5,5-dimethyl-2-(3-octylthien-2-yl)[1,3,2]dioxaborinane | 205104-97-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 5,5-dimethyl-2-(3-octylthien-2-yl)[1,3,2]dioxaborinane
• 英文别名: [1',3'-(2',2'-dimethylpropylene)]-3-octyl-2-thienyl boronate；5,5-Dimethyl-2-(3-octylthiophen-2-yl)-1,3,2-dioxaborinane；5,5-dimethyl-2-(3-octylthiophen-2-yl)-1,3,2-dioxaborinane
• CAS: 205104-97-8
• 化学式: C₁₇H₂₉BO₂S
• 分子量: 308.293
• InChiKey: MOHFBLYEEKXUSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-2-(3-octylthien-2-yl)[1,3,2]dioxaborinane 在 四(三苯基膦)钯 mercury(II) diacetate 、 碘 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 溶剂黄146 为溶剂， 生成 5'''-Chloro-5-iodo-3,4',4'',4'''-tetraoctyl-[2,2';5',2'';5'',2''']quaterthiophene
  参考文献：
  名称：

  1H and13C NMR study of regioregular head-to-tail oligo(octylthiophene)s and poly(octylthiophene)

  摘要：

  The H-1 and C-13 signals of the aromatic region of monodisperse regioregular head-to-tail (HT) oligo(octylthiophene)s ranging from the dimer to the hexamer were assigned in CDCl3 and THF-d(8). The linear dependence of proton chemical shifts on the reciprocal number of thiophenes was demonstrated in both solvents. Weak signals surrounding the main peak in the spectrum of the regioregular HT poly(octylthiophene) were assigned in CDCl3 and THF-d(8) in the light of results obtained for the hexamer. In particular, the end of chain protons of the polymer could be assigned. Spin-lattice relaxation times (T-1) of aromatic protons of the hexamer were measured in CDCl3 and THF-d(8). We observed that T-1 depended on the position of the proton along the main chain. This result was interpreted in terms of molecular motions. Copyright (C) 2001 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1097-458x(200102)39:2<57::aid-mrc799>3.0.co;2-q
• 作为产物：
  描述：

  在 盐酸 作用下， 生成 5,5-dimethyl-2-(3-octylthien-2-yl)[1,3,2]dioxaborinane
  参考文献：
  名称：

  1H and13C NMR study of regioregular head-to-tail oligo(octylthiophene)s and poly(octylthiophene)

  摘要：

  The H-1 and C-13 signals of the aromatic region of monodisperse regioregular head-to-tail (HT) oligo(octylthiophene)s ranging from the dimer to the hexamer were assigned in CDCl3 and THF-d(8). The linear dependence of proton chemical shifts on the reciprocal number of thiophenes was demonstrated in both solvents. Weak signals surrounding the main peak in the spectrum of the regioregular HT poly(octylthiophene) were assigned in CDCl3 and THF-d(8) in the light of results obtained for the hexamer. In particular, the end of chain protons of the polymer could be assigned. Spin-lattice relaxation times (T-1) of aromatic protons of the hexamer were measured in CDCl3 and THF-d(8). We observed that T-1 depended on the position of the proton along the main chain. This result was interpreted in terms of molecular motions. Copyright (C) 2001 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1097-458x(200102)39:2<57::aid-mrc799>3.0.co;2-q

文献信息

• Vers des gels conducteurs calibrés et régioréguliers de poly(octyl-3-thiophène) : préparation du motif élémentaire
  作者：J. Bras、S. Guillerez、B. Pépin-Donat

  DOI：10.1051/jcp:1998237

  日期：1998.6

  Dans le but d'étudier la corrélation propriétés de transport-connecti vité dans des réseaux conducteurs, nous nous proposons de préparer des gels entièrement conjugués parfaitement définis. Notre équipe a déjà obtenu quatre séries de gels statistiques de poly(octylthiophène). Nous voulons maintenant préparer des réseaux homologues dont la longueur et la régiorégularité des bras espaceurs seront contrôlées. Les bras espaceurs de ces gels seront constitués de n (n ≥ 1) sexi(octyl-3-thiophène). La préparation régiosélective du sexithiophène a été optimisée; nous avons approfondi sa caractérisation ainsi que celle des oligomères intermédiaires. Le sexithiophène régiorégulier a été couplé en position 1, 3, 5 d'un cycle benzénique. La molécule ainsi obtenue constitue le motif élémentaire des gels que nous souhaitons préparer.

