EA671;;二噻吩[3,2-E:2,3-G]-2,1,3-苯并噻二唑 | 1256138-50-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 中文名称: EA671;;二噻吩[3,2-E:2,3-G]-2,1,3-苯并噻二唑
• 英文名称: dithieno[3',2':3,4;2'',3'':5,6]benzo[1,2-c][1,2,5]thiadiazole
• 英文别名: dithieno[3′,2′:3,4;2″,3″:5,6]benzo[1,2-c][1,2,5]thiadiazole；dithieno[3′,2’:3,4;2′′,3’’:5,6]benzo[1,2-c][1,2,5]thiadiazole；4,10,13-trithia-3,5-diazatetracyclo[10.3.0.02,6.07,11]pentadeca-1(12),2,5,7(11),8,14-hexaene
• CAS: 1256138-50-7
• 化学式: C₁₀H₄N₂S₃
• 分子量: 248.353
• InChiKey: YLKKIBOMGQAGGA-UHFFFAOYSA-N

物化性质

• 沸点：
  444.9±25.0 °C(Predicted)
• 密度：
  1.693±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  EA671;;二噻吩[3,2-E:2,3-G]-2,1,3-苯并噻二唑 在 溴 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以94%的产率得到5,8-二溴二噻吩并[3',2':3,4;2'',3'':5,6]苯并[1,2-c][1,2,5]噻二唑
  参考文献：
  名称：

  钙钛矿型太阳能电池含硒的DA-D-D型无掺杂空穴传输材料

  摘要：

  设计，合成了一种新型的含二硫杂苯并二硒代苯并二氮杂唑受体单元（DTBS）的含硒DA-D-D型无掺杂空穴传输材料，并将其应用于钙钛矿型太阳能电池（PSC）中。此外，两个自由掺杂物的空穴传输材料制备成具有相似的结构，但不同的硫族元素（O为引用DTBF和S为DTBT正在使用）。系统地研究了无掺杂空穴传输材料中硫族元素原子变化对性能的影响，如PSC中的物理化学，电化学，形态特征和光电性能。用DTBS制成的PSC示出了由于其高填充因子，这是比用的参考文献中（13.31％为高得多的15.09％的功率转换效率值DTBF和11.65％DTBT）。此外，用DTBS制成的未封装的PSC在30天后的空气条件下仍可保持77.8％的性能，这比用掺杂的Spiro-OMeTAD制成的PSC（43.6％）要好得多。对于大稳定性DTBS的基于PSC可由于的优良薄膜形态和疏水性DTBS。我们的工作表明，含硒的有机化合物可以用

  DOI：

  10.1016/j.dyepig.2021.109339
• 作为产物：
  描述：

  4,7-二溴-5,6-二氟-苯并噻二唑 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodiumsulfide nonahydrate 、 二异丙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.17h， 生成 EA671;;二噻吩[3,2-E:2,3-G]-2,1,3-苯并噻二唑
  参考文献：
  名称：

  Facile Synthesis of Dithienobenzothiadiazoles and D18−Cl Polymer via Na2S‐Mediated Rapid Thiophene‐Annulations for Organic Solar Cells

  摘要：

  We present a novel synthetic route for the rapid construction of dithieno[3′,2′:3,4;2′′,3′′:5,6]benzo[1,2‐c][1,2,5]thiadiazoles via Na2S‐promoted thiophene annulation. This method facilitated the synthesis of D18−Cl polymer, known for its efficacy as a polymer donor in bulk‐heterojunction polymer solar cells. Starting from commercially available 4,7‐dihalo‐5,6‐difluorobenzo[c][1,2,5]thiadiazole, various 4,7‐dialkynylated compounds were obtained through Sonogashira reaction conditions. Subsequent Na2S‐promoted thiophene annulations yielded DTBT and its derivatives in excellent yields within 10 minutes. DTBT was then utilized as a precursor for the concise synthesis of D18−Cl, benefiting from reduced synthetic steps, mild reaction conditions, decreased complexity, and high overall yields. In another route, a space group‐bridged DTBT was directly constructed via Na2S‐promoted thiophene annulations and converted into D18−Cl through a couple of steps. This developed protocol offers a straightforward and reliable synthetic tool, conducive to reducing complexities in the production of DTBT‐based organic electronic materials, thereby advancing the potential commercialization of organic solar cells.

