1-(5-bromothiophen-2-yl)-5-octyl-3-(thiophen-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione | 1603829-50-0

• 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: 1-(5-bromothiophen-2-yl)-5-octyl-3-(thiophen-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• 英文别名: 3-(5-Bromothiophen-2-yl)-5-octyl-1-thiophen-2-ylthieno[3,4-c]pyrrole-4,6-dione；3-(5-bromothiophen-2-yl)-5-octyl-1-thiophen-2-ylthieno[3,4-c]pyrrole-4,6-dione
• CAS: 1603829-50-0
• 化学式: C₂₂H₂₂BrNO₂S₃
• 分子量: 508.524
• InChiKey: BZGAUHLKEACOLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4,8-双((2-乙基己基)氧基)苯并[1,2-b:4,5-b]二噻吩-2,6-二基)双(三甲基锡) 、 1-(5-bromothiophen-2-yl)-5-octyl-3-(thiophen-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以46%的产率得到3-[5-[4,8-Bis(2-ethylhexoxy)-2-[5-(5-octyl-4,6-dioxo-1-thiophen-2-ylthieno[3,4-c]pyrrol-3-yl)thiophen-2-yl]thieno[2,3-f][1]benzothiol-6-yl]thiophen-2-yl]-5-octyl-1-thiophen-2-ylthieno[3,4-c]pyrrole-4,6-dione
  参考文献：
  名称：

  유기 반도체 화합물, 이의 제조방법 및 이를 채용한 유기 태양전지

  摘要：

  本发明涉及由单分子有机半导体化合物制成的有机太阳能电池，以及其制造方法和采用该化合物的有机太阳能电池。更具体地说，本发明涉及引入芳香族化合物和含有亚胺基的区域的分子内电子受体的单分子有机半导体化合物，其制造方法，含有这种单分子有机半导体化合物的高分子化合物，以及含有高分子化合物的有机太阳能电池。

  公开号：

  KR101563120B1
• 作为产物：
  描述：

  N-正辛基-3,4-噻吩二甲酰亚胺 在 N-溴代丁二酰亚胺(NBS) 、 trans-bis(triphenylphosphine)palladium dichloride 、 硫酸 、 三氟乙酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.0h， 生成 1-(5-bromothiophen-2-yl)-5-octyl-3-(thiophen-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
  参考文献：
  名称：

  Thieno[3,4-c]pyrrole-4,6-dione-Based Small Molecules for Highly Efficient Solution-Processed Organic Solar Cells

  摘要：

  AbstractTwo small molecules named BT‐TPD and TBDT‐TTPD with a thieno[3,4‐c]pyrrole‐4,6‐dione (TPD) unit were designed and synthesized for solution‐processed bulk‐heterojunction solar cells. Their thermal, electrochemical, optical, charge‐transport, and photovoltaic characteristics were investigated. These compounds exhibit strong absorption at 460–560 nm and low highest occupied molecular orbital levels (−5.36 eV). Field‐effect hole mobilities of these compounds are 1.7–7.7×10−3 cm2 V−1 s−1. Small‐molecule organic solar cells based on blends of these donor molecules and a acceptor display power conversion efficiencies as high as 4.62 % under the illumination of AM 1.5G, 100 mW cm−2.

  DOI：

  10.1002/asia.201301357

文献信息

• DTBDT-TTPD: a new dithienobenzodithiophene-based small molecule for use in efficient photovoltaic devices
  作者：Ye Rim Cheon、Yu Jin Kim、Jang Yeol Back、Tae kyu An、Chan Eon Park、Yun-Hi Kim

  DOI：10.1039/c4ta03745f

  日期：——

  We designed and synthesized a dithienobenzodithiophene-based molecule with a planar molecular geometry, DTBDT-TTPD. It showed low band gap, deep HOMO level and the photovoltaic characteristics included a power conversion efficiency as high as 4.48%.

  我们设计并合成了一种基于二噁嘧吩的分子，具有平面分子几何结构，DTBDT-TTPD。它表现出较低的带隙、深的HOMO能级，光伏特性包括高达4.48%的功率转换效率。
• 벤조다이사이에노사이오펜 유도체 및 이를 채용하고 있는 유기태양전지
  申请人：INDUSTRY-ACADEMIC COOPERATION FOUNDATION GYEONGSANG NATIONAL UNIVERSITY 경상국립대학교산학협력단(220040107194) BRN ▼613-82-11653

  公开号：KR101602727B1

  公开（公告）日：2016-03-14

  본 발명은 벤조다이사이에노사이오펜 유도체 및 이를 채용하고 있는 유기태양전지에 관한 것이다. 본 발명의 벤조다이사이에노사이오펜 유도체는 분자 내 전자 주게인 벤조다이사이에노사이오펜과 전자 받게인 알킬기를 동시에 가지는 화합물로, 높은 용해성을 가지며, 이를 활성층 재료로 채용한 유기태양전지는 우수한 산화안정성, 높은 개방 전압값 및 전류밀도를 가진다.

