4,7-二(2-噻吩基)噻吩并[3,4-C]吡啶 | 1007128-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4,7-二(2-噻吩基)噻吩并[3,4-C]吡啶
• 英文名称: 4,7-dithienyl[1,2,5]thiadiazolo[3,4-c]pyridine
• 英文别名: 4,7-dithienyl[1,2,5]thiadiazole[3,4-c]pyridine；Th-PT-Th；4,7-Di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine；4,7-dithiophen-2-yl-[1,2,5]thiadiazolo[3,4-c]pyridine
• CAS: 1007128-74-6
• 化学式: C₁₃H₇N₃S₃
• 分子量: 301.417
• InChiKey: VIIFSDQVOHEEHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,7-二(2-噻吩基)噻吩并[3,4-C]吡啶 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 72.7h， 生成 bis{2-thienyl-(4,4-bis(n-hexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene)}-4,7-pyridal[2,1,3]thiadiazole
  参考文献：
  名称：

  窄带隙共轭聚合物的路易斯酸加合物

  摘要：

  我们报告了路易斯酸与包含供体和受体单元的窄带隙共轭共聚物的相互作用。广泛使用的聚[(4,4-双(2-乙基己基)环戊二烯-[2,1-b:3,4-b']二噻吩)-2,6-(diyl-alt-benzo[2, 1,3]噻二唑)-4,7-二基] (1) 与包含环戊二烯-[2,1-的小分子相比，与 B(C(6)F(5))(3) 的结合较弱b:3,4-b'] 二噻吩 (CDT) 单元两侧是两个苯并 [2,1,3] 噻二唑 (BT) 片段。对代表 1 的模型化合物的研究，以及 B(C(6)F(5))(3) 和 BBr(3) 之间的比较，表明由于 BT 周围的空间阻碍，路易斯酸配位的倾向降低氮位点。这些观察结果导致了发色团的​​设计，这些发色团包含一个受体单元和一个更碱性的氮位点，即吡啶[2，1,3]噻二唑 (PT)。通过检查 B(C(6)F(5))(3) 与两个小分子 bis(4,4-bis(hexyl)-4H-cyclopenta)

  DOI：

  10.1021/ja110968m
• 作为产物：
  描述：

  3,4-二氨基吡啶 在 tris-(dibenzylideneacetone)dipalladium(0) 、 氢溴酸 、 溴 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 4,7-二(2-噻吩基)噻吩并[3,4-C]吡啶
  参考文献：
  名称：

  High-mobility low-bandgap conjugated copolymers based on indacenodithiophene and thiadiazolo[3,4-c]pyridine units for thin film transistor and photovoltaic applications

  摘要：

  通过斯蒂尔偶联聚合法合成了两种基于茚并二噻吩和噻二唑并[3,4-c]吡啶单元的新型半导体聚合物。聚合物 PIDTPyT 和 PIDTDTPyT 在 550-800 纳米范围内显示出主要吸收带，而它们在薄膜中的吸收最大值位于 700 纳米左右。与 PIDTPyT 相比，带有两个额外噻吩间隔的 PIDTDTPyT 的吸收带更宽，但最大峰值蓝移了 20 纳米。这两种聚合物都具有较低的带隙（1.6 eV）和较深的最高占位分子轨道（HOMO）和最低未占位分子轨道（LUMO）能级。有机场效应晶体管（OFET）器件测量结果表明，PIDTPyT 和 PIDTDTPyT 的空穴载流子迁移率分别高达 0.066 和 0.045 cm2 V-1s-1，导通/截止比约为 106。由共聚物和 PC71BM 组成的块状异质结光伏器件的功率转换效率（PCE）高达 3.91%，在 300-800 纳米范围内具有宽带光响应。本文讨论了光伏性能与薄膜形态、能级和空穴迁移率之间的关系。

  DOI：

  10.1039/c1jm11564b

文献信息

• Band gap control in conjugated oligomers and polymers via Lewis acids
  申请人：Bazan Guillermo C.

  公开号：US20110028656A1

  公开（公告）日：2011-02-03

  A method for altering the electronic and optical properties of a chemical compound having a band gap and a framework that includes π-delocalized electrons. The method includes complexing a Lewis acid to a basic site within the framework to form a Lewis acid adduct having a band gap that differs from the band gap of the chemical compound. The λ max of the Lewis acid adduct can be shifted to a longer wavelength in comparison to the λ max of the chemical compound. In various versions, the chemical compound can be a conjugated oligomer, a conjugated polymer, or a small molecule comprising a conjugated π-electron system. Electronic devices that include Lewis acid adducts are also provided.

