4-(2-ethylhexyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde | 1346644-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 英文名称: 4-(2-ethylhexyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde
• 英文别名: 7-(2-Ethylhexyl)-3,11-dithia-7-azatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene-4-carbaldehyde；7-(2-ethylhexyl)-3,11-dithia-7-azatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene-4-carbaldehyde
• CAS: 1346644-03-8
• 化学式: C₁₇H₂₁NOS₂
• 分子量: 319.492
• InChiKey: SSRMJWIYFJAAIG-UHFFFAOYSA-N

物化性质

• 沸点：
  419.8±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-ethylhexyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到6-bromo-4-(2-ethylhexyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde
  参考文献：
  名称：

  基于双噻吩并[3,2- b：2'，3'- d ]吡咯的，可吸收NIR的溶液可加工小分子供体，用于高效的整体异质结太阳能电池†

  摘要：

  一种新型的，可吸收近红外光的有机小分子供体材料，称为ICT3，具有A–D–D–D–A结构，其中双噻吩并[3,2- b：2'，3'- d ]吡咯（DTP）和丁基若丹宁为供体分别合成了受体部分和受体部分，并研究了其热，光物理，电化学和光伏性质。ICT3在372°C的分解温度（T d相当于重量损失5％）的广泛温度范围内具有出色的稳定性，可溶于最常见的有机溶剂（溶解度最高30 mg mL -1），适用于溶液加工在器件制造过程中。ICT3已经广泛的（520-820纳米）和强烈的可见区域中的吸收（摩尔激发系数为1.69×10 5摩尔-1厘米-1），并具有合适的HOMO和LUMO能级与[6,6] -苯基-C 71 -丁酸甲酯（PC 71 BM）受体，可进行有效的激子离解和电荷转移。具有氧化铟锡（ITO）/聚（3,4-乙撑二氧噻吩）：聚苯乙烯磺酸盐（PEDOT：PSS）/ ICT3：PC 71 BM / poly（9

  DOI：

  10.1039/c6cp06304g
• 作为产物：
  描述：

  3,3'-二溴-2,2'-联噻吩 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 4-(2-ethylhexyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2-carbaldehyde
  参考文献：
  名称：

  基于双噻吩并[3,2- b：2'，3'- d ]吡咯的，可吸收NIR的溶液可加工小分子供体，用于高效的整体异质结太阳能电池†

  摘要：

  一种新型的，可吸收近红外光的有机小分子供体材料，称为ICT3，具有A–D–D–D–A结构，其中双噻吩并[3,2- b：2'，3'- d ]吡咯（DTP）和丁基若丹宁为供体分别合成了受体部分和受体部分，并研究了其热，光物理，电化学和光伏性质。ICT3在372°C的分解温度（T d相当于重量损失5％）的广泛温度范围内具有出色的稳定性，可溶于最常见的有机溶剂（溶解度最高30 mg mL -1），适用于溶液加工在器件制造过程中。ICT3已经广泛的（520-820纳米）和强烈的可见区域中的吸收（摩尔激发系数为1.69×10 5摩尔-1厘米-1），并具有合适的HOMO和LUMO能级与[6,6] -苯基-C 71 -丁酸甲酯（PC 71 BM）受体，可进行有效的激子离解和电荷转移。具有氧化铟锡（ITO）/聚（3,4-乙撑二氧噻吩）：聚苯乙烯磺酸盐（PEDOT：PSS）/ ICT3：PC 71 BM / poly（9

  DOI：

  10.1039/c6cp06304g

文献信息

• [EN] IMPROVED OLIGOTHIOPHENES<br/>[FR] OLIGOTHIOPHÈNES AMÉLIORÉS
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2011137487A1

  公开（公告）日：2011-11-10

  Compounds of Formula (I), wherein T is independently selected from the group consisting of (a). And the variables R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar, L and n are as defined in the specification herein. The compounds are capable of charge transportation and have application in organic photovoltaic devices such as dye sensitised solar cells.