  这项发明涉及苯并二嗪并硫代苯并二嗪衍生物及其在有机太阳能电池中的应用。该发明的苯并二嗪并硫代苯并二嗪衍生物是一种具有分子内电子供体苯并二嗪并电子受体烷基的化合物，具有高溶解性。采用该化合物作为活性层材料的有机太阳能电池具有优异的氧化稳定性、高开路电压和电流密度。
• A high-performance solution-processed small molecule: alkylselenophene-substituted benzodithiophene organic solar cell
  作者：Yu Jin Kim、Jang Yeol Baek、Jong-jin Ha、Dae Sung Chung、Soon-Ki Kwon、Chan Eon Park、Yun-Hi Kim

  DOI：10.1039/c4tc00187g

  日期：——

  A solution-processed alkylselenophene-substituted benzodithiophene (BDT) small molecule, namely, 3,3′-((4,8-bis(5-(2-ethylhexyl)selenophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl)bis(thiophene-5,2-diyl))bis(5-octyl-1-(thiophen-2-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione) (BDTSe-TTPD), with broad absorption and suitable energy levels was synthesized. The widely used solvents o-dichlorobenzene (o-DCB)

  溶液处理的烷基硒烯取代的苯并二噻吩（BDT）小分子，即3,3'-（（4,8-双（5-（2-乙基己基）硒代吩-2-基）苯并[1,2- b]： 4,5 - b '] dithiophene-2,6-diyl）bis（thiophene-5,2-diyl））bis（5-octyl-1-（thiophen-2-yl）-4 H -thieno [3,4 - c ^ ]吡咯-4,6（5 ħ） -二酮）（BDTSe-TTPD），具有宽的吸收和合适的能量水平的合成。广泛使用的溶剂邻二氯苯（o -DCB），氯苯（CB）或氯仿（CF）作为旋涂溶剂，以BDTSe-TTPD作为施主材料和PC 71来制造高效的光伏器件。BM为受体。与由o -DCB和CB解决方案制造的设备相比，由CF解决方案制造的设备在短路电流，填充因子和功率转换效率方面表现出更好的性能。最后，通过优化有源层的厚度，在100 mW cm -2的模拟AM
• [EN] BENZODITHIENOTHIOPHENE DERIVATIVE AND ORGANIC SOLAR CELL USING SAME<br/>[FR] DÉRIVÉ DE BENZODITHIÉNOTHIOPHÈNE ET CELLULE SOLAIRE ORGANIQUE L'UTILISANT<br/>[KO] 벤조다이사이에노사이오펜 유도체 및 이를 채용하고 있는 유기태양전지
  申请人：NAT UNIV GYEONGSANG IACF

  公开号：WO2015194703A1

  公开（公告）日：2015-12-23

  본 발명은 벤조다이사이에노사이오펜 유도체 및 이를 채용하고 있는 유기태양전지에 관한 것이다. 본 발명의 벤조다이사이에노사이오펜 유도체는 분자 내 전자 주게인 벤조다이사이에노사이오펜과 전자 받게인 알킬기를 동시에 가지는 화합물로, 높은 용해성을 가지며, 이를 활성층 재료로 채용한 유기태양전지는 우수한 산화안정성, 높은 개방 전압값 및 전류밀도를 가진다.
• Thieno[3,4-<i>c</i>]pyrrole-4,6-dione-Based Small Molecules for Highly Efficient Solution-Processed Organic Solar Cells
  作者：Jong-jin Ha、Yu Jin Kim、Jong-gwang Park、Tae Kyu An、Soon-Ki Kwon、Chan Eon Park、Yun-Hi Kim

  DOI：10.1002/asia.201301357

  日期：2014.4

  AbstractTwo small molecules named BT‐TPD and TBDT‐TTPD with a thieno[3,4‐c]pyrrole‐4,6‐dione (TPD) unit were designed and synthesized for solution‐processed bulk‐heterojunction solar cells. Their thermal, electrochemical, optical, charge‐transport, and photovoltaic characteristics were investigated. These compounds exhibit strong absorption at 460–560 nm and low highest occupied molecular orbital levels (−5.36 eV). Field‐effect hole mobilities of these compounds are 1.7–7.7×10−3 cm2 V−1 s−1. Small‐molecule organic solar cells based on blends of these donor molecules and a acceptor display power conversion efficiencies as high as 4.62 % under the illumination of AM 1.5G, 100 mW cm−2.