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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2021年 / 27卷 / 48期

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

页码：12362 / 12370

页数：9

共 50 条

[21] Polymer solar cells based on copolymers of dithieno[3,2-b:2′,3′-d]silole and thienopyrroledione
Hong, Young-Rae
Wong, Hoi-Ka
Moh, Lionel C. H.
Tan, Huei-Shuan
Chen, Zhi-Kuan
CHEMICAL COMMUNICATIONS, 2011, 47 (17) : 4920 - 4922
[22] Synthesis and Photovoltaic Characterization of Dithieno[ 3,2-b: 2', 3'-d] thiophene-Derived Narrow-Bandgap Polymers
Zhu, Enwei
Ni, Bin
Zhao, Baofeng
Hai, Jiefeng
Bian, Linyi
Wu, Hongbin
Tang, Weihua
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2014, 215 (03) : 227 - 234
[23] A review of dithieno[3,2-b:2′,3′-d]pyrrole-based electrochromic conjugated polymers
Carbas, Buket Bezgin
Yildiz, Hueseyin Bekir
EUROPEAN POLYMER JOURNAL, 2024, 204
[24] An Air-Stable Semiconducting Polymer Containing Dithieno[3,2-b:2′,3′-d]arsole
Green, Joshua P.
Han, Yang
Kilmurray, Rebecca
McLachlan, Martyn A.
Anthopoulos, Thomas D.
Heeney, Martin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (25) : 7148 - 7151
[25] Synthesis, electropolymerization and functionalization via click chemistry of N-alkynylated dithieno[3,2-b:2′,3′-d]pyrrole
Bandera, Yuriy
Jones, Haley W.
Grant, Benjamin
Mell, Sarah
Foulger, Stephen H.
RSC ADVANCES, 2022, 12 (45) : 29187 - 29196
[26] Multi-mode emission color tuning of dithieno[3,2-b:2′,3′-d]arsoles
Imoto, Hiroaki
Kawashima, Ikuo
Yamazawa, Chieko
Tanaka, Susumu
Naka, Kensuke
JOURNAL OF MATERIALS CHEMISTRY C, 2017, 5 (27) : 6697 - 6703
[27] Organic Dyes Incorporating the Dithieno[3,2-b:2′,3′-d]thiophene Moiety for Efficient Dye-Sensitized Solar Cells
Yang, Hsiu-Yi
Yen, Yung-Sheng
Hsu, Ying-Chan
Chou, Hsien-Hsin
Lin, Jiann T.
ORGANIC LETTERS, 2010, 12 (01) : 16 - 19
[28] Dithieno[3,2-b:2,3-d]arsole-containing conjugated polymers in organic photovoltaic devices
Green, Joshua P.
Cha, Hyojung
Shahid, Munazza
Creamer, Adam
Durrant, James R.
Heeney, Martin
DALTON TRANSACTIONS, 2019, 48 (20) : 6676 - 6679
[29] Vacuum processable donor material based on dithieno[3,2-b:2′,3′-d]thiophene and pyrene for efficient organic solar cells
Kwon, Jongchul
Kim, Tae-Min
Oh, Hong-Se
Kim, Jang-Joo
Hong, Jong-In
RSC ADVANCES, 2014, 4 (47): : 24453 - 24457
[30] Design and photovoltaic characterization of dithieno[3,2-b:2′,3′-d]silole copolymers with positioning phenyl groups
Zhu, Enwei
Luo, Guoping
Liu, Yun
Yu, Jiangsheng
Zhang, Fujun
Che, Guangbo
Wu, Hongbin
Tang, Weihua
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2014, 16 (48) : 26893 - 26900

← 1 2 3 4 5 →