9,9-didecylfluorene | 123864-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9,9-didecylfluorene
• 英文别名: 9,9-didecyl-9H-fluorene；9,9-di-n-decyl-9H-fluorene
• CAS: 123864-01-7
• 化学式: C₃₃H₅₀
• 分子量: 446.76
• InChiKey: GNBBEOGRQXANFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  546.1±20.0 °C(predicted)
• 密度：
  0.919±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 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-didecylfluorene 在 palladium 10% on activated carbon 、 氢气 、 硝酸 、 sodium hydride 、 碳酸氢钠 、 溶剂黄146 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 异丙醇 、 mineral oil 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 2.0h， 生成 tert-butyl 2,2'-(9,9-didecyl-9H-fluorene-2,7-diyl)bis(tert-butoxycarbonylazanediyl)diacetate
  参考文献：
  名称：

  Fulleropyrrolidine End-Capped Molecular Wires for Molecular Electronics—Synthesis, Spectroscopic, Electrochemical, and Theoretical Characterization

  摘要：

  In continuation of previous studies showing promising metal molecule contact properties a variety of C-60 end-capped "molecular wires" for molecular electronics were prepared by variants of the Prato 1,3-dipolar cycloaddition reaction. Either benzene or fluorene was chosen as the central wire, and synthetic protocols for derivatives terminated with one or two fullero[c]pyrrolidine "electrode anchoring" groups were developed. An aryl-substituted aziridine could in some cases be employed directly as the azomethine ylide precursor for the Prato reaction without the need of having an electron-withdrawing ester group present. The effect of extending the pi-system of the central wire from 1,4-phenylenediamine to 2,7-fluorenediamine was investigated by absorption, fluorescence, and electrochemical methods. The central wire and the Co-60 end-groups were found not to electronically communicate in the ground state. However, the fluorescence of C60 was quenched by charge transfer from the wire to C-60. Quantum chemical calculations predict and explain the collapse of coherent electronic transmission through one of the fulleropyrrolidine-terminated molecular wires.

  DOI：

  10.1021/jo102066x
• 作为产物：
  描述：

  芴 、 癸基溴 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 120.17h， 以64%的产率得到9,9-didecylfluorene
  参考文献：
  名称：

  Improving the compatibility of fullerene acceptors with fluorene-containing donor-polymers in organic photovoltaic devices

  摘要：

  含氟荧光烃的PCBM类化合物已被合成，并与聚氟荧光共聚物PF10TBT在有机光伏器件中进行了测试，与以PCBM作为受体材料的器件相比，开路电压提高了约130毫伏。

  DOI：

  10.1039/c0cc01347a

文献信息

• Electroactive and luminescent polymers: new fluorene-heterocycle-based hybrids
  作者：Barbara Tsuie、Jerry L. Reddinger、Gregory A. Sotzing、Jadwiga Soloducho、Alan R. Katritzky、John R. Reynolds

  DOI：10.1039/a903374b

  日期：——

  The synthesis, characterization, and electrochromic properties of copolymers derived from 9,9-dialkyl-2,7-dibromofluorene (18a, alkyl=C 10 H 21 ; 24, alkyl=Et) and pyrrole, thiophene, 3,4-ethylenedioxythiophene, and furan are described. Two synthetic routes to 9,9-diethyl-2,7-bis(pyrrol-2-yl)fluorene (30) afford product in 30% and 20% yields, respectively. Monomer 30 undergoes electropolymerizationto yield electroactive polymer films. The lowest monomer oxidation potential (E p,m =0.4 V vs. Ag/Ag + ) is found in tetraethylammonium tosylate (TEATOS)-CH 3 CN, but film formation is slow. Spectroelectrochemical analysis of poly(30) reveals a band gap at 2.4 eV and upon polymer oxidation, two low energy absorptions peaking at 1.2 and 2.2 eV appear. This phenomenon is attributed to formation of bipolaron bands between the valence and conduction bands. Soluble fluorene-heterocycle polymers 34a-d have been synthesized by the Stille coupling reaction of 18a and 2,5-bis(trimethylstannyl)thiophene (21a), 5,5′-bis(trimethylstannyl)-2,2′-bithiophene (21b), 2,5-bis(trimethylstannyl)-3,4-ethylenedioxythiophene (21c), and 2,5-bis(trimethylstannyl)furan (22), respectively, in high yields. The NMR spectra are consistent with the proposed structures of the polymers 34a-d, and no evidence of ring opening of the furyl unit in 34d is seen in the NMR and IR spectra. The molecular weights of 34a-d are in the range of 8000 g mol –1 with polydispersity indices (PDI) of 2. Polymers 34a-c have band gaps measured at 2.4 eV, while polymer 34d has its gap at 2.6 eV. Polymers 34a-c undergo solution doping with SbCl 5 to form new low energy bipolaron bands at the expense of the absorption in the UV-VIS. However, polymer 34d does not oxidatively dope with SbCl 5 .