  一种改变具有带隙和包含π-离域电子的化合物的电子和光学性质的方法。该方法包括将Lewis酸络合到框架内的碱性位点，形成具有与化合物不同带隙的Lewis酸加合物。与化合物的λmax相比，Lewis酸加合物的λmax可以向更长波长移动。在各种版本中，化合物可以是共轭寡聚体、共轭聚合物或包含共轭π-电子系统的小分子。还提供包括Lewis酸加合物的电子器件。
• LUMINESCENT SOLAR CONCENTRATOR COMPRISING DITHIENYLPYRIDINETHIADIOAZOLE COMPOUNDS
  申请人：ENI S.P.A.

  公开号：US20210320262A1

  公开（公告）日：2021-10-14

  Luminescent solar concentrator (LSC) having at least one dithienylpyridinethiadiazole compound having general formula (I) or (II): Said luminescent solar concentrator (LSC) can be advantageously used in the construction of photovoltaic devices (or solar devices) selected, for example, from photovoltaic cells (or solar cells), photovoltaic modules (or solar modules), both on rigid support, and on flexible support.

  具有至少一个具有通式（I）或（II）的二噻吩基吡啶硫代唑化合物的发光太阳能聚光器（LSC）：所述的发光太阳能聚光器（LSC）可以优势地用于光伏器件（或太阳能器件）的制造，例如从光伏电池（或太阳能电池），光伏模块（或太阳能模块），无论是在刚性支撑上还是在柔性支撑上。
• Toward a Rational Design of Poly(2,7-Carbazole) Derivatives for Solar Cells
  作者：Nicolas Blouin、Alexandre Michaud、David Gendron、Salem Wakim、Emily Blair、Rodica Neagu-Plesu、Michel Belletête、Gilles Durocher、Ye Tao、Mario Leclerc

  DOI：10.1021/ja0771989

  日期：2008.1.1

  On the basis of theoretical models and calculations, several alternating polymeric structures have been investigated to develop optimized poly(2,7-carbazole) derivatives for solar cell applications. Selected low band gap alternating copolymers have been obtained via a Suzuki coupling reaction. A good correlation between DFT theoretical calculations performed on model compounds and the experimental HOMO, LUMO, and band gap energies of the corresponding polymers has been obtained. This study reveals that the alternating copolymer HOMO energy level is mainly fixed by the carbazole moiety, whereas the LUMO energy level is mainly related to the nature of the electron-withdrawing comonomer. However, solar cell performances are not solely driven by the energy levels of the materials. Clearly, the molecular weight and the overall organization of the polymers are other important key parameters to consider when developing new polymers for solar cells. Preliminary measurements have revealed hole mobilities of about 1 x 10(-3) cm(2).V-1.s(-1) and a power conversion efficiency (PCE) up to 3.6%. Further improvements are anticipated through a rational design of new symmetric low band gap poly(2,7-carbazole) derivatives.
• US8343382B2
  申请人：——

  公开号：US8343382B2

  公开（公告）日：2013-01-01
• [EN] LUMINESCENT SOLAR CONCENTRATOR COMPRISING DITHIENYLPYRIDINETHIADIOAZOLE COMPOUNDS<br/>[FR] CONCENTRATEUR SOLAIRE LUMINESCENT COMPRENANT DES COMPOSÉS DE TYPE DITHIÉNYLPYRIDINETHIADIAZOLE
  申请人：ENI SPA

  公开号：WO2020129018A1

  公开（公告）日：2020-06-25

  Luminescent solar concentrator (LSC) comprising at least one dithienylpyridinethiadiazole compound having general formula (I) or (II): wherein: R1, R2, R3, R4, R5 and R6, mutually identical or different, represent a hydrogen atom; or they are selected from linear or branched, saturated or unsaturated C1-C20, preferably C1-C8, alkyl groups, optionally containing heteroatoms, optionally substituted aryl groups, optionally substituted heteroaryl groups; R7, mutually identical or different, represent a hydrogen atom; or they are selected from linear or branched, saturated or unsaturated C1-C20, preferably C1-C8, alkyl groups, optionally containing heteroatoms, optionally substituted aryl groups, optionally substituted heteroaryl groups, optionally substituted phenoxy groups; or R1 and R2 or R2 and R3, and/or R4 and R5 or R5 and R6, can be optionally linked together so as to form, together with the carbon atoms to which they are linked, a saturated, unsaturated, or aromatic, cycle or polycyclic system containing from 3 to 14 carbon atoms, preferably from 4 to 6 carbon atoms, optionally containing one or more heteroatoms such as, for example, oxygen, sulfur, nitrogen, silicon, phosphorus, selenium; Y represents a divalent cyclic or polycyclic group containing one or more aromatic or heteroaromatic rings, said aromatic or heteroaromatic rings being optionally substituted; n is 0 or 1; p is 0 or 1. Said luminescent solar concentrator (LSC) can be advantageously used in the construction of photovoltaic devices (or solar devices) selected, for example, from photovoltaic cells (or solar cells), photovoltaic modules (or solar modules), both on rigid support, and on flexible support.