  DOI：

  10.1002/cssc.202400055

文献信息

• A Facile Synthesized Polymer Featuring B‐N Covalent Bond and Small Singlet‐Triplet Gap for High‐Performance Organic Solar Cells
  作者：Shuting Pang、Zhiqiang Wang、Xiyue Yuan、Langheng Pan、Wanyuan Deng、Haoran Tang、Hongbin Wu、Shanshan Chen、Chunhui Duan、Fei Huang、Yong Cao

  DOI：10.1002/anie.202016265

  日期：2021.4.12

  OSC, comparable to the benzo[1,2‐b:4,5‐b′]dithiophene (BDT)‐based counterpart. The nonradiative recombination energy loss of 0.19 eV was afforded by PBNT‐BDD. PBNT‐BDD also exhibited weak crystallinity and appropriate miscibility with Y6‐BO, benefitting of morphological stability. The singlet–triplet gap (ΔEST) of PBNT‐BDD is as low as 0.15 eV, which is much lower than those of common organic semiconductors

  高效有机太阳能电池（OSC）很大程度上依赖于聚合物供体。在本文中，我们报告了一种新的构建基BNT和具有B-N共价键的相关聚合物PBNT-BDD，可用于OSC。BNT单元仅需3个步骤即可合成，因此可以轻松实现PBNT-BDD的合成。与非富勒烯受体Y6-BO混合时，PBNT-BDD在OSC中的功率转换效率（PCE）为16.1％，与苯并[1,2-b：4,5-b']二噻吩（BDT）相当基于对应项。PBNT-BDD提供的非辐射重组能量损失为0.19 eV。PBNT-BDD还表现出弱结晶性，并与Y6-BO具有适当的混溶性，这有利于形态稳定性。单重态-三重态间隙（ΔE STPBNT-BDD的）低至0.15 eV，远低于常见的有机半导体（≥0.6eV）。结果，PBNT-BDD的三重态高于电荷转移（CT）状态，这将有效地抑制通过三重态的重组。
• The effect of thiadiazole out-backbone displacement in indacenodithiophene semiconductor polymers
  作者：Miquel Planells、Mark Nikolka、Michael Hurhangee、Pabitra S. Tuladhar、Andrew J. P. White、James R. Durrant、Henning Sirringhaus、Iain McCulloch

  DOI：10.1039/c4tc01500b

  日期：——

  We explore the effect of moving the well-known thiadiazole unit away from the polymer backbone on polymer optoelectronic properties and ultimately on device performance.

  我们探讨了将著名的噻二唑单元从聚合物骨架中移开对聚合物光电性能以及最终器件性能的影响。
• [EN] LUMINESCENT MATERIALS AND METHODS THEREOF<br/>[FR] MATÉRIAUX LUMINESCENTS ET PROCÉDÉS ASSOCIÉS
  申请人：UNIV WASHINGTON

  公开号：WO2021062035A1

  公开（公告）日：2021-04-01

  The present disclosure features a luminescent molecule, including a luminophore (e.g., a fluorescent dye); and a moiety including a heteroaryl core covalently and directly bonded to the luminophore. The luminescent molecule has an increased photoluminescence quantum yield relative to an analogous luminophore without a covalently bonded moiety including the heteroaryl core.

  本公开涉及一种发光分子，包括一种发光团（例如，荧光染料）；以及一种包括与发光团共价直接连接的杂芳基核的基团。该发光分子相对于不包括包括杂芳基核的共价连接基团的类似发光团具有增加的光致发光量子产率。
• POLYCYCLIC DITHIOPHENES
  申请人：Kirner Hans Jürg

