fr-IR, UV-vis, PL spectroscopy and mass analyses. In particular, it has been demonstrated that the presence of strong electron donor (amines) or withdrawing (carboxylic esters) groups causes a bathochromic shift of the optical properties with respect to those of unsubstituted molecules. The effects of these functional groups on the HOMO-LUMO energy levels were investigated by cyclic voltammetry. Remarkably, the LUMO energy level of 7,7'-bis-[5-carbodecaoxy-2,2'-bithiophen-5-yl]-9,9,9',9'-tetraoctyl-2,2'-bifluorene (-3.07 eV) is strongly influenced by the presence of the ester functional group. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of bifluorene-based molecular materials: effect of C-9 spirocyclohexane functionalization and end-group tailoring
  作者：Roberto Grisorio、Claudia Piliego、Pinalysa Cosma、Paola Fini、Piero Mastrorilli、Giuseppe Gigli、Gian Paolo Suranna、Cosimo Francesco Nobile

  DOI：10.1016/j.tet.2008.06.098

  日期：2008.9

  The preparation and properties of the first spirocyclohexane-functionalized bifluorene-based mono-dispersed molecular materials is described. The obtained compounds were characterized by (1)H NMR, (13)C[(1)H] NMR, IR, DSC, UV-vis and photoluminescence both in solution and in the solid state. The molecules show emissions ranging from the blue to the blue-green region, and higher glass transition temperatures and spectral stability with respect to the analogous compounds containing 9,9,9',9'-tetrahexyl-[2,2']-bifluorene core. The materials were used as active layers in electroluminescent devices with ITO/PEDOT-PSS/SB1-4/Ca/Al and ITO/PEDOT-PSS/SB1-4/BCP/Ca/Al configurations. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and field-effect properties of α,ω -disubstituted sexithiophenes bearing polar groups
  作者：Antonio Dell'Aquila、Piero Mastrorilli、Cosimo Francesco Nobile、Giuseppe Romanazzi、Gian Paolo Suranna、Luisa Torsi、Maria Cristina Tanese、Domenico Acierno、Eugenio Amendola、Piero Morales

  DOI：10.1039/b515583e

  日期：——

  The synthesis of sexithiophenes bearing amide or ester groups in the α,ω-terminal positions is described, along with their characterization in the solid state. The influence of the functional group on mobilities and on/off ratios of the organic FET devices was investigated. The oligomer bearing the ester functional group separated from the sexithiophene core by an ethylene spacer showed a hole field-effect mobility as high as 0.012 cm2 V−1 s−1, which is among the highest reported so far for organic FETs using sexithiophenes modified with polar groups.

  本文描述了在α,ω-末端位置带有酰胺或酯基团的六噻吩的合成及其在固态下的表征。研究了官能团对有机场效应晶体管(FET)器件中迁移率和开/关比的影响。带有酯官能团并通过乙烯间隔基与六噻吩核心分离的寡聚物，其空穴场效应迁移率高达0.012 cm² V⁻¹ s⁻¹，这是迄今为止报道的使用极性基团修饰的六噻吩的有机场效应晶体管中最高的之一。