4-(4,4-bis(2-ethylhexyl)-6-(trimethylstannyl)-4H-silolo[3,2-b:4,5-b']dithiophen-2-yl)-7-(5'-hexyl-[2,2'-bithiophen]-5-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine | 1361033-98-8

• 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
• 英文名称: 4-(4,4-bis(2-ethylhexyl)-6-(trimethylstannyl)-4H-silolo[3,2-b:4,5-b']dithiophen-2-yl)-7-(5'-hexyl-[2,2'-bithiophen]-5-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine
• 英文别名: 5-{(4-(7-hexylthiophen-2-yl)thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine}-5'-{trimethylstannyl}-3,3'-bis(2-ethylhexyl)silylene-2,2'-bithiophene
• CAS: 1361033-98-8
• 化学式: C₄₆H₆₃N₃S₅SiSn
• 分子量: 965.152
• InChiKey: CHBJMHQWZKZPMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.98
• 重原子数：
  56.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.67
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4,7-二溴-[1,2,5]噻二唑并[3,4-c]吡啶 、 4-(4,4-bis(2-ethylhexyl)-6-(trimethylstannyl)-4H-silolo[3,2-b:4,5-b']dithiophen-2-yl)-7-(5'-hexyl-[2,2'-bithiophen]-5-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 0.82h， 以56%的产率得到
  参考文献：
  名称：

  Design and Properties of Intermediate-Sized Narrow Band-Gap Conjugated Molecules Relevant to Solution-Processed Organic Solar Cells

  摘要：

  Increases in the molecular length of narrow band gap conjugated chromophores reveal potentially beneficial optical and electronic properties, thermal stabilities, and high power conversion efficiencies when integrated into optoelectronic devices, such as bulk heterojunction organic solar cells. With the objective of providing useful information for understanding the transition from small-sized molecules to polymers, as well as providing a general chemical design platform for extracting relationships between molecular structure and bulk properties, we set out to vary the electron affinity of the molecular backbone. Therefore, a series of donor (D) acceptor (A) alternating narrow band gap conjugated chromophores were synthesized based on the general molecular frameworks: D-1-A(1)-D-2-A(2)-D-2-A(1)-D-1 and D-1-A(1)-D-2-A(2)-D-2-A(2)-D-2-A(1)-D-1. When the central electron-accepting moiety (A(2)) was varied or modified, two classes of molecules could be compared. First, we showed that the alteration of one single electron-accepting group, while maintaining the shape of the molecular framework, can effectively impact the optical properties and energy levels of the molecules. DFT ground state structure optimizations show similar "U" shape conformations among these molecules. Second, we examined how the site-specific introduction of fluorine atom(s) modifies the thermal properties in the solid state, while maintaining relatively similar optical and electrochemical features of interest. Structure property relationship of such molecular systems could be rationally evaluated in the aspects of thermal-responsive molecular organizations in the solid state and dipole moments both in the ground and excited states. The impact of molecular structure on charge carrier mobilities in field effect transistors and the performance of photovoltaic devices were also studied.

  DOI：

  10.1021/ja413144u
• 作为产物：
  描述：

  4,4-二-2-乙基己基-二硫代[3,2-b：2'，3'-d]甲硅烷基 在 四(三苯基膦)钯 、 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 8.65h， 生成 4-(4,4-bis(2-ethylhexyl)-6-(trimethylstannyl)-4H-silolo[3,2-b:4,5-b']dithiophen-2-yl)-7-(5'-hexyl-[2,2'-bithiophen]-5-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine
  参考文献：
  名称：

  Narrow-Band-Gap Conjugated Chromophores with Extended Molecular Lengths

  摘要：

  The influence of extending the molecular length of donor acceptor chromophores on properties relevant to organic optoelectronic devices has been studied by using two new narrow-band-gap systems. Most significantly, we find that the higher molecular weight systems exhibit higher thermal stabilities (beyond 200 degrees C) when introduced into field effect transistor devices. It is also possible to fabricate bulk heterojunction solar cells using PC61BM with power conversion efficiencies >6%. These high values are not heavily influenced by the blend composition and are achieved without the influence of solvent additives or postdeposition thermal annealing.