  公开号：US20120097935A1

  公开（公告）日：2012-04-26

  The present invention relates to novel compounds of the formula (I) wherein R 1 and R 1 ′ independently of each other are H or a substituent, halogen or SiR 6 R 4 R 5 ; R 2 and R 2 ′ may be the same or different and are selected from C 1 -C 25 alkyl, C 3 -C 12 -cycloalkyl, C 2 -C 25 alkenyl, C 2 -C 25 alkynyl, C 4 -C 25 aryl, C 5 -C 25 alkylaryl or C 5 -C 25 aralkyl, each of which is unsubstituted or substituted, and under conditions as defined in claim 1, R2 and/or R2′ may also be halogen or hydrogen; X is a divalent linking group selected from formula (Ia) and formula (Ib); Y and Y′ independently are selected from formula (Ic), formula (Id), formula (Ie), formula (If), formula (Ig); n and p independently range from 0 to 6; where further symbols are as defined in claim 1, and to corresponding oligomers and (co)polymers. The compounds according to the invention are useful as semiconductors and have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers according to the invention are used in organic field effect transistors, organic photovoltaics (solar cells) and photodiodes.

  本发明涉及具有以下结构的新化合物（I）： 其中R1和R1'独立地为H或取代基，卤素或SiR6R4R5；R2和R2'可以相同也可以不同，选择自C1-C25烷基，C3-C12环烷基，C2-C25烯基，C2-C25炔基，C4-C25芳基，C5-C25烷基芳基或C5-C25芳基烷基，每种未取代或取代，并且在如权利要求1中定义的条件下，R2和/或R2'也可以是卤素或氢；X是从式（Ia）和式（Ib）中选择的二价连接基；Y和Y'独立地从式（Ic）、式（Id）、式（Ie）、式（If）、式（Ig）中选择；n和p独立地范围从0到6；其中进一步的符号如权利要求1中所定义的那样，以及相应的寡聚体和（共）聚合物。根据本发明的化合物可用作半导体，在有机溶剂中具有优异的溶解性和优良的成膜性能。此外，当根据本发明的聚合物用于有机场效应晶体管、有机光伏（太阳能电池）和光电二极管时，可以观察到高效的能量转换效率，优异的场效应迁移率，良好的开/关电流比和/或优异的稳定性。
• Naphthoindacenodithiophenes and polymers
  申请人：CLAP Co., Ltd.

  公开号：US10793668B2

  公开（公告）日：2020-10-06

  Polymers comprising at least one unit of formula 1 and compounds of the formula 1′ wherein, in formulae 1 and 1′ n is 0, 1, 2, 3 or 4 m is 0, 1, 2, 3 or 4 X is at each occurrence selected from the group consisting of O, S, Se or Te, Q is at each occurrence selected from the group consisting of C, Si or Ge R is at each occurrence selected from the group consisting of hydrogen, C1-30-alkyl, C2-30-alkenyl, C2-30-alkynyl, C5-12-cycloalkyl, C6-18-aryl, R2, R2′, R* are at each occurrence independently selected from the group consisting of hydrogen, C1-30-alkyl, C2-30-alkenyl, C2-30-alkynyl, C5-12-cycloalkyl, C6-18-aryl, 5 to 20 membered hetero-aryl, OR21, OC(O)—R21, C(O)—OR21, C(O)—R21, NR21R22, NR21—C(O)R22, C(O)—NR21R22, N[C(O)R21][C(O)R22], SR21, halogen, CN, SiRSisRSitRSiu and OH, L1 and L2 are independently from each other and at each occurrence selected from the group consisting of C6-30-arylene, 5 to 30 membered heteroarylene.

  包含至少一个式 1 单元的聚合物和式 1′ 的化合物 其中，在式 1 和 1′ 中，n 为 0、1、2、3 或 4 m 为 0、1、2、3 或 4 X 在每次出现时均选自由 O、S、Se 或 Te 组成的组、Q 在每次出现时均选自由 C、Si 或 Ge 组成的组 R 在每次出现时均选自由氢、C1-30-烷基、C2-30-烯基、C2-30-炔基、C5-12-环烷基、C6-18-芳基、R2、R2′、R* 在每次出现时均独立地选自氢、C1-30-烷基、C2-30-烯基、C2-30-炔基、C5-12-环烷基、C6-18-芳基、5 至 20 个成员的杂芳基、OR21、OC(O)-R21、C(O)-OR21、C(O)-R21、NR21R22、NR21-C(O)R22、C(O)-NR21R22、N[C(O)R21][C(O)R22]、SR21、卤素、CN、SiRSisRSitRSiu 和 OH。