9-(2,2'-bithiophen-5-yl)-3,6-di-tert-butyl-9H-carbazole | 1366299-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-(2,2'-bithiophen-5-yl)-3,6-di-tert-butyl-9H-carbazole
• 英文别名: 3,6-di-tert-butyl-9-[5-(thiophen-2-yl)thiophen-2-yl]-9H-carbazole；3,6-Ditert-butyl-9-(5-thiophen-2-ylthiophen-2-yl)carbazole
• CAS: 1366299-46-8
• 化学式: C₂₈H₂₉NS₂
• 分子量: 443.677
• InChiKey: WCSTZCBSKVINOA-UHFFFAOYSA-N

物化性质

• 沸点：
  582.9±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  9-(2,2'-bithiophen-5-yl)-3,6-di-tert-butyl-9H-carbazole 在 盐酸 、 aluminum (III) chloride 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 正丁醇 、 苯 为溶剂， 反应 59.0h， 生成
  参考文献：
  名称：

  不对称的方胺结合了咔唑作为染料敏化太阳能电池的供体

  摘要：

  制备了三个不对称的方晶，其中富电子的噻吩或联噻吩共轭片段被用于非常规地连接方酸核和咔唑（或甲基）基团。以噻吩为供体，二氢吲哚羧酸为受体的JYL-SQ1的λmax为568 nm，比一般的无金属有机染料长得多。在JYL-SQ1（形式为JYL-SQ2）中添加咔唑单元可以将λmax红移至603 nm。但是，咔唑不是强供体（并且二氢吲哚羧酸是弱受体），所有三种染料的LUMO主要在方酸单元上离域化：染料分子的激发电子注入到TiO 2中效率不高，导致短路电流和转换效率低。相应的DSSC器件对JYL-SQ1，JYL-SQ2和THL-SQ3的转换效率分别为0.71％，2.59％和2.22％。

  DOI：

  10.1002/jccs.201200250
• 作为产物：
  描述：

  3,6-二叔丁基咔唑 在 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 硝基苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 255.0h， 生成 9-(2,2'-bithiophen-5-yl)-3,6-di-tert-butyl-9H-carbazole
  参考文献：
  名称：

  不对称的方胺结合了咔唑作为染料敏化太阳能电池的供体

  摘要：

  制备了三个不对称的方晶，其中富电子的噻吩或联噻吩共轭片段被用于非常规地连接方酸核和咔唑（或甲基）基团。以噻吩为供体，二氢吲哚羧酸为受体的JYL-SQ1的λmax为568 nm，比一般的无金属有机染料长得多。在JYL-SQ1（形式为JYL-SQ2）中添加咔唑单元可以将λmax红移至603 nm。但是，咔唑不是强供体（并且二氢吲哚羧酸是弱受体），所有三种染料的LUMO主要在方酸单元上离域化：染料分子的激发电子注入到TiO 2中效率不高，导致短路电流和转换效率低。相应的DSSC器件对JYL-SQ1，JYL-SQ2和THL-SQ3的转换效率分别为0.71％，2.59％和2.22％。

  DOI：

  10.1002/jccs.201200250

文献信息

• DYES AND PHOTOELECTRIC CONVERSION DEVICES CONTAINING THE SAME
  申请人：WU Yao-Shan

  公开号：US20130261314A1

  公开（公告）日：2013-10-03

  Disclosed is a dye, having a chemical formula: wherein each R 1 is independently selected from hydrogen, —(C x H 2x+1 ), —(C y H 2y )—S—(C x H 2x+1 ), or —(C y H 2y )—N(C x H 2x+1 ) 2 ; Ar 1 is wherein each R 2 is independently selected from —(C x H 2x+1 ), —(C x H 2x )—S—(C x H 2x+1 ), or (C x H 2x )—N(C x H 2x+1 ) 2 ; Ar 2 is wherein each R 3 is independently selected from hydrogen, —(C x H 2x+1 ), —(C y H 2y)—S—(C x H 2x+1 ), or —(C y H 2y )—N(C x H 2x+1 ) 2 ; X is sulfur, oxygen, selenium, or N—R 4 , and R 4 is —(C x H 2x+1 ); m is in integer of 1 to 4; x is an integer of 1 to 20; and y is an integer of 0 to 20. The dye can be applied to a photoelectric conversion device.

