New narrow bandgap polymers containing 10-(4-((2-ethylhexyl)oxy)phenyl)-10H-phenothiazine/phenoxazine and 3,6-di(2-thienyl)pyrrolo[3,4-c]pyrrole-1,4-dione)-based units: synthesis and photovoltaic properties

被引:1
|
作者
Nhung Thanh Thi Truong [1 ]
Huyen Le Thi Mai [1 ]
Tam Hoang Luu [2 ]
Luan Thanh Nguyen [1 ]
Nguyen, Le-Thu T. [2 ]
Mai Ha Hoang [3 ]
Ha Phuong Ky Huynh [4 ]
Chau Duc Tran [2 ]
Ha Tran Nguyen [1 ,2 ]
机构
[1] Vietnam Natl Univ Ho Chi Minh City VNU HCM, Ho Chi Minh City Univ Technol, Natl Key Lab Polymer & Composite Mat, 268 Ly Thuong Kiet,Dist 10, Ho Chi Minh City, Vietnam
[2] Vietnam Natl Univ, Ho Chi Minh City Univ Technol HCMUT, Fac Mat Technol, 268 Ly Thuong Kiet,Dist 10, Ho Chi Minh City, Vietnam
[3] Vietnam Acad Sci & Technol, Inst Chem, 18 Viet Hoang Quoc, Hanoi, Vietnam
[4] Vietnam Natl Univ VNU HCM, Ho Chi Minh City Univ Technol, Fac Chem Engn, 268 Ly Thuong Kiet,Dist 10, Ho Chi Minh City, Vietnam
关键词
Conjugated polymers;
D O I
10.1007/s10854-021-05675-2
中图分类号
TM [电工技术]; TN [电子技术、通信技术];
学科分类号
0808 ; 0809 ;
摘要
Diketopyrrolopyrrole (DPP) is one of the most used moieties in D-A conjugated polymers for high-performance pi-extended conjugated polymer-based organic solar cells. The combination of 1,4-diketo-3,6-dithienylpyrrolo[3,4-c]pyrroles (DTDPPs) and the donor moieties 10-(4-((2-ethylhexyl)oxy)phenyl)-10H-phenothiazine (M-1), 10-(4-((2-ethylhexyl)oxy)phenyl)-10H-phenoxazine (M-2), has not been reported yet. In this report, novel low-bandgap D-A conjugated polymer derivatives including DTDPP, phenothiazine and phenoxazine were successfully synthesized via direct (hetero) arylation polymerization with in the yields of 40.94-60.77%. The obtained D-A conjugated polymers named poly(3,6-Di(2-thienyl)pyrrolo[3,4-c]pyrrole-1,4-dione)-alt-(10-(4-((2-ethylhexyl)oxy) phenyl)-10H-phenothiazine) (P-1) and poly(3,6-Di(2-thienyl)pyrrolo[3,4-c]pyrrole-1,4-dione)-alt-(10-(4-((2-ethylhexyl)oxy) phenyl)-10H-phenoxazine) (P-2) exhibited a wide range of absorption spectrum in visible light region and have a low bandgaps of 1.4-1.5 eV, as well as thermal stabilities, these D-A conjugated polymers are very promising as activated polymeric materials for organic solar cells (OSCs).
引用
收藏
页码:10194 / 10208
页数:15
相关论文
共 25 条
  • [1] New narrow bandgap polymers containing 10-(4-((2-ethylhexyl)oxy)phenyl)-10H-phenothiazine/phenoxazine and 3,6-di(2-thienyl)pyrrolo[3,4-c]pyrrole-1,4-dione)-based units: synthesis and photovoltaic properties
    Nhung Thanh Thi Truong
    Huyen Le Thi Mai
    Tam Hoang Luu
    Luan Thanh Nguyen
    Le-Thu T. Nguyen
    Mai Ha Hoang
    Ha Phuong Ky Huynh
    Chau Duc Tran
    Ha Tran Nguyen
    Journal of Materials Science: Materials in Electronics, 2021, 32 : 10194 - 10208
  • [2] Modulation of the properties of pyrrolo[3,4-c]pyrrole-1,4-dione based polymers containing 2,5-di(2-thienyl)pyrrole derivatives with different substitutions on the pyrrole unit
    Agneeswari, Rajalingam
    Shin, Insoo
    Tamilavan, Vellaiappillai
    Lee, Dal Yong
    Cho, Shinuk
    Jin, Youngeup
    Park, Sung Heum
    Hyun, Myung Ho
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (06) : 4658 - 4669
  • [3] The Synthesis and Chemical Reactivity of 3,6-Di(4-aminophenyl)pyrrolo [3,4-c] pyrrole-1,4-(2H, 5H)-dione
    Kim, Joo Young
    Kang, Yong Han
    JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2019, 63 (03): : 216 - 219
  • [4] 3,6-Di-2-pyridyl pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
    Imoda, T
    Hirota, T
    Takahashi, H
    Mizuguchi, J
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2005, 61 : O616 - O618
  • [5] Crystal structure of 3,6-bis(3-cyanophenyl)pyrrolo [3,4-c]pyrrole-1,4-dione, C20H10N4O2
    Mizuguchi, J
    Matsumoto, S
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2000, 215 (01): : 195 - 196
  • [6] Synthesis of low bandgap polymer based on 3,6-dithien-2-yl-2, 5-dialkylpyrrolo[3,4-c]pyrrole-1,4-dione for photovoltaic applications
    Zhang, Guobing
    Fu, Yingying
    Xie, Zhiyuan
    Zhang, Qing
    SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2011, 95 (04) : 1168 - 1173
  • [7] Synthesis and Characterization of Red-Emitting Poly(aryleneethynylene)s Based on 2,5-Bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP)
    Palai, Akshaya K.
    Mishra, Sarada P.
    Kumar, Amit
    Srivastava, Ritu
    Kamalasanan, Modeeparampil N.
    Patri, Manoranjan
    MACROMOLECULAR CHEMISTRY AND PHYSICS, 2010, 211 (09) : 1043 - 1053
  • [8] Crystal structure of 3,6-bis(4′-pyridyl)-pyrrolo[3,4-c]pyrrole-1,4-dione, C16H10N4O2, at 93 K
    Mizuguchi, J
    Takahashi, H
    Yamakami, H
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2002, 217 (04): : 519 - 520
  • [9] Crystal structure of 3,6-bis(4-biphenylyl)pyrrolo[3,4-c]pyrrole-1,4-dione, C30H20N2O2
    Mizuguchi, J
    Miyazaki, T
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2002, 217 (01): : 43 - 44
  • [10] Solution processable poly(2,5-dialkyl-2,5-dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione) for ambipolar organic thin film transistors
    Li, Yuning
    Sun, Bin
    Sonar, Prashant
    Singh, Samarendra P.
    ORGANIC ELECTRONICS, 2012, 13 (09) : 1606 - 1613