5,5'-dibromo-4,4'-dihexyl-2,2'-bithiophene-1,1,1',1'-tetraoxide | 1287297-38-4

• 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: 5,5'-dibromo-4,4'-dihexyl-2,2'-bithiophene-1,1,1',1'-tetraoxide
• 英文别名: 2-Bromo-5-(5-bromo-4-hexyl-1,1-dioxothiophen-2-yl)-3-hexylthiophene 1,1-dioxide；2-bromo-5-(5-bromo-4-hexyl-1,1-dioxothiophen-2-yl)-3-hexylthiophene 1,1-dioxide
• CAS: 1287297-38-4
• 化学式: C₂₀H₂₈Br₂O₄S₂
• 分子量: 556.38
• InChiKey: XYGNEGUAZLKBEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5'-dibromo-4,4'-dihexyl-2,2'-bithiophene-1,1,1',1'-tetraoxide 、 苯基乙炔三丁基锡 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以65%的产率得到5,5'-bis-(2-phenylethynyl)-4,4'-dihexyl-2,2'-bithiophene-1,1,1',1'-tetraoxide
  参考文献：
  名称：

  包含内部[[]]-S，S-氧合噻吩片段内部相邻序列的新型共轭寡聚噻吩

  摘要：

  寻求获得具有更窄的HOMO-LUMO间隙和更高的氧化还原电位的共轭含低聚噻吩的分子是本研究的主题。制备并研究了包含四联噻吩（2）和六噻吩（3）部分的分子。他们被氧原子转移到与所述HOF相应二溴低聚噻吩得到⋅ CH 3CN络合物，然后将它们与噻吩或乙炔锡衍生物交叉偶联。产品的光物理和电化学研究表明，与任何其他排列的低聚噻吩（包括各种[所有] -S，S-氧代噻吩衍生物）相比，这种特殊类型的混合噻吩的特征是明显更小的前沿轨道间隙以及更高的氧化和还原电势。

  DOI：

  10.1002/chem.201203936
• 作为产物：
  描述：

  2-溴-3-己基噻吩 在 potassium fluoride 、 二(氰基苯)二氯化钯 、 silver nitrate 、 hypofluorous acid acetonitrile complex 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 5,5'-dibromo-4,4'-dihexyl-2,2'-bithiophene-1,1,1',1'-tetraoxide
  参考文献：
  名称：

  可溶性低带隙低聚噻吩-[all] -S，S-二氧化物基共轭低聚物和聚合物的合成与表征

  摘要：

  可溶性oligothiophene-的一个新家族的合成和表征小号，小号-dioxides以及它们作为积木形成polythiophene-使用小号，小号通过微波辅助Stille偶联聚合描述-dioxides。将砜基团并入聚噻吩主链中会导致聚合物带隙变窄，同时聚噻吩S，S和相对于聚噻吩，二氧化物的含量更低，这种趋势对于最低的未占据分子轨道要比最高的占据分子轨道强得多，从而导致更大的电子接受能力。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年

  DOI：

  10.1002/pola.24641

文献信息

• [EN] MOLECULAR COMPOSITIONS, MATERIALS, AND METHODS FOR EFFICIENT MULTIPLE EXCITON GENERATION<br/>[FR] COMPOSITIONS MOLÉCULAIRES, MATÉRIAUX ET PROCÉDÉS PERMETTANT UNE GÉNÉRATION EFFICACE DE MULTIPLES EXCITONS
  申请人：UNIV COLUMBIA

  公开号：WO2015164831A9

  公开（公告）日：2015-12-30
• MOLECULAR COMPOSITIONS, MATERIALS, AND METHODS FOR EFFICIENT MULTIPLE EXCITION GENERATION
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US20170141318A1