  揭示了一种染料，其化学式为：其中每个R1独立地选自氢，—(CxH2x+1)，—(CyH2y)—S—(CxH2x+1)，或—(CyH2y)—N(CxH2x+1)2；Ar1为其中每个R2独立地选自—(CxH2x+1)，—(CxH2x)—S—(CxH2x+1)，或(CxH2x)—N(CxH2x+1)2；Ar2为其中每个R3独立地选自氢，—(CxH2x+1)，—(CyH2y)—S—(CxH2x+1)，或—(CyH2y)—N(CxH2x+1)2；X为硫、氧、硒，或N—R4，且R4为—(CxH2x+1)；m为1到4的整数；x为1到20的整数；y为0到20的整数。该染料可应用于光电转换装置。
• End-Capping Groups for Small-Molecule Organic Semiconducting Materials: Synthetic Investigation and Photovoltaic Applications through Direct C-H (Hetero)arylation
  作者：Te-Jui Lu、Po-Han Lin、Kun-Mu Lee、Ching-Yuan Liu

  DOI：10.1002/ejoc.201601257

  日期：2017.1.3

  A Pd-catalyzed C–H (hetero)arylation methodology has been optimized for the efficient synthesis of various useful end-capping groups that are widely applied in small-molecule optoelectronic materials. We report herein the synthesis of a broad scope of target molecules ranging from donor-type through acceptor-type to hybrid-type end-capping groups. To demonstrate their application in dye-sensitized

  Pd催化的C-H（杂）芳基化方法已被优化用于有效合成广泛应用于小分子光电材料的各种有用的封端基团。我们在此报告了范围广泛的目标分子的合成，范围从供体型到受体型到混合型封端基团。为了证明它们在染料敏化太阳能电池中的应用，我们设计了两种新的 D-A-π-A' 型有机敏化剂（CYL-3 和 CYL-4），它们是通过连续 C -H 芳基化使用容易获得的封端基团。基于 CYL-3 和 CYL-4 的器件的 Voc 值为 0.67–0.71 V，Jsc 值为 10.07–11.63 mA cm–2，FF 值为 70.6–72.9 %，对应的总功率转换效率为 4.76– 6.02%。
• Synthesis and Electronic, Photophysical, and Electrochemical Properties of a Series of Thienylcarbazoles
  作者：Shin-ichiro Kato、Satoru Shimizu、Hiroaki Taguchi、Atsushi Kobayashi、Seiji Tobita、Yosuke Nakamura

  DOI：10.1021/jo202625p

  日期：2012.4.6

  A series of thienylcarbazoles were synthesized by Suzuki-Miyaura and Ullmann coupling reactions. In these compounds, the 2-thienyl or 2,2'-bithiophen-5-yl group is connected at the N-, 1,8-, 3,6-, 2,7-, 2,7,N-, or 1,8,N-positions of the carbazole ring. The effects of structural variations on their electronic, photophysical, and electrochemical properties were explored by UV-vis and fluorescence spectroscopies, cyclic voltammetry (CV), and DFT calculations in evaluation of their potential as material components. The thienyl substituents at the 2,7-positions in 4, 5, and 10 are responsible for a high degree of pi-conjugation and strong emission with fluorescence quantum yields up to 0.61. The CV on a series of thienylcarbazoles revealed a good electron-donating ability of 3,6-substituted carbazoles 3 and 9. The number of thiophene units was found to affect the extent of pi-conjugation, the resulting HOMO-LUMO gaps, and fluorescence efficiency. The crystal structures of 5 and 9 were also disclosed.
• Molecular engineering of cyclopentadithiophene-containing organic dyes for dye-sensitized solar cell: Experimental results vs theoretical calculation
  作者：Chun-Guey Wu、Wei-Tsung Shieh、Chin-Sheng Yang、Chun-Jui Tan、Chiao-Hsin Chang、Su-Chien Chen、Chia-Yin Wu、Hui-Hsu Gavin Tsai

  DOI：10.1016/j.dyepig.2013.08.016

  日期：2013.12

  Four donor-conjugated spacer acceptor (D-pi-A) organic dyes containing cyclopentadithiophene unit as a part of the conjugated spacer are prepared and studied to investigate the effects of the conjugated spacer and donor on the short-circuit current and conversion efficiency of the correspondingDSSCs. Theoretical calculations reveal that a shorter conjugated spacer or a stronger donor leads to more effective electron injection upon photo excitation. Therefore, D-pi-A typed dye with longer conjugated spacer may have higher absorption coefficient and longer lambda(max). Nevertheless, it may also have lower effective electron injection upon photo excitation. Calculation data also show that cyclopentadithiophene although is a good moiety for extending the conjugation length of the organic dyes, it also acts as an electron sink, decreasing the effective electron injection. The transition probability calculated with the electron density difference analyses combining with the experimental absorption and photovoltaic performance data provides a useful protocol for designing organic photosensitizers for DSSCs at the electronic and structural levels. (C) 2013 Elsevier Ltd. All rights reserved.
• US8722905B2
  申请人：——

  公开号：US8722905B2

  公开（公告）日：2014-05-13