4H-Dithieno[3,2-b：2'，3'-d]吡咯，4-（1-辛基壬基）- | 943920-67-0

• 物质功能分类: 医药中间体 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡咯类
• 中文名称: 4H-Dithieno[3,2-b：2'，3'-d]吡咯，4-（1-辛基壬基）-
• 英文名称: 4-(heptadecan-9-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole
• 英文别名: 7-heptadecan-9-yl-3,11-dithia-7-azatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 943920-67-0
• 化学式: C₂₅H₃₉NS₂
• 分子量: 417.723
• InChiKey: YUBYNLQVIVPEFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4H-Dithieno[3,2-b：2'，3'-d]吡咯，4-（1-辛基壬基）- 在 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 甲苯 为溶剂， 反应 36.5h， 生成 5,5'-(4-(heptadecan-9-yl)-4H-dithieno[3,2-b:2',3'-d]pyrrole-2,6-diyl) dithiophene-2-carbaldehyde
  参考文献：
  名称：

  Synthesis and applications of novel acceptor–donor–acceptor organic dyes with dithienopyrrole- and fluorene-cores for dye-sensitized solar cells

  摘要：

  Four novel symmetrical organic dyes (S1-S4) configured with acceptor-donor-acceptor (A-D-A) structures containing electron donating fluorene (S1 and S2) and N-alkyl dithieno[3,2-b:2',3'-d]pyrrole (DTP) (S3 and S4) cores terminated with two anchoring cyanoacrylic acids (as electron acceptors) were synthesized and applied to dye-sensitized solar cells (DSSCs). The DSSC device based on S2 dye showed the best photovoltaic performance among S1-S4 dyes: a maximum monochromatic incident photon-to-current conversion efficiency (IPCE) of 76%, a short circuit current (J(SC)) of 12.27 mA/cm(2), an open circuit voltage (V-OC) of 0.61 V. a fill factor (FF) of 0.63, and an overall power conversion efficiency (eta) of 4.73%. Besides, the utilization of chenodoxycholic acid (CDCA) as a co-adsorbent in the DSSC device based on S3 dye showed a significant improvement in its eta value (from 3.70% to 4.31%), which is attributed to the suppression of dye aggregation on TiO2 surface and thus to increase the J(SC) value eventually. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.044
• 作为产物：
  描述：

  正辛基镁溴盐 在 tris-(dibenzylideneacetone)dipalladium(0) 、 偶氮二甲酸二异丙酯 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 一水合肼 、 三苯基膦 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 24.25h， 生成 4H-Dithieno[3,2-b：2'，3'-d]吡咯，4-（1-辛基壬基）-
  参考文献：
  名称：

  Synthesis and applications of novel acceptor–donor–acceptor organic dyes with dithienopyrrole- and fluorene-cores for dye-sensitized solar cells

  摘要：

  Four novel symmetrical organic dyes (S1-S4) configured with acceptor-donor-acceptor (A-D-A) structures containing electron donating fluorene (S1 and S2) and N-alkyl dithieno[3,2-b:2',3'-d]pyrrole (DTP) (S3 and S4) cores terminated with two anchoring cyanoacrylic acids (as electron acceptors) were synthesized and applied to dye-sensitized solar cells (DSSCs). The DSSC device based on S2 dye showed the best photovoltaic performance among S1-S4 dyes: a maximum monochromatic incident photon-to-current conversion efficiency (IPCE) of 76%, a short circuit current (J(SC)) of 12.27 mA/cm(2), an open circuit voltage (V-OC) of 0.61 V. a fill factor (FF) of 0.63, and an overall power conversion efficiency (eta) of 4.73%. Besides, the utilization of chenodoxycholic acid (CDCA) as a co-adsorbent in the DSSC device based on S3 dye showed a significant improvement in its eta value (from 3.70% to 4.31%), which is attributed to the suppression of dye aggregation on TiO2 surface and thus to increase the J(SC) value eventually. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.044

文献信息

• Novel NIR-absorbing conjugated polymers for efficient polymer solar cells: effect of alkyl chain length on device performance
  作者：Wei Yue、Yun Zhao、Shuyan Shao、Hongkun Tian、Zhiyuan Xie、Yanhou Geng、Fosong Wang

  DOI：10.1039/b818885h

  日期：——

  Three low bandgap conjugated polymers, i.e., PDTPBT-C8, PDTPBT-C6 and PDTPBT-C5, which consist of alternating N-alkyl dithieno[3,2-b:2′,3′-d]pyrrole and 2,1,3-benzothiadiazole units and carry 1-octylnonyl, 1-hexylheptyl and 1-pentylhexyl as side chains, respectively, were synthesized. These polymers show strong absorption in the wavelength range of 600–900 nm with enhanced absorption coefficient as the length of alkyl chain decreases. The film morphology of the polymers and 1-(3-methoxycarbonyl)propyl-1-phenyl-[6,6]-C-61 (PCBM) blends is also dependent on the alkyl chain length. As the length decreases, the film becomes more uniform and the domian size decreases from 400–900 nm for PDTPBT-C8 to ∼50 nm for PDTPBT-C5. Bulk heterojunction photovoltaic solar cells (PSCs) were fabricated based on the blend of the polymers and PCBM with a weight ratio of 1:3. The device performance is dramatically improved as the length of the side chain decreases, due to enhanced film absorption coefficient and improved film morphology. With the polymer PDTPBT-C5, which carries the shortest alkyl chain, power conversion efficiency (PCE) up to 2.80% has been achieved. This result indicates that optimizing the structure of the solublizing alkyl chain is also crucial for the design and synthesis of high performance PSC polymeric materials.

