4,4,9,9-tetradodecyl-4,9-dihydro-s-indaceno-[1,2-b:5,6-b0]dithiophene | 1334054-35-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4,4,9,9-tetradodecyl-4,9-dihydro-s-indaceno-[1,2-b:5,6-b0]dithiophene
• 英文别名: 4,9-dihydro-4,4,9,9-tetradodecyl-indaceno[1,2-b:5,6-b']dithiophene；9,9,18,18-Tetradodecyl-5,14-dithiapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1(12),2,4(8),6,10,13(17),15-heptaene；9,9,18,18-tetradodecyl-5,14-dithiapentacyclo[10.6.0.03,10.04,8.013,17]octadeca-1(12),2,4(8),6,10,13(17),15-heptaene
• CAS: 1334054-35-1
• 化学式: C₆₄H₁₀₆S₂
• 分子量: 939.678
• InChiKey: KNVBLGFKQFXFAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  30.2
• 重原子数：
  66
• 可旋转键数：
  44
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4,9,9-tetradodecyl-4,9-dihydro-s-indaceno-[1,2-b:5,6-b0]dithiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以90%的产率得到2,7-dibromo-4,9-dihydro-4,4,9,9-tetradodecyl-indaceno[1,2-b:5,6-b']dithiophene
  参考文献：
  名称：

  具有可变侧链的基于茚并二噻吩核的小分子，用于溶液处理的整体异质结太阳能电池

  摘要：

  两个indacenodithiophene（IDT）基于核的小分子体积大的4-己基苯基和柔性的不同侧链Ñ具有相同数目的碳原子，即十二烷基SM1和SM2，分别设计并作为供体材料的有机太阳能合成单元（OSC）。深入研究了不同侧链结合IDT核对光吸收，电化学性能，空穴迁移率，薄膜形态和太阳能电池性能的影响。两种化合物在450-700 nm的波长范围内具有较宽的吸收率，相对较低的HOMO能级为-5.46和-5.52 eV。基于SM2作为供体材料的OSC的功率转换效率（PCE）和PC61 BM作为受体材料（1：2，w / w）为2.33％。相反，对于基于SM1作为施主和PC 71 BM作为受主（1：2，w / w）的装置，无需任何处理，例如热退火或利用溶剂添加剂，即可获得4.72％的PCE。

  DOI：

  10.1039/c3ta14659f
• 作为产物：
  描述：

  4,9-二氢--S-苯并二茚并[1,2-B:5,6-B']二噻吩(PM146) 、 溴代十二烷 在 sodium t-butanolate 作用下， 以 二甲基亚砜 为溶剂， 反应 9.0h， 以50%的产率得到4,4,9,9-tetradodecyl-4,9-dihydro-s-indaceno-[1,2-b:5,6-b0]dithiophene
  参考文献：
  名称：

  Synthesis and Photovoltaic Properties of D–A Copolymers Based on Alkyl-Substituted Indacenodithiophene Donor Unit

  摘要：

  Four D-A copolymers of tetradodecyl-substituted indacenodithiophene (IDT) donor unit with different acceptor units including bis(thiophen-2-yl)-bithiazole (BT2), bis(thiophen-2-yl)thiazolothiazole (TTz), bis(thiophen-2-yl)-tetrazine (TZ), and bis(thiophen-2-yl)-benzothiadiazole (DTBT), PIDT-BTz, PIDT-TTz, PIDT-TZ, and PIDT-DTBT, were synthesized for the application as donor materials in polymer solar cells (PSCs). The copolymers possess good solubility benefitted from the four alkyl side chains on IDT unit, deeper HOMO levels at ca. -5.2 eV thanks to the IDT unit and tunable bandgap depending on the acceptor units. Among the copolymers, PIDT-TTz has the highest hole mobility (mu(h)) of 4.99 x 10(-3) cm(2)/V s. The power conversion efficiency (PCE) of the PSC based on PIDT-TTz/PC70BM (1:2 w/w) reached 5.79%, under the illumination of AM1.5G, 100 mW/cm(2). PIDT-DTBT film has the smallest bandgap of 1.68 eV and a higher mu(h) of 2.24 x 10(-3) cm(2)/V s. The PSC based on PIDT-DTBT/PC70BM (1:3 w/w) exhibited an even higher PCE of 6.17% with a J(sc) of 13.27 mA/cm(2), a V., of 0.82 V-oc and a FF of 56.9%.