  为了研究导电网络中传输连接特性的相关性，我们建议制备完美定义的完全共轭凝胶。我们的团队已经获得了四个系列的统计聚辛基噻吩凝胶。我们现在想要准备同源网络，其间隔臂的长度和区域规则性将受到控制。这些凝胶的间隔臂将由 n (n ≥ 1) 六(辛基-3-噻吩) 制成。优化了六噻吩的区域选择性制备；我们加深了它的表征以及中间低聚物的表征。立体规则六噻吩偶联于苯环的1、3、5位。由此获得的分子构成了我们希望制备的凝胶的基本模式。
• Mixed alkylthiophene-based heterocyclic polymers containing oxadiazole units via electrochemical polymerisation: spectroscopic, electrochemical and spectroelectrochemical properties
  作者：Alexander S. FisyukPermanent address: Department、Renaud Demadrille、Claudia Querner、Malgorzata Zagorska、Joël Bleuse、Adam Pron

  DOI：10.1039/b415587d

  日期：——

  Symmetric alkylthiophene-based mixed heterocyclic trimer and pentamer, containing central oxadiazole units, have been prepared. Because of the electron-withdrawing properties of oxadiazole, the trimer cannot be electropolymerised and undergoes an oxidative-type destruction at high potentials. In contrast, the pentamer readily polymerises, giving a short chain polymer. Both trimer and pentamer exhibit strong photoluminescence with a maximum at 399 nm (13% quantum yield) and 467 nm (46% quantum yield), respectively. The polymer resulting from the electropolymerisation of the pentamer is also luminescent with the maximum of the excitation band at 528 nm (33% quantum yield). The polymer can be oxidatively doped as demonstrated by cyclic voltammetry, showing a clear anodic peak at 0.62 V versus Ag/Ag+ and its cathodic counterpart at 0.56 V, associated with the undoping process. The significantly higher potential of the oxidative doping of the prepared mixed heterocyclic polymer, as compared to the poly(alkylthiophene) homopolymer of similar molecular weight, is caused by the presence of the oxadiazole unit, which lowers the electron density in the π-electron system of the oligothiophene subunit and makes its oxidation more difficult. The spectroelectrochemical investigation of the polymer is consistent with its voltammetric behaviour, exhibiting doping-induced bleaching of the band originating from the π-π* transition and simultaneous growth of the bipolaron bands. The observed clear and reversible spectroelectrochemical behaviour makes the developed polymer a promising candidate for applications in electrochromic devices or electrochemical sensors.

  已制备出含中心氧杂二唑单元的对称烷基噻吩基混合杂环三聚体和五聚体。由于氧杂二唑具有吸电子特性，三聚体无法电聚，在高电位下会发生氧化型破坏。相比之下，五聚体易于聚合，形成短链聚合物。三聚体和五聚体均具有强烈的光致发光特性，最大发光波长分别为399 nm（13%量子产额）和467 nm（46%量子产额）。五聚体电聚产生的聚合物也具有发光特性，激发带的最大波长为528 nm（33%量子产额）。循环伏安法表明，该聚合物可发生氧化掺杂，在0.62 V（相对于Ag/Ag+）时出现明显的阳极峰，在0.56 V时出现阴极峰，这与未掺杂过程有关。与分子量相似的聚（烷基噻吩）均聚物相比，所制备的混合杂环聚合物的氧化掺杂电位明显更高，这是由于氧杂二唑单元的存在降低了噻吩亚基π电子系统的电子密度，使其氧化更加困难。聚合物的光谱电化学研究结果与其伏安特性一致，表明掺杂导致π-π*跃迁产生的带出现漂白，双极子带同时增长。所观察到的清晰且可逆的光谱
• Tuning the Electronic Structure of Conjugated Polymers with Fluoroalkyl Substitution:  Alternating Alkyl/Perfluoroalkyl-Substituted Polythiophene
  作者：Ling Li、David M. Collard

  DOI：10.1021/ma048510r

  日期：2005.1.1

  The electronic properties of the conjugated backbone of polythiophene can be tailored by the incorporation of alkyl and perfluoroalkyl substituents. A regioregular copolymer with alternating alkyl and perfluoroalkyl. substituents displays absorption and emission maxima between those of the homopolymers composed of the individual structural units. However, the combination of the alternating electron-rich and electron-poor units, together with a small twisting influence of the perfluoroalkyl groups, provides a material which displays enhanced solution-phase fluorescence and strong solid-state fluorescence which is absent for the wholly alkyl analogue.