3,4-二硝基-2,5-二噻吩-2-基噻吩 | 205170-72-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 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
• 中文名称: 3,4-二硝基-2,5-二噻吩-2-基噻吩
• 中文别名: 2.5-二(2-噻吩基)-3.4-二硝基噻吩
• 英文名称: 3',4'-dinitro-2,2':5',2''-terthiophene
• 英文别名: 2,5-Bis(2-thienyl)-3,4-dinitrothiophene；3,4-dinitro-2,5-dithiophen-2-ylthiophene
• CAS: 205170-72-5
• 化学式: C₁₂H₆N₂O₄S₃
• 分子量: 338.389
• InChiKey: IPTUQHNCFXOVAT-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C(Solv: ethanol (64-17-5))
• 沸点：
  492.3±45.0 °C(Predicted)
• 密度：
  1.595±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 危险类别：
  4.1
• 危险性防范说明：
  P501,P270,P240,P210,P241,P264,P280,P302+P352,P370+P378,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险品运输编号：
  1325
• 危险性描述：
  H302,H315,H319,H228
• 包装等级：
  III
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3,4-二硝基-2,5-二噻吩-2-基噻吩 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 83.0h， 生成 2,3-bis(N,N-diethylaminomethyl)-5,7-bis(2-thienyl)thieno[3,4-b]pyrazine
  参考文献：
  名称：

  Synthesis and Characterization of Thieno[3,4-b]pyrazine-Based Terthienyls: Tunable Precursors for Low Band Gap Conjugated Materials

  摘要：

  Synthetic methods have been developed for the preparation of new 2,3-dihalo- and 2,3-ditriflato-5,7-bis(2-thienyl)thieno[3,4-b]pyrazines. From these reactive intermediates, a variety of new 2,3-difunctionalized 5,7-bis(2-thienyl)-thieno[3,4-b]pyrazines have been produced as precursors to conjugated materials. Structural, electronic, and optical characterization of these new analogues illustrate the extent to which the electronic nature of the functional groups can be used to tune the electronic properties of these thieno[3,4-b]pyrazine-based terthienyl units.

  DOI：

  10.1021/jo400577q
• 作为产物：
  描述：

  2,5-二溴-3,4-二硝基噻吩 、 2-(trimethylstannyl)thiophene 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以75%的产率得到3,4-二硝基-2,5-二噻吩-2-基噻吩
  参考文献：
  名称：

  Kamal, Marwan R.; Al-Taweel, Samir A.; El-Abadelah, Mustafa M., Phosphorus, Sulfur and Silicon and the Related Elements, 1997, vol. 126, p. 65 - 74

  摘要：

  DOI：

文献信息

• Anionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold
  作者：Tyll Freese、Ana-Luiza Lücke、Catharina A.S. Schmidt、Mika Polamo、Martin Nieger、Jan C. Namyslo、Andreas Schmidt

  DOI：10.1016/j.tet.2017.07.032

  日期：2017.9

  The sydnone imines Molsidomine and 5-(benzoylimino)-3-(2-methoxyphenyl)-1,2,3-oxadiazolium-2-ide gave anionic N-heterocyclic carbenes on deprotonation at C4 which were trapped as methylated selenium adducts, gold complexes (X-ray analysis) as well as palladium complexes (X-ray analysis). The 13C NMR resonance frequencies of the carbene carbon atom are extremely shifted upfield and appear at δ = 142

  sydnone亚胺的Molsidomine和5-（苯甲酰亚氨基）-3-（2-甲氧基苯基）-1,2,3-恶二唑-2-胺在C4脱质子化后得到阴离子N-杂环卡宾，以甲基化硒加合物，金配合物的形式被捕集（X射线分析）以及钯配合物（X射线分析）。卡宾碳原子的13 C NMR共振频率向高场偏移，并且出现在δ  = 142.1 ppm（莫西多明卡宾）和δ  = 159.8 ppm（亚砜亚胺卡宾）上。Pd配合物在Suzuki-Miyaura和Sonogashira-Hagihara交叉偶联反应中用作催化剂。
• DEVICE FOR REGULATING THE PASSAGE OF ENERGY
  申请人：Merck Patent GmbH

  公开号：US20170267929A1

  公开（公告）日：2017-09-21

  The present application relates to a device for regulating the passage of energy from an outside space into an inside space, to compounds, windows and uses of the devices and compounds.