  DOI：

  10.1021/ja310483w

文献信息

• Pyridalthiadiazole-Based Narrow Band Gap Chromophores
  作者：Zachary B. Henson、Gregory C. Welch、Thomas van der Poll、Guillermo C. Bazan

  DOI：10.1021/ja209331y

  日期：2012.2.29

  levels both in solution and in the bulk. Substitution of different alkyl chains on D(2) gives rise to controllable melting and crystallization temperatures and tailored solubility. Alterations to the core donor D(2) lead to readily identifiable changes in all properties studied. Finally, the regiochemistry of the pyridal N-atom in the PT heterocycle was investigated. The tailoring of structures via subtle

  含有吡啶并 [2,1,3] 噻二唑 (PT) 单元的 π 共轭材料最近在溶液处理的分子本体异质结 (BHJ) 有机光伏器件中实现了 6.7% 的创纪录功率转换效率。认识到这类新分子系统的重要性，并为了建立更具体的路径来预测所需固态特性的改进，我们着手系统地改变分子框架并评估结构-性能关系。因此，提供了 13 种结构相关的 D(1)-PT-D(2)-PT-D(1) 化合物的合成和性质，其中 D 表示与 PT 相比相对富电子的芳香链段。使用吸收光谱、循环伏安法、热重分析、差示扫描量热法和溶解度分析。对封端 D(1) 单元的更改允许对溶液中和本体中的电子能级进行精细控制。D(2) 上不同烷基链的取代产生可控的熔化和结晶温度以及定制的溶解度。对核心供体 D(2) 的改变导致所有研究性质的容易识别的变化。最后，研究了 PT 杂环中吡啶 N 原子的区域化学。通过所呈现的分子系列中的细微结构修改来定制结
• Intermediate-Sized Conjugated Donor Molecules for Organic Solar Cells: Comparison of Benzodithiophene and Benzobisthiazole-Based Cores
  作者：Siyuan Zhang、Junxiang Zhang、Maged Abdelsamie、Qinqin Shi、Yadong Zhang、Timothy C. Parker、Evgheni V. Jucov、Tatiana V. Timofeeva、Aram Amassian、Guillermo C. Bazan、Simon B. Blakey、Stephen Barlow、Seth R. Marder

  DOI：10.1021/acs.chemmater.7b02665

  日期：2017.9.26

  Two intermediate-sized donor molecules, BBTz-X and BDT-X, have been synthesized by the Stille coupling between 4-(4,4-bis(2-ethylhexyl)-6-(trimethylstannyl)-4H-silolo[3,2-b:4,5-b′]dithiophen-2-yl)-7-(5′-hexyl-[2,2′-bithiophen]-5-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine and either 4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-2,6-diiodobenzo[1,2-d:4,5-d′]bis(thiazole) or 2,6-dibromo-4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene, respectively. Both oxidation and reduction potentials for BBTz-X are anodically shifted relative to those for BDT-X, but the oxidation potential is more sensitive to the identity of the core; this is consistent with what is seen for DFT-calculated HOMO and LUMO energies and with a slightly blue-shifted absorption maximum for BBTz-X. Although DFT calculations, along with crystal structures of related compounds, suggest more planar molecular structures for BBTz-X than for BDT-X, film structures and the effects of various annealing processes on these films, as revealed by GIWAXS, are similar. The performance of BDT-X:PC61BM bulk-heterojunction solar cells is more sensitive to annealing conditions than that of BBTz-X:PC61BM cells, but under appropriate conditions, both yield power conversion efficiencies of >7%.

  通过在4-(4,4-双(2-乙基己基)-6-(三甲基锡烷基)-4H-硅咯并[3,2-b:4,5-b′]二噻吩-2-基)-7-(5′-己基-[2,2′-联噻吩]-5-基)-[1,2,5]噻二唑并[3,4-c]吡啶与4,8-双(5-(2-乙基己基)噻吩-2-基)-2,6-二碘苯并[1,2-d:4,5-d′]双(噻唑)或2,6-二溴-4,8-双(5-(2-乙基己基)噻吩-2-基)苯并[1,2-b:4,5-b′]二噻吩之间进行斯蒂尔偶联，分别合成了两个中等大小的供体分子BBTz-X和BDT-X。BBTz-X的氧化和还原电位相对于BDT-X的氧化和还原电位而言，在阳极发生了偏移，但氧化电位对核心的识别更为敏感；这与DFT计算的HOMO和LUMO能量以及BBTz-X的吸收最大值