  合成了三种窄带隙共轭聚合物，即PDTPBT-C8，PDTPBT-C6和PDTPBT-C5，它们由交替的N-烷基二噻吩并[3,2-b:2',3'-d]吡咯和2,1,3-苯并噻二唑单元组成，并分别带有1-辛基壬基，1-己基庚基和1-戊基己基侧链。这些聚合物在600-900 nm波长范围内显示出强烈的吸收，并且随着烷基链长度的减少，吸收系数增强。聚合物和1-(3-甲氧羰基)丙基-1-苯基-[6,6]-C-61（PCBM）混合物的膜形态也取决于烷基链的长度。随着链长的减少，膜变得更加均匀，域尺寸从PDTPBT-C8的400-900 nm减小到PDTPBT-C5的约50 nm。基于聚合物和PCBM的混合物（重量比为1:3）制备了体异质结光伏太阳能电池（PSCs）。由于膜吸收系数的增强和膜形态的改善，随着侧链长度的减少，器件性能显著提高。带有最短烷基链的聚合物PDTPBT-C5，其功率转换效率（PCE）达到了2.80%。这一结果表明，优化溶解性烷基链的结构对于高性能PSCs聚合物材料的设计和合成也至关重要。
• 一种有机小分子光学诊疗探针及其制备方法与应用
  申请人：南京邮电大学

  公开号：CN112876496B

  公开（公告）日：2022-01-28

  本发明公开了一种有机小分子光学诊疗探针，并公开了该探针及其纳米颗粒水溶液的制备方法和应用。本发明的有机小分子荧光探针主要成分DTPT，以具有肿瘤靶向能力的两亲性聚合物为包覆材料，通过纳米共沉淀方法制备得到具有良好水溶性、生物相容性及靶向性的纳米颗粒，该纳米颗粒具有优良的近红外二区荧光成像、光声成像、光动力及光热转换性能，可用于近红外二区荧光成像/光声成像指导下的肿瘤靶向光热/光动力联合治疗试剂的制备。本发明设计的探针成像优异、疗效显著，作为近红外二区荧光成像/光声成像及肿瘤靶向联合治疗试剂，具有广阔的应用前景。
• NOVEL PHOTOACTIVE POLYMERS
  申请人：Leclerc Mario

  公开号：US20130048075A1

  公开（公告）日：2013-02-28

  Photoactive polymers comprising first and second co-monomer repeat units, the first co-monomer repeat unit comprising a moiety selected from the group consisting of an alkylthieno[3,4-c]pyrrole-4,6-dione moiety and a 1,3-dithiophene-5-alkylthieno[3,4-c]pyrrole-4,6-dione moiety, and the second co-monomer repeat unit comprising a moiety selected from the group consisting of a 4,4′-dialkyl-dithieno[3,2-b:2′3′-d]silole moiety, an ethylene moiety, a thiophene moiety, an N-alkylcarbazole moiety, an N-(1-alkyl)dithieno[3,2-b:2′3′-d]pyrrole moiety and a 4,8-dialkyloxylbenzo[1,2-b:3,4-b]dithiophene moiety are described herein. These polymers are suitable for use in photovoltaic cells and field effect transistors.

  本文描述了包含第一和第二共聚单体重复单元的光致聚合物，其中第一共聚单体重复单元包括从羧基[3,4-c]吡咯-4,6-二酮基团和1,3-二硫杂吡咯-5-烷基[3,4-c]吡咯-4,6-二酮基团中选择的基团，而第二共聚单体重复单元包括从4,4'-二烷基-二硫杂吡咯[3,2-b:2'3'-d]硅烷基团、乙烯基团、噻吩基团、N-烷基咔唑基团、N-(1-烷基)二硫杂吡咯[3,2-b:2'3'-d]吡咯基团和4,8-二烷氧基苯并[1,2-b:3,4-b]二噻吩基团中选择的基团。这些聚合物适用于光伏电池和场效应晶体管。
• Photoactive polymers
  申请人：Leclerc Mario

  公开号：US08816035B2

  公开（公告）日：2014-08-26

  Photoactive polymers comprising first and second co-monomer repeat units, the first co-monomer repeat unit comprising a moiety selected from the group consisting of an alkylthieno[3,4-c]pyrrole-4,6-dione moiety and a 1,3-dithiophene-5-alkylthieno[3,4-c]pyrrole-4,6-dione moiety, and the second co-monomer repeat unit comprising a moiety selected from the group consisting of a 4,4′-dialkyl-dithieno[3,2-b:2′3′-d]silole moiety, an ethylene moiety, a thiophene moiety, an N-alkylcarbazole moiety, an N-(1-alkyl)dithieno[3,2-b:2′3′-d]pyrrole moiety and a 4,8-dialkyloxylbenzo[1,2-b:3,4-b]dithiophene moiety are described herein. These polymers are suitable for use in photovoltaic cells and field effect transistors.

  本文描述了包含第一和第二共聚单体重复单元的光致聚合物，其中第一共聚单体重复单元包括从以下组中选择的基团，即烷基硫代吡咯[3,4-c]吡咯-4,6-二酮基团和1,3-二噻吩-5-烷基硫代吡咯[3,4-c]吡咯-4,6-二酮基团，第二共聚单体重复单元包括从以下组中选择的基团，即4,4'-二烷基-二噻吩[3,2-b:2'3'-d]硅烷基团、乙烯基团、噻吩基团、N-烷基咔唑基团、N-(1-烷基)二噻吩[3,2-b:2'3'-d]吡咯基团和4,8-二烷氧基苯并[1,2-b:3,4-b]二噻吩基团。这些聚合物适用于光伏电池和场效应晶体管。
• US8816035B2
  申请人：——

  公开号：US8816035B2

  公开（公告）日：2014-08-26