tetrabromo-Δ4,4'-dicyclopenta[2,1-b:3,4-b']dithiophene | 1257842-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: tetrabromo-Δ4,4'-dicyclopenta[2,1-b:3,4-b']dithiophene
• CAS: 1257842-63-9
• 化学式: C₁₈H₄Br₄S₄
• 分子量: 668.11
• InChiKey: XRTVCNTUNJBOGC-UHFFFAOYSA-N

物化性质

• 沸点：
  656.4±55.0 °C(Predicted)
• 密度：
  2.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.95
• 重原子数：
  26.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tetrabromo-Δ4,4'-dicyclopenta[2,1-b:3,4-b']dithiophene 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 72.67h， 生成 tetrakis(5'-bromo-2'-thienyl)-Δ4,4'-dicyclopenta[2,1-b:3,4-b']dithiophene
  参考文献：
  名称：

  H-Shaped Oligothiophenes with Low Band Gaps and Amphoteric Redox Properties

  摘要：

  H-shaped bridged oligothiophenes HT-1 and HT-2 were synthesized by two different approaches. Different from normal oligothiophenes, HT-1 and HT-2 showed low band gaps and amphoteric redox behaviors due to intramolecular charge transfer, which is further supported by time-dependent Dr calculations.

  DOI：

  10.1021/ol102456c
• 作为产物：
  描述：

  Δ^4,4′-Dicyclopenta[2,1-b:3,4-b′]dithiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到tetrabromo-Δ4,4'-dicyclopenta[2,1-b:3,4-b']dithiophene
  参考文献：
  名称：

  H-Shaped Oligothiophenes with Low Band Gaps and Amphoteric Redox Properties

  摘要：

  H-shaped bridged oligothiophenes HT-1 and HT-2 were synthesized by two different approaches. Different from normal oligothiophenes, HT-1 and HT-2 showed low band gaps and amphoteric redox behaviors due to intramolecular charge transfer, which is further supported by time-dependent Dr calculations.

  DOI：

  10.1021/ol102456c

文献信息

• Fluorinated Pentafulvalene‐Fused Hole‐Transporting Material Enhances the Performance of Perovskite Solar Cells with Efficiency Exceeding 23%
  作者：Kun‐Mu Lee、Yao‐Shen Huang、Wei‐Hao Chiu、Ying‐Kai Huang、Gao Chen、Gizachew Belay Adugna、Sie‐Rong Li、Fang‐Ju Lin、Shih‐I. Lu、Hsiao‐Chi Hsieh、Kang‐Ling Liau、Chun‐Cheng Huang、Yian Tai、Yu‐Tai Tao、Yan‐Duo Lin

  DOI：10.1002/adfm.202306367

  日期：2023.11

  Organic small molecular materials with coplanar π‐conjugated system as HTMs in perovskite solar cells (PSCs) have attracted considerable attention due to their high charge transport capability and thermal stability. Herein, three novel pentafulvalene‐fused derivatives with or without fluorine atoms incorporated (YSH‐oF and YSH‐mF and YSH‐H, respectively) are designed, synthesized, and applied as hole‐transporting materials (HTMs) in PSCs fabrication. The fluorinated HTMs, YSH‐oF and YSH‐mF, exhibited higher hole mobility and better charge extraction at the perovskite/HTM interface than non‐fluorinated one do, presumably due to the closer intermolecular π–π packing interactions. As a result, small‐area (0.09 cm²) PSCs made with YSH‐oF and YSH‐mF achieved an impressive power conversion efficiency (PCE) of 23.59% and 22.76% respectively, with negligible hysteresis, in contrast with the 20.57% for the YSH‐H‐based devices. Furthermore, for large‐area (1.00 cm²) devices, the PSCs employing YSH‐oF exhibited a PCE of 21.92%. Moreover, excellent long‐term device stability is demonstrated for PSCs with F‐substituted HTMs (YSH‐oF and YSH‐mF), presumably due to the higher hydrophobicity. This study shows the great potential of fluorinated pentafulvalene‐fused materials as low‐cost HTM for efficient and stable PSCs.

  摘要 具有共面π共轭体系的有机小分子材料作为过氧化物太阳能电池（PSCs）中的HTMs，因其高电荷传输能力和热稳定性而备受关注。本文设计、合成了三种新颖的含或不含氟原子的五聚戊烯衍生物（分别为 YSH-oF 和 YSH-mF 及 YSH-H），并将其作为空穴传输材料（HTMs）应用于 PSCs 的制造。氟化 HTM（YSH-oF 和 YSH-mF）与非氟化 HTM 相比，在过氧化物/HTM 界面表现出更高的空穴迁移率和更好的电荷萃取，这可能是由于分子间的π-π堆积相互作用更紧密所致。因此，使用 YSH-oF 和 YSH-mF 制成的小面积（0.09 cm2）PSCs 实现了令人印象深刻的功率转换效率（PCE），分别为 23.59% 和 22.76%，滞后几乎可以忽略不计，而基于 YSH-H 的器件的功率转换效率仅为 20.57%。此外，对于大面积（1.00 平方厘米）器件，采用 YSH-oF 的 PSC 的 PCE 为 21.92%。此外，使用 F 取代 HTM（YSH-oF 和 YSH-mF）的 PSC 具有出色的长期器件稳定性，这可能是由于其疏水度较高。这项研究表明，含氟五聚戊烯融合材料作为低成本 HTM，在高效、稳定的 PSC 方面具有巨大潜力。