  描述了从9,9-二烷基-2,7-二溴芴（18a，烷基=C10H21；24，烷基=Et）和吡咯、噻吩、3,4-亚乙基二氧噻吩以及呋喃衍生的共聚物的合成、表征和电致变色性质。两条合成9,9-二乙基-2,7-双（吡咯-2-基）芴（30）的路线分别获得了30%和20%的产率。单体30经电化学聚合生成电活性聚合物薄膜。最低单体氧化电位（Ep,m=0.4 V vs. Ag/Ag+）在四乙基铵对甲苯磺酸盐（TEATOS）-CH3CN中观察到，但薄膜形成缓慢。光谱电化学分析发现聚30的带隙为2.4 eV，聚合物氧化后出现两个低能量吸收峰，峰值为1.2 eV和2.2 eV，这一现象归因于价带和导带之间双极化子带的形成。通过Stille偶联反应，18a分别与2,5-双（三甲基锡基）噻吩（21a）、5,5′-双（三甲基锡基）-2,2′-双噻吩（21b）、2,5-双（三甲基锡基）-3,4-亚乙基二氧噻吩（21c）和2,5-双（三甲基锡基）呋喃（22）反应，合成了可溶性芴-杂环聚合物34a-d，产率较高。NMR光谱与所提出的聚合物34a-d的结构一致，NMR和IR光谱中未观察到34d中呋喃单元的开环证据。34a-d的分子量在8000 g mol–1范围内，多分散性指数（PDI）为2。聚合物34a-c的带隙测得为2.4 eV，而聚合物34d的带隙为2.6 eV。聚合物34a-c通过溶液掺杂SbCl5形成新的低能量双极化子带，以牺牲紫外-可见光吸收为代价。然而，聚合物34d不能通过SbCl5进行氧化掺杂。
• Improving the compatibility of fullerene acceptors with fluorene-containing donor-polymers in organic photovoltaic devices
  作者：Jan-Carlos Kuhlmann、Paul de Bruyn、Ricardo K. M. Bouwer、Auke Meetsma、Paul W. M. Blom、Jan C. Hummelen

  DOI：10.1039/c0cc01347a

  日期：——

  Fluorene-containing PCBM analogs have been synthesized and tested with a polyfluorene copolymer, PF10TBT, in organic photovoltaic devices resulting in an increase of ∼130 mV in the open circuit voltage compared to devices with PCBM as acceptor material.

  含氟荧光烃的PCBM类化合物已被合成，并与聚氟荧光共聚物PF10TBT在有机光伏器件中进行了测试，与以PCBM作为受体材料的器件相比，开路电压提高了约130毫伏。
• Characterization of novel sulfonium photoacid generators and their microwave-assisted synthesis
  作者：Ciceron O. Yanez、Carolina D. Andrade、Kevin D. Belfield

  DOI：10.1039/b815831b

  日期：——

  Microwave-assisted synthesis of triarylsulfonium salt photoacid generators (PAGs) afforded reaction times 90 to 420 times faster than conventional thermal conditions, with photoacid quantum yields of new sulfonium PAGs ranging from 0.01 to 0.4.

  微波辅助合成三芳基锍盐光酸发生器（PAGs）的反应时间比传统热条件快 90 至 420 倍，新型锍 PAGs 的光量子产率为 0.01 至 0.4。
• Fulleropyrrolidine End-Capped Molecular Wires for Molecular Electronics—Synthesis, Spectroscopic, Electrochemical, and Theoretical Characterization
  作者：Jakob Kryger Sørensen、Jeppe Fock、Anders Holmen Pedersen、Asger B. Petersen、Karsten Jennum、Klaus Bechgaard、Kristine Kilså、Victor Geskin、Jérôme Cornil、Thomas Bjørnholm、Mogens Brøndsted Nielsen

  DOI：10.1021/jo102066x

  日期：2011.1.7

  In continuation of previous studies showing promising metal molecule contact properties a variety of C-60 end-capped "molecular wires" for molecular electronics were prepared by variants of the Prato 1,3-dipolar cycloaddition reaction. Either benzene or fluorene was chosen as the central wire, and synthetic protocols for derivatives terminated with one or two fullero[c]pyrrolidine "electrode anchoring" groups were developed. An aryl-substituted aziridine could in some cases be employed directly as the azomethine ylide precursor for the Prato reaction without the need of having an electron-withdrawing ester group present. The effect of extending the pi-system of the central wire from 1,4-phenylenediamine to 2,7-fluorenediamine was investigated by absorption, fluorescence, and electrochemical methods. The central wire and the Co-60 end-groups were found not to electronically communicate in the ground state. However, the fluorescence of C60 was quenched by charge transfer from the wire to C-60. Quantum chemical calculations predict and explain the collapse of coherent electronic transmission through one of the fulleropyrrolidine-terminated molecular wires.