  式（I）的化合物，其中T是从（a）组成的群体中独立选择的。变量R1、R2、R3、R4、R5、R6、R7、R8、R9、Ar、L和n的定义如本说明书中所述。这些化合物能够进行电荷传输，并在有机光伏器件中应用，例如染料敏化太阳能电池。
• OLIGOTHIOPHENES
  申请人：Evans Richard

  公开号：US20130042918A1

  公开（公告）日：2013-02-21

  Compounds of Formula (I): Wherein: R 1 and R 2 are independently selected from the group consisting of optionally substituted C 1 -C 20 alkyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted aromatic, and optionally substituted heteroaromatic groups or R 1 and R 2 together with the nitrogen atom to which they are attached comprise an optionally substituted saturated or unsaturated ring which may optionally contain further heteroatoms selected from the group consisting of O, N and S, and may optionally be further fused to one or more other rings; Ar is selected from the group consisting of optionally substituted aromatic and optionally substituted heteroaromatic groups; L is a linker which is a direct bond or is selected from the group consisting of optionally substituted C 2 alkenylene and optionally substituted C 2 alkynylene; T is independently selected from the group consisting of: R 3 , R 4 and R 9 are independently selected from the group consisting of hydrogen, optionally substituted C 1 -C 10 alkyl, optionally substituted C 3 -C 8 cycloalkyl and optionally substituted C 1 -C 10 alkoxy groups, or a pair of groups selected from R 3 , R 4 and R 9 may together with the carbon atoms to which they are attached comprise an optionally substituted saturated or unsaturated ring which may optionally contain one or more heteroatoms selected from the group consisting of O, N and S, and may optionally be further fused to one or more other rings; R 5 is selected from the group consisting of hydrogen, optionally substituted C 1 -C 8 alkyl, optionally substituted C 3 -C 8 cycloalkyl, and optionally substituted aromatic groups; R 6 is selected from the group consisting of optionally substituted C 1 -C 8 alkyl, optionally substituted C 1 -C 8 perfluorinated alkyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted aromatic, and optionally substituted heteroaromatic groups; R 7 is selected from the group consisting of optionally substituted C 1 -C 30 alkyl wherein one or more carbon atoms of the alkyl are optionally replaced with one or more of O, S, NR 8 , carbonyl or thiocarbonyl; optionally substituted C 3 -C 8 cycloalkyl; optionally substituted C 2 -C 12 alkenyl wherein one or more carbon atoms of the alkenyl are optionally replaced with one or more of O, S, NR 8 , carbonyl or thiocarbonyl; optionally substituted C 2 -C 8 alkynyl wherein one or more carbon atoms of the alkynyl are optionally replaced with one or more of O, S, NR 8 , carbonyl or thiocarbonyl; optionally substituted C 3 -C 12 alkoxy; optionally substituted aromatic; and optionally substituted heteroaromatic groups; wherein R 8 is hydrogen or R 6 , and n is an integer of 1 to 10. The compounds are capable of charge transportation and have application in organic photovoltaic devices such as dye sensitised solar cells.

  分子式(I)的化合物： 其中： R1和R2独立地选自选自取代的C1-C20烷基，取代的C3-C8环烷基，取代的芳香基和取代的杂芳基，或者R1和R2连同它们所附着的氮原子组成一个可选取代的饱和或不饱和环，该环可以选择进一步包含来自O、N和S的进一步杂原子，并且可以选择进一步融合到一个或多个其他环中； Ar选自选自取代的芳香基和取代的杂芳基； L是一个连接基，可以是直接键或选自可选取代的C2烯基和可选取代的C2炔基的群体； T独立地选自群体，包括： R3、R4和R9独立地选自氢，可选取代的C1-C10烷基，可选取代的C3-C8环烷基和可选取代的C1-C10甲氧基基团，或者选自R3、R4和R9中的一对基团，连同它们所附着的碳原子组成一个可选取代的饱和或不饱和环，该环可以选择进一步包含来自O、N和S的一个或多个杂原子，并且可以选择进一步融合到一个或多个其他环中； R5选自氢，可选取代的C1-C8烷基，可选取代的C3-C8环烷基和可选取代的芳香基团； R6选自可选取代的C1-C8烷基，可选取代的C1-C8全氟烷基，可选取代的C3-C8环烷基，可选取代的芳香基和可选取代的杂芳基； R7选自可选取代的C1-C30烷基，其中烷基的一个或多个碳原子可选择用O、S、NR8、羰基或硫代羰基中的一个或多个替换；可选取代的C3-C8环烷基；可选取代的C2-C12烯基，其中烯基的一个或多个碳原子可选择用O、S、NR8、羰基或硫代羰基中的一个或多个替换；可选取代的C2-C8炔基，其中炔基的一个或多个碳原子可选择用O、S、NR8、羰基或硫代羰基中的一个或多个替换；可选取代的C3-C12甲氧基；可选取代的芳香基；和可选取代的杂芳基；其中R8是氢或R6，n为1到10的整数。 这些化合物能够进行电荷传输，并在有机光伏器件中应用，例如染料敏化太阳能电池。
• Dithienopyrrole-benzodithiophene based donor materials for small molecular BHJSCs: Impact of side chain and annealing treatment on their photovoltaic properties
  作者：Manohar Reddy Busireddy、Venkata Niladri Raju Mantena、Narendra Reddy Chereddy、Balaiah Shanigaram、Bhanuprakash Kotamarthi、Subhayan Biswas、Ganesh Datt Sharma、Jayathirtha Rao Vaidya

