2-(n-hexyl)-5-bromothiophene 1,1-dioxide | 211737-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-(n-hexyl)-5-bromothiophene 1,1-dioxide
• 英文别名: 2-Bromo-5-hexylthiophene 1,1-dioxide
• CAS: 211737-29-0
• 化学式: C₁₀H₁₅BrO₂S
• 分子量: 279.198
• InChiKey: ULZFFBCTMZZUJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-hexyl-2,2':5',2''-terthiophene 、 2-(n-hexyl)-5-bromothiophene 1,1-dioxide 在 tetrakis(triphenylarsine)palladium(0) 正丁基锂 、 四甲基乙二胺 、 三丁基氯化锡 作用下， 生成 5,5'''-Dihexyl-[2,2';5',2'';5'',2''']quaterthiophene 1,1-dioxide
  参考文献：
  名称：

  Oligothiophene S,S-Dioxides. Synthesis and Electronic Properties in Relation to the Parent Oligothiophenes

  摘要：

  Oligothiophene S,S-dioxides from dimers to pentamers were obtained in good yields by reaction of mono- and dibrominated thiophene S,S-dioxides with the appropriate thienyl stannanes in the presence of Pd(AsPh3)(4) generated in situ. The reaction rate with brominated thiophene S,S-dioxides is greatly accelerated compared to that employing thienyl bromides to obtain the parent oligothiophenes. HF/6-31G* ab initio calculations on 2,2'-bithiophene and the corresponding mono- and bis-S,S-dioxides show that the functionalization of the thienyl sulfur to the S,S-dioxide does not affect the pi,pi* nature of the frontier orbitals, decreases the energy of the LUMO much more than that of the HOMO, increases the degree of planarity of the molecular skeleton, and leads to higher syn anti rotation barriers about the carbon-carbon bond.

  DOI：

  10.1021/jo980507g
• 作为产物：
  描述：

  2-正己基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-(n-hexyl)-5-bromothiophene 1,1-dioxide
  参考文献：
  名称：

  Oligothiophene S,S-Dioxides. Synthesis and Electronic Properties in Relation to the Parent Oligothiophenes

  摘要：

  Oligothiophene S,S-dioxides from dimers to pentamers were obtained in good yields by reaction of mono- and dibrominated thiophene S,S-dioxides with the appropriate thienyl stannanes in the presence of Pd(AsPh3)(4) generated in situ. The reaction rate with brominated thiophene S,S-dioxides is greatly accelerated compared to that employing thienyl bromides to obtain the parent oligothiophenes. HF/6-31G* ab initio calculations on 2,2'-bithiophene and the corresponding mono- and bis-S,S-dioxides show that the functionalization of the thienyl sulfur to the S,S-dioxide does not affect the pi,pi* nature of the frontier orbitals, decreases the energy of the LUMO much more than that of the HOMO, increases the degree of planarity of the molecular skeleton, and leads to higher syn anti rotation barriers about the carbon-carbon bond.

  DOI：

  10.1021/jo980507g

文献信息

• [EN] NEW 3,4-ALKYLENEDIOXYTHIOPHENEDIOXIDE COMPOUNDS AND POLYMERS COMPRISING MONOMERIC UNITS THEREOF<br/>[FR] COMPOSES DE 3,4-ALKYLENEDIOXYTHIOPHENEDIOXYDE, ET POLYMERES COMPRENANT DES UNITES MONOMERES DE CES COMPOSES
  申请人：AGFA GEVAERT

  公开号：WO2004020444A1

  公开（公告）日：2004-03-11

  A 3,4-alkylenedioxythiophenedioxide compound; a polymer comprising monomeric units of at least one 3,4-alkylenedioxy-thiophenedioxide compound; an aqueous dispersion of a polymer comprising monomeric units corresponding to at least one 3,4-alkylenedioxythiophene-dioxide compound and a polyanion; a chemical polymerization process for preparing the aqueous dispersion comprising the steps of: (i) providing a solution of a polyanion; (ii) adding a 3,4-alkylene-dioxythiophenedioxide compound and a thiophene or pyrrole compound to the solution provided in step (i); and (iii) adding an oxidizing or reducing system to the mixture provided in step (ii); a printable paste containing the aqueous dispersion; an electroconductive layer containing the polymer; the use of the electroconductive layer in a light emitting diode; an antistatic layer containing the polymer; and an electroconductive pattern and a process for preparing the electroconductive pattern.

  一种3,4-烷基二氧杂苯并二氧化物化合物；一种聚合物，包含至少一种3,4-烷基二氧杂苯并二氧化物化合物的单体单位；一种水分散体，包含与至少一种3,4-烷基二氧杂苯并二氧化物化合物相对应的单体单位和一个聚阴离子；一种化学聚合过程，用于制备上述水分散体，包括以下步骤：（i）提供聚阴离子的溶液；（ii）将3,4-烷基二氧杂苯并二氧化物化合物和噻吩或吡咯化合物加入到步骤（i）提供的溶液中；（iii）向步骤（ii）提供的混合物中加入氧化或还原系统；一种可打印的浆料，包含上述水分散体；一种含有该聚合物的电导层；将该电导层用于发光二极管；一种含有该聚合物的抗静电层；以及一种制备电导图案的电导图案和制备过程。
• Molecular engineering of hybrid π-conjugated oligomers combining 3,4-ethylenedioxythiophene (EDOT) and thiophene-S,S-dioxide units
  作者：Manuela Melucci、Pierre Frère、Magali Allain、Eric Levillain、Giovanna Barbarella、Jean Roncali