  DOI：

  10.1021/cm2019586

文献信息

• Synthesis and Photovoltaic Properties of D–A Copolymers Based on Alkyl-Substituted Indacenodithiophene Donor Unit
  作者：Maojie Zhang、Xia Guo、Xiaochen Wang、Haiqiao Wang、Yongfang Li

  DOI：10.1021/cm2019586

  日期：2011.9.27

  Four D-A copolymers of tetradodecyl-substituted indacenodithiophene (IDT) donor unit with different acceptor units including bis(thiophen-2-yl)-bithiazole (BT2), bis(thiophen-2-yl)thiazolothiazole (TTz), bis(thiophen-2-yl)-tetrazine (TZ), and bis(thiophen-2-yl)-benzothiadiazole (DTBT), PIDT-BTz, PIDT-TTz, PIDT-TZ, and PIDT-DTBT, were synthesized for the application as donor materials in polymer solar cells (PSCs). The copolymers possess good solubility benefitted from the four alkyl side chains on IDT unit, deeper HOMO levels at ca. -5.2 eV thanks to the IDT unit and tunable bandgap depending on the acceptor units. Among the copolymers, PIDT-TTz has the highest hole mobility (mu(h)) of 4.99 x 10(-3) cm(2)/V s. The power conversion efficiency (PCE) of the PSC based on PIDT-TTz/PC70BM (1:2 w/w) reached 5.79%, under the illumination of AM1.5G, 100 mW/cm(2). PIDT-DTBT film has the smallest bandgap of 1.68 eV and a higher mu(h) of 2.24 x 10(-3) cm(2)/V s. The PSC based on PIDT-DTBT/PC70BM (1:3 w/w) exhibited an even higher PCE of 6.17% with a J(sc) of 13.27 mA/cm(2), a V., of 0.82 V-oc and a FF of 56.9%.
• Indacenodithiophene core-based small molecules with tunable side chains for solution-processed bulk heterojunction solar cells
  作者：Xin Liu、QingDuan Li、Yunchuan Li、Xiong Gong、Shi-Jian Su、Yong Cao

  DOI：10.1039/c3ta14659f

  日期：——

  different side chains of bulky 4-hexylphenyl and flexible n-dodecyl with the same number of carbon atom, namely SM1 and SM2, respectively, were designed and synthesized as the donor materials in organic solar cells (OSCs). The impacts of the different side chains combined with the IDT core on the optical absorption, electrochemical property, hole mobility, film morphology, and solar cell performance

  两个indacenodithiophene（IDT）基于核的小分子体积大的4-己基苯基和柔性的不同侧链Ñ具有相同数目的碳原子，即十二烷基SM1和SM2，分别设计并作为供体材料的有机太阳能合成单元（OSC）。深入研究了不同侧链结合IDT核对光吸收，电化学性能，空穴迁移率，薄膜形态和太阳能电池性能的影响。两种化合物在450-700 nm的波长范围内具有较宽的吸收率，相对较低的HOMO能级为-5.46和-5.52 eV。基于SM2作为供体材料的OSC的功率转换效率（PCE）和PC61 BM作为受体材料（1：2，w / w）为2.33％。相反，对于基于SM1作为施主和PC 71 BM作为受主（1：2，w / w）的装置，无需任何处理，例如热退火或利用溶剂添加剂，即可获得4.72％的PCE。