  DOI：10.1016/j.orgel.2016.07.003

  日期：2016.10

  Two small molecular organic materials denoted as ICT1 and ICT2 with A-D-1-D-2-D-1-A architecture have been synthesized and their thermal, photo-physical, electrochemical and photovoltaic properties are explored. Synthesized materials have n-butylrhodanine acceptor (A), dithienopyrrole (DTP) (D-1) and benzodithiophene (BDT) (D-2) (Alkoxy BDT and alkylthiophene BDT, respectively for ICT1 and ICT2) donor moieties. Both the materials have good solubility (up to 25 mg/mL) in most common organic solvents and have excellent thermal stability with the decomposition temperature (T-d) as 348 and 382 degrees C, respectively for ICT1 and ICT2. Both ICT1 and ICT2 have broad and intense visible region absorption (molar excitation coefficient is 1.71 x 10(5) and 1.65 x 10(5) mol(-1) cm(-1), respectively for ICT1 and ICT2) and have suitable HOMO and LUMO energy levels for PC71BM acceptor. Bulk heterojunction solar cells with ITO/PEDOT: PSS/blend/Al structure are fabricated using these materials. The BHJSCs fabricated by spin cast of ICT1: PC71BM and ICT2: PC71BM (1: 2 wt ratio) blend from chloroform showed power conversion efficiency (PCE) of 2.77% (J(sc) = 6.84 mA/cm(2), V-oc = 0.92 V and FF = 0.44) and 3.27% (J(sc) = 7.26 mA/cm(2), V-oc = 0.96 V and FF = 0.47), respectively. Annealing the active layer significantly improved the PCE of these BHJSCs to 5.12% (J(sc) = 10.15 mA/cm(2), V-oc = 0.87 V and FF = 0.58) and 5.90% (J(sc) = 10.68 mA/cm(2), V-oc = 0.92 V and FF = 0.60), respectively for ICT1 and ICT2 donors. The enhancement in the PCE is due to higher light harvesting ability of the active layer, better nanoscale morphology for efficient and balanced charge transport and effective exciton dissociation at the donor-acceptor interface. (C) 2016 Elsevier B.V. All rights reserved.
• N-Alkyl- and N-aryl-dithieno[3,2-b:2′,3′-d]pyrrole-containing organic dyes for efficient dye-sensitized solar cells
  作者：Akhil Gupta、Melissa M.A. Kelson、Vanessa Armel、Ante Bilic、Sheshanath V. Bhosale

  DOI：10.1016/j.tet.2014.02.002

  日期：2014.3

  Two new organic sensitizers, 2-cyano-3-(6-(4-(diphenylamino)phenyl)-4-(2-ethylhexyl)-4H-dithieno 13,2-b:2',3'-d]pyrrol-2-yl)acrylic acid and 2-cyano-3-(6-(4-(diphenylamino)phenyl)-4-(4-(hexyloxy) phenyl)-4H-dithieno[3,2-b:2',3'-d]pyrrol-2-yl)acrylic acid, consisting of electron donating (triphenylamine) and electron accepting (cyanoacrylic acid) functionalities linked by two different rigidified pi-spacers, N-alkyl- and N-aryl-dithieno[3,2-b:2',3'-d]pyrrole, were designed, synthesized and applied for dye-sensitized solar cells, respectively. The materials were successfully synthesized through Knoevenagel condensation reactions. Ultraviolet-visible absorption spectra revealed that the use of either of rigidified pi-spacer resulted in similar charge transfer transition, however, enhanced spectral response was observed when compared with an oligothiophene analogue. In terms of their photovoltaic performance, new dyes outperformed the reference bithiophene sensitizer when tested with nitrile-based and ionic liquid-based electrolytes. (C) 2014 Elsevier Ltd. All rights reserved.
• Appalanaidu, Ejjurothu; Busireddy, Manohar Reddy; Reddy, B.V. Subba, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2020, vol. 59, # 3, p. 385 - 392
  作者：Appalanaidu, Ejjurothu、Busireddy, Manohar Reddy、Reddy, B.V. Subba、Rao, Vaidya Jayathirtha

  DOI：——

  日期：——