  公开（公告）日：2017-05-18

  Embodiments of the present invention provides compounds, compositions, and methods for their preparation that provide efficient intramolecular fission, such that local order and strong nearest neighbor coupling is no longer a design constraint. Inventive materials include organic oligomers and polymers designed to exhibit strong intrachain donor-acceptor interactions and provide intramolecular singlet fission, whereby triplet populations can be generated in very high yields of, e.g., 170% or more. The inventive disclosure is directed to polymers of the general formula: [SA-SD]n with a strong electron acceptor (SA), a strong electron donor (SD), and n a positive integer equal to or greater than two; methods for their preparation and monomers used therein, blends, mixtures and formulations containing them; the use of the polymers, blends, mixtures and formulations as semiconductors in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, and to OE and OPV devices comprising these polymers, blends, mixtures or formulations.
• [EN] DESIGN STRATEGY FOR INTRAMOLECULAR SINGLET FISSION MEDIATED BY CHARGE-TRANSFER STATES IN DONOR-ACCEPTOR ORGANIC MATERIALS<br/>[FR] STRATÉGIE DE CONCEPTION POUR FISSION INTRAMOLÉCULAIRE DE SINGULETS À MÉDIATION ASSURÉE PAR DES ÉTATS DE TRANSFERT DE CHARGE DANS DES MATÉRIAUX ORGANIQUES DONNEUR-ACCEPTEUR
  申请人：UNIV COLUMBIA

  公开号：WO2016105533A1

  公开（公告）日：2016-06-30

  Embodiments of the present invention provides compounds, compositions, and methods for their preparation that provide efficient intramolecular fission, such that local order and strong nearest neighbor coupling is no longer a design constraint. Inventive materials include organic oligomers and polymers designed to exhibit strong intrachain donor-acceptor interactions and provide intramolecular singlet fission, whereby triplet populations can be generated in very high yields of, e.g., 170% or more. The inventive disclosure is directed to polymers of the general formula: [SA-SD]n with a strong electron acceptor (SA), a strong electron donor (SD), and n a positive integer equal to or greater than two; methods for their preparation and monomers used therein, blends, mixtures and formulations containing them; the use of the polymers, blends, mixtures and formulations as semiconductors in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, and to OE and OPV devices comprising these polymers, blends, mixtures or formulations.
• New Conjugated Oligothiophenes Containing the Unique Arrangement of Internal Adjacent [All]-<i>S,S</i>-Oxygenated Thiophene Fragments
  作者：Shay Potash、Shlomo Rozen

  DOI：10.1002/chem.201203936

  日期：2013.4.22

  obtaining conjugated oligothiophene‐containing molecules with narrower HOMO–LUMO gaps and higher oxidation and reduction potentials is the subject of this study. Molecules containing the bithiophene tetraoxide (2) and the terthiophene hexaoxide (3) moieties were prepared and studied. They were obtained by transferring oxygen atoms to the corresponding dibromo oligothiophenes with the HOF⋅CH3CN complex and then

  寻求获得具有更窄的HOMO-LUMO间隙和更高的氧化还原电位的共轭含低聚噻吩的分子是本研究的主题。制备并研究了包含四联噻吩（2）和六噻吩（3）部分的分子。他们被氧原子转移到与所述HOF相应二溴低聚噻吩得到⋅ CH 3CN络合物，然后将它们与噻吩或乙炔锡衍生物交叉偶联。产品的光物理和电化学研究表明，与任何其他排列的低聚噻吩（包括各种[所有] -S，S-氧代噻吩衍生物）相比，这种特殊类型的混合噻吩的特征是明显更小的前沿轨道间隙以及更高的氧化和还原电势。
• Synthesis and characterization of soluble low-bandgap oligothiophene-[all]-<i>S,S</i> -dioxides-based conjugated oligomers and polymers
  作者：Elizabeth Amir、Kulandaivelu Sivanandan、Justin E. Cochran、John J. Cowart、Sung-Yu Ku、Jung Hwa Seo、Michael L. Chabinyc、Craig J. Hawker

  DOI：10.1002/pola.24641

  日期：2011.5.1

  The synthesis and characterization of a new family of soluble oligothiophene‐S,S‐dioxides and their use as building blocks to form polythiophene‐S,S‐dioxides via microwave‐assisted Stille coupling polymerization are described. Incorporation of the sulfone group into the polythiophene backbone leads to narrowing of the polymer bandgap, and while the energies of both Frontier orbitals in polythiophene‐S

  可溶性oligothiophene-的一个新家族的合成和表征小号，小号-dioxides以及它们作为积木形成polythiophene-使用小号，小号通过微波辅助Stille偶联聚合描述-dioxides。将砜基团并入聚噻吩主链中会导致聚合物带隙变窄，同时聚噻吩S，S和相对于聚噻吩，二氧化物的含量更低，这种趋势对于最低的未占据分子轨道要比最高的占据分子轨道强得多，从而导致更大的电子接受能力。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年