  DOI：10.1016/j.tet.2007.07.006

  日期：2007.9

  are separated by unsubstituted thiophene cycles. Introduction of S,S-dioxide unit in the median position of the chain has a stronger effect on the lowering of the LUMO level while insertion of EDOT units at the lateral positions limits the decrease of the HOMO level. Consequently, the corresponding oligomers present the smallest electrochemical gap while electrooxidation leads directly to the dication

  基于噻吩，3，4-乙撑二氧噻吩（EDOT）和噻吩-S，S-二氧化物单元的各种组合，合成了一系列π共轭低聚物。理论计算，光学和电化学数据表明，共轭体系中EDOT和S，S-二氧化物单元的相对位置对其电子性能产生很大影响。EDOT单元在S，S-二氧化物单元位于侧向位置的共轭链内的插入导致呈现适度的带隙的平面共轭体系。与此相反，被取代的小号，小号位于主链内的-二氧化物单元产生共轭链的扭转。然而，当EDOT和S，S-二氧化物部分被未取代的噻吩环分开时，扭转角显着降低。在链的中间位置引入S，S-二氧化物单元对降低LUMO水平具有更强的作用，而在侧面位置插入EDOT单元则限制了HOMO水平的降低。因此，相应的低聚物呈现出最小的电化学间隙，而电氧化通过双电子过程直接导致了指示状态。
• 3,4-alkylenedioxythiophenedioxide compounds and polymers comprising monomeric units thereof
  申请人：AGFA-GEVAERT

  公开号：US20040097741A1

  公开（公告）日：2004-05-20

  A 3,4-alkylenedioxythiophenedioxide compound represented by formula 1 in which: A represents a C 1-5 -alkylene bridge; R represents an optionally substituted C 1-24 -alkyl, C 3-18 -cycloalkyl, C 1-18 -alkoxy or polyethylene oxide group (optionally with at least one substituent selected from the group consisting of an alcohol, amide, ether, ester or sulphonate group) or an optionally substituted aryl group; a polymer comprising monomeric units represented by formula (I); an aqueous dispersion of a polymer comprising monomeric units corresponding to at least one compound according to formula (I) and a polyanion; a chemical polymerization process for preparing the aqueous dispersion comprising the steps of: (i) providing a solution of a polyanion; (ii) adding a compound according to formula (I) and a thiophene or pyrrole compound to the solution provided in step (i); and (iii) adding an oxidizing or reducing system to the mixture provided in step (ii); a printable paste containing the aqueous dispersion; an electroconductive layer containing the polymer; the use of the electroconductive layer in a light emitting diode; an antistatic layer containing the polymer; and an electroconductive pattern and a process for preparing the electroconductive pattern.

  一种 3,4-烷基二氧噻吩二氧化物化合物，由式 1 代表 1 其中A 代表 C 1-5 -烯桥；R 代表任选取代的 C 1-24 -烷基、C 3-18 -环烷基、C 1-18 -烷氧基或聚环氧乙烷基团(可任选具有至少一个选自醇、酰胺、醚、酯或磺酸盐基团组成的组的取代基)或可任选取代的芳基；由式(I)代表的单体单元组成的聚合物；由与至少一种根据式(I)的化合物相对应的单体单元和聚阴离子组成的聚合物的水分散液；制备该水分散液的化学聚合工艺，包括以下步骤：(i) 提供聚阴离子溶液；(ii) 向步骤(i)中提供的溶液中加入根据式(I)的化合物和噻吩或吡咯化合物；(iii) 向步骤(ii)中提供的混合物中加入氧化或还原体系；含有水性分散体的可印刷浆料；含有聚合物的导电层；导电层在发光二极管中的用途；含有聚合物的抗静电层；以及导电图案和制备导电图案的工艺。
• US6927298B2
  申请人：——

  公开号：US6927298B2

  公开（公告）日：2005-08-09
• Oligothiophene <i>S</i>,<i>S</i>-Dioxides. Synthesis and Electronic Properties in Relation to the Parent Oligothiophenes
  作者：G. Barbarella、L. Favaretto、G. Sotgiu、M. Zambianchi、L. Antolini、O. Pudova、A. Bongini

  DOI：10.1021/jo980507g

  日期：1998.8.1

  Oligothiophene S,S-dioxides from dimers to pentamers were obtained in good yields by reaction of mono- and dibrominated thiophene S,S-dioxides with the appropriate thienyl stannanes in the presence of Pd(AsPh3)(4) generated in situ. The reaction rate with brominated thiophene S,S-dioxides is greatly accelerated compared to that employing thienyl bromides to obtain the parent oligothiophenes. HF/6-31G* ab initio calculations on 2,2'-bithiophene and the corresponding mono- and bis-S,S-dioxides show that the functionalization of the thienyl sulfur to the S,S-dioxide does not affect the pi,pi* nature of the frontier orbitals, decreases the energy of the LUMO much more than that of the HOMO, increases the degree of planarity of the molecular skeleton, and leads to higher syn anti rotation barriers about the carbon-carbon bond.