Broadly Applicable Synthesis of Arylated Dithieno[3,2-b:2′,3′-d]pyrroles as Building Blocks for Organic Electronic Materials

被引:6
作者
Vogt, Astrid [1 ]
Schwer, Fabian [1 ]
Foertsch, Sebastian [1 ,2 ]
Lorenz, Christoph [1 ]
Mena-Osteritz, Elena [1 ]
Aubele, Anna [1 ]
Kraus, Teresa [1 ]
Baeuerle, Peter [1 ]
机构
[1] Univ Ulm, Inst Organ Chem & Adv Mat 2, Albert Einstein Allee 11, D-89081 Ulm, Germany
[2] IFF, August Wolff Str 13, D-29699 Walsrode, Germany
关键词
cross-coupling; dithienopyrrole; heterocycles; organic solar cell; structure-property relationship; N-ARYLATION; PERFORMANCE; CARBAZOLES; POLYMER; UNITS; CUI;
D O I
10.1002/chem.202101478
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and versatile method for the N-arylation of dithieno[3,2-b:2 ',3 '-d]pyrrole (DTP) is presented. By Pd- or Cu-catalyzed coupling a variety of arenes and acenes were directly attached at the DTP-nitrogen yielding a variety of functionalized DTPs. Investigations on optical and redox properties led to valuable structure-property relationships, which were corroborated by quantum chemical calculations. Further functionalization and elongation of the conjugation of an acceptor-substituted DTP was elaborated to result in complex cruciform-type donor-acceptor oligomers, which were investigated and implemented in single material organic solar cells.
引用
收藏
页码:12362 / 12370
页数:9
相关论文
共 50 条
  • [31] Improvement of the redox stability of dithieno[3,2-b:2′,3′-d]thiophene derivatives by using bulky substituents
    Okada, Shinjiro
    Yamada, Kenji
    JOURNAL OF MOLECULAR STRUCTURE, 2013, 1037 : 256 - 263
  • [32] Synthesis and Photovoltaic Performance of Low Band Gap Dithieno[3,2-b:2′,3′-d]pyrrole-based Conjugated Copolymers
    Ren, Jing
    Chen, Wei-Ye
    Li, Feng
    Wang, Wei
    Yang, Ren-qiang
    Sun, Ming-liang
    ACTA POLYMERICA SINICA, 2018, (04): : 456 - 463
  • [33] Introducing a new 7-ring fused diindenone-dithieno[3,2-b:2',3'-d]thiophene unit as a promising component for organic semiconductor materials
    Fell, Valentin H. K.
    Cameron, Joseph
    Kanibolotsky, Alexander L.
    Hussien, Eman J.
    Skabara, Peter J.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2022, 18 : 944 - 955
  • [34] Low band gap dithieno[3,2-b:2′,3′-d]silole-containing polymers, synthesis, characterization and photovoltaic application
    Huo, Lijun
    Chen, Hsiang-Yu
    Hou, Jianhui
    Chen, Teresa L.
    Yang, Yang
    CHEMICAL COMMUNICATIONS, 2009, (37) : 5570 - 5572
  • [35] Synthesis of new dithieno[3,2-b:2′,3′-d]pyrrole (DTP) dyes for dye-sensitized solar cells: effect of substituent on photovoltaic properties
    Lu, Ziyi
    Dai, Panpan
    Wang, Chunbo
    Liang, Mao
    Zong, Xueping
    Sun, Zhe
    Xue, Song
    TETRAHEDRON, 2016, 72 (23) : 3204 - 3212
  • [36] Phenothiazine organic dyes containing dithieno[3,2-b:2′,3′-d]pyrrole (DTP) units for dye-sensitized solar cells
    Zhang, Chunyao
    Wang, Shibin
    Li, Yang
    SOLAR ENERGY, 2017, 157 : 94 - 102
  • [37] Side chain engineering on dithieno[3,2-b:2,3-d]pyrrol fused electron acceptors for efficient organic solar cells
    Feng, Haohao
    Song, Xin
    Zhang, Ming
    Yu, Jiangsheng
    Zhang, Zhuohan
    Geng, Renyong
    Yang, Linqiang
    Liu, Feng
    Baran, Derya
    Tang, Weihua
    MATERIALS CHEMISTRY FRONTIERS, 2019, 3 (04) : 702 - 708
  • [38] Organic dyes containing dithieno[2,3-d:2′,3′-d′]-thieno[3,2-b:3′,2′-b′]dipyrrole core for efficient dye-sensitized solar cells
    Wang, Zhihui
    Liang, Mao
    Tan, Yulin
    Ouyang, Liyan
    Sun, Zhe
    Xue, Song
    JOURNAL OF MATERIALS CHEMISTRY A, 2015, 3 (09) : 4865 - 4874
  • [39] Synthesis and Hole-Transporting Properties of Highly Fluorescent N-Aryl Dithieno[3,2-b:2′,3′-d]pyrrole-Based Oligomers
    Balaji, Ganapathy
    Parameswaran, Manoj
    Jin, Tan Mein
    Vijila, Chellappan
    Zhu Furong
    Valiyavettil, Suresh
    JOURNAL OF PHYSICAL CHEMISTRY C, 2010, 114 (10) : 4628 - 4635
  • [40] Dithieno[3,2-b:2′,3′-d]pyrrole-based hole transport materials for perovskite solar cells with efficiencies over 18%
    Mabrouk, Sally
    Zhang, Mengmeng
    Wang, Zhihui
    Liang, Mao
    Bahrami, Behzad
    Wu, Yungen
    Wu, Jinhua
    Qiao, Qiquan
    Yang, Shangfeng
    JOURNAL OF MATERIALS CHEMISTRY A, 2018, 6 (17) : 7950 - 7958