5,5,11,11-tetrakis(4-octyloxyphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene | 1411976-71-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 5,5,11,11-tetrakis(4-octyloxyphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene
• 英文别名: 12,12,24,24-Tetrakis(4-octoxyphenyl)-5,9,17,21-tetrathiaheptacyclo[13.9.0.03,13.04,11.06,10.016,23.018,22]tetracosa-1(15),2,4(11),6(10),7,13,16(23),18(22),19-nonaene；12,12,24,24-tetrakis(4-octoxyphenyl)-5,9,17,21-tetrathiaheptacyclo[13.9.0.03,13.04,11.06,10.016,23.018,22]tetracosa-1(15),2,4(11),6(10),7,13,16(23),18(22),19-nonaene
• CAS: 1411976-71-0
• 化学式: C₇₆H₉₀O₄S₄
• 分子量: 1195.81
• InChiKey: DTDIWUFIRUNNNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26.6
• 重原子数：
  84
• 可旋转键数：
  36
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,5,11,11-tetrakis(4-octyloxyphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 16.0h， 以59%的产率得到3,9-dibromo-5,5,11,11-tetrakis(4-octyloxyphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene
  参考文献：
  名称：

  [EN] ORGANIC SEMICONDUCTORS
  [FR] SEMI-CONDUCTEURS ORGANIQUES

  摘要：

  公开号：

  WO2013010614A3
• 作为产物：
  描述：

  在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以81%的产率得到5,5,11,11-tetrakis(4-octyloxyphenyl)-dithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene
  参考文献：
  名称：

  Synthesis, Molecular and Photovoltaic Properties of Donor–Acceptor Conjugated Polymers Incorporating a New Heptacylic Indacenodithieno[3,2-b]thiophene Arene

  摘要：

  We have developed a new multifused indacenodithieno[3,2-b]thiophene arene (IDTT) unit where the central phenylene is covalently fastened with the two outer thieno[3,2-b]thiophene (TT) rings, forming two cyclopentadiene rings embedded in a heptacyclic structure. This rigid and coplanar IDTT building block was copolymerized with electron-deficient acceptors, 4,7-dibromo-2,1,3-benzothiadiazole (BT), 4,7-dibromo-5,6-difluoro-2,1,3-benzothiadiazole (FBT) and 1,3-dibromo-thieno[3,4-c]pyrrole-4,6-dione (TPD) via Stifle polymerization, respectively. Because the higher content of the thienothiophene moieties in the fully coplanar IDTT structure facilitates pi-electron delocalization, these new polymers show much improved light-harvesting abilities and enhanced charge mobilities compared to PDITTBT copolymer using hexacyclic diindenothieno[3,2-b]thiophene (DITT) as the donor moieties. The device using PIDTTBT:PC71BM (1:4, w/w) exhibited a decent power conversion efficiency (PCE) of 3.8%. Meanwhile, the solar cell using PIDTTFBT:PC71BM (1:4 in wt %) blend exhibited a greater V-oc value of 0.9 V and a larger J(sc) of 10.08 mA/cm(2), improving the PCE to 4.2%. The enhanced V-oc is attributed to the lower-lying of HOMO energy level of PIDTTFBT as a result of fluorine withdrawing effect on the BT unit. A highest PCE of 4.3% was achieved for the device incorporating PIDTTTPD:PC71BM (1:4 in wt %) blend.

  DOI：

  10.1021/ma3019552

文献信息

• 인다세노-디티에노티오펜 화합물을 합성하는 제조 방법
  申请人：CMDL Co.,Ltd. (주)씨엠디엘(120170170502) Corp. No ▼ 161511-0210660BRN ▼171-81-00621

  公开号：KR20190113044A

  公开（公告）日：2019-10-08

  신규한 출발 물질로서, 비스(티에노[3,2-b]티오펜-2-일)-비스메타논 유도체를 이용하여 인다세노-디티에노티오펜 화합물을 합성하는 제조 방법을 제공한다.

  作为一种新的起始物质，提供了一种使用双(噻吩[3,2-b]噻吩-2-基)-双甲酮衍生物合成印地诺-二噻吩噻吩化合物的制备方法。
• [EN] ORGANIC SEMICONDUCTORS<br/>[FR] SEMI-CONDUCTEURS ORGANIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2013010614A3

  公开（公告）日：2013-06-20
• Synthesis, Molecular and Photovoltaic Properties of Donor–Acceptor Conjugated Polymers Incorporating a New Heptacylic Indacenodithieno[3,2-<i>b</i>]thiophene Arene
  作者：Huan-Hsuan Chang、Che-En Tsai、Yu-Ying Lai、De-Yang Chiou、So-Lin Hsu、Chain-Shu Hsu、Yen-Ju Cheng

  DOI：10.1021/ma3019552

  日期：2012.12.11

  We have developed a new multifused indacenodithieno[3,2-b]thiophene arene (IDTT) unit where the central phenylene is covalently fastened with the two outer thieno[3,2-b]thiophene (TT) rings, forming two cyclopentadiene rings embedded in a heptacyclic structure. This rigid and coplanar IDTT building block was copolymerized with electron-deficient acceptors, 4,7-dibromo-2,1,3-benzothiadiazole (BT), 4,7-dibromo-5,6-difluoro-2,1,3-benzothiadiazole (FBT) and 1,3-dibromo-thieno[3,4-c]pyrrole-4,6-dione (TPD) via Stifle polymerization, respectively. Because the higher content of the thienothiophene moieties in the fully coplanar IDTT structure facilitates pi-electron delocalization, these new polymers show much improved light-harvesting abilities and enhanced charge mobilities compared to PDITTBT copolymer using hexacyclic diindenothieno[3,2-b]thiophene (DITT) as the donor moieties. The device using PIDTTBT:PC71BM (1:4, w/w) exhibited a decent power conversion efficiency (PCE) of 3.8%. Meanwhile, the solar cell using PIDTTFBT:PC71BM (1:4 in wt %) blend exhibited a greater V-oc value of 0.9 V and a larger J(sc) of 10.08 mA/cm(2), improving the PCE to 4.2%. The enhanced V-oc is attributed to the lower-lying of HOMO energy level of PIDTTFBT as a result of fluorine withdrawing effect on the BT unit. A highest PCE of 4.3% was achieved for the device incorporating PIDTTTPD:PC71BM (1:4 in wt %) blend.