  本发明涉及一种调节能量从外部空间进入内部空间的装置，以及化合物、窗户和该装置及化合物的用途。
• Pyrazine-incorporating panchromatic sensitizers for dye sensitized solar cells under one sun and dim light
  作者：Mulu Berhe Desta、Nguyễn Sơn Vinh、CH. Pavan Kumar、Sumit Chaurasia、Wei-Ti Wu、Jiann T. Lin、Tzu-Chien Wei、Eric Wei-Guang Diau

  DOI：10.1039/c8ta04774j

  日期：——

  π-conjugated bridge, and A = electron acceptor/anchor) sensitizers with two bis(alkoxy)phenyl substituents incorporating thieno[3,4-b]pyrazines (TP) or a benzo[3,4-b]pyrazine (BP) entity as the auxiliary acceptor have been synthesized for application in dye-sensitized solar cells (DSSCs). Under 1 sun illumination, the DSSCs fabricated from the two BP dyes with a co-adsorbent have efficiencies of 8.39% and

  新型D–A'–π–A型（D =电子供体，A'=辅助受体，π=π共轭桥，A =电子受体/锚）敏化剂，带有两个结合噻吩并[3]的双（烷氧基）苯基取代基，4- b ]吡嗪（TP）或苯并[3,4 b ]吡嗪（BP）实体作为辅助受体已被合成为在染料敏化太阳能电池（DSSC）应用程序。在1个阳光照射下，由两种BP染料与助吸附剂制成的DSSC的效率分别为8.39％和9.03％。后者超过了标准的N719染料（8.87％）。在昏暗的光线条件下MD7 在300 lux和6000 lux的辐照度下，功率转换效率分别为18.95％和27.17％。
• Synthesis of Thieno[3,4-<i>b</i>]pyrazine-Based and 2,1,3-Benzothiadiazole-Based Donor−Acceptor Copolymers and their Application in Photovoltaic Devices
  作者：Erjun Zhou、Junzi Cong、Shimpei Yamakawa、Qingshuo Wei、Motoshi Nakamura、Keisuke Tajima、Chunhe Yang、Kazuhito Hashimoto

  DOI：10.1021/ma100039q

  日期：2010.3.23

  of 5,7-dithien-2-yl-thieno[3,4-b]pyrazine (DTTP)-based donor−acceptor (D−A) copolymers (TP1-6) and three types of 5,7-dithien-2-yl-2,1,3-benzothiadiazole (DTBT)-based D−A copolymers (PF-DTBT, PC-DTBT, and PIC-DTBT). The optical properties, electrochemical behavior, and energy levels of these nine copolymers were investigated. The photovoltaic performance of the copolymers was compared and discussed

  两种基于噻吩并[3,4- b ]吡嗪的单体，2,3-二甲基-5,7-二（2-溴噻吩-5-基）-噻吩并[3,4- b ]吡嗪和2,3通过改进的合成途径合成了-二苯基-5,7-二（2-溴噻吩-5-基）-噻吩并[3,4- b ]吡嗪。通过铃木交叉偶联反应，将这两种单体和4,7-二（2-溴噻吩-5-基）-2,1,3-苯并噻二唑分别与三个供体链段（芴，咔唑和吲哚并咔唑）共聚，得到六种类型的5,7-二噻吩-2-基-噻吩[3,4- b]吡嗪（DTTP）为基础的供体受体（DAA）共聚物（TP1-6）和三种5,7-二噻吩-2-基-2,1,3-苯并噻二唑（DTBT）为基础的D-A共聚物（PF-DTBT，PC-DTBT和PIC-DTBT）。研究了这九种共聚物的光学性质，电化学行为和能级。比较并讨论了共聚物的光伏性能，并考虑了它们的能级。
• Iron(II) complexes containing thiophene-substituted “bispicen” ligands — Spin-crossover, ligand rearrangements, and ferromagnetic interactions
  作者：Haojin Cheng、Brandon Djukic、Hilary A. Jenkins、Serge I. Gorelsky、Martin T. Lemaire

  DOI：10.1139/v10-086

  日期：2010.9

  The synthesis and characterization of three new tetradentate “bispicen-type” ligands containing a substituted thiophene heterocycle are described [2,5-thienyl substituents = H (7), Ph (8), or 2-thienyl (9)]. Iron(II) bis(thiocyanate) coordination complexes containing 7–9 were prepared, and the electronic and variable-temperature magnetic properties of complexes containing 7 (10) and 9 (12) are described. Complex 10 features a gradual and incomplete spin crossover in the solid state, and 12 remains high-spin over the entire temperature range. Complex 11 is extremely unstable and rearranges to another iron(II) complex (13), which was structurally characterized. The temperature-dependent magnetic properties of 13 are described as a one-dimensional ferromagnetic chain, with interchain antiferromagnetic interactions and (or) zero-field splitting dominant at low temperatures. The magnetic analysis is corroborated by the molecular packing and density functional theory calculations, which suggest intermolecular interactions between coordinated thiocyanate ligands bearing a significant spin density.

  介绍了含有取代噻吩杂环的三种新的四价 "双噻吩型 "配体[2,5-噻吩基取代基 = H (7)、Ph (8) 或 2-噻吩基 (9)]的合成和特性。制备了含有 7-9 的双硫氰酸铁（II）配位配合物，并描述了含有 7（10）和 9（12）的配合物的电子和变温磁性。络合物 10 在固态下具有渐进和不完全的自旋交叉，而络合物 12 在整个温度范围内都保持高自旋。络合物 11 极不稳定，会重新排列成另一种铁（II）络合物（13），并对其进行了结构表征。13 的磁性随温度变化，被描述为一维铁磁链，链间反铁磁相互作用和（或）零场分裂在低温下占主导地位。分子堆积和密度泛函理论计算证实了这一磁性分析。