Benzo[b]selenophene/thieno[3,2-b]indole-Based N,S,Se-Heteroacenes for Hole-Transporting Layers

被引：18
|
作者：
Demina, Nadezhda S. [1 ,2 ]
Rasputin, Nikolay A. [1 ,2 ]
Irgashev, Roman A. [1 ,2 ]
Tameev, Alexey R. [1 ,3 ]
Nekrasova, Natalia, V [4 ]
Rusinov, Gennady L. [1 ,2 ]
Nunzi, Jean-Michel [5 ]
Charushin, Valery N. [1 ,2 ]
机构：
[1] Russian Acad Sci, IA Postovsky Inst Organ Synth, Ural Div, Ekaterinburg 620990, Russia
[2] Ural Fed Univ, Ekaterinburg 620002, Russia
[3] Russian Acad Sci, AN Frumkin Inst Phys Chem & Electrochem, Ekaterinburg 620990, Russia
[4] Russian Acad Sci, AN Frumkin Inst Phys Chem & Electrochem, Moscow 119071, Russia
[5] Queens Univ, Dept Phys, Dept Chem Engn Phys & Astron, Kingston, ON K7L 3N6, Canada
来源：
ACS OMEGA | 2020年 / 5卷 / 16期
基金：
俄罗斯科学基金会;
关键词：
DISORDERED ORGANIC MATERIALS; MOLECULAR-ORBITAL METHODS; BASIS-SETS; DYES; SEMICONDUCTORS; HETEROARENES; THIOPHENE; MOBILITY; FACILE; DONOR;
D O I：
10.1021/acsomega.0c00383
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Two series of new N,S,Se-heteroacenes, namely, 6H-benzo[4',S' selenopheno[2',3':4,5]thieno[3,2-b]indoles and 12H-benzo[4 '',5 '']selenopheno[2 '',3 '':4',5']thieno[2',3'4,5]thieno[3,2-b]indoles, were successfully obtained using an effective strategy based on Fiesselmann thiophene and Fischer indole synthesis. The new molecules exhibit a large optical band gap (2.82 eV < E-g(opt) < 3.23 eV) and their highest occupied molecular orbital (HOMO) energy formed by the plane pi-core ranges between -5.2 and -5.6 eV, with the narrower optical band gap and lower HOMO level corresponding to selenated heteroacenes. In thin solid films of the heteroacenes, hole mobility measured using the conventional CELIV technique ranges between 10(-5) and 10(-4) cm(2).V-1, s(-1). All these make the proposed condensed-ring compounds a promising platform for the development of hole-transporting materials applicable in organic electronics.
引用
收藏
页码：9377 / 9383
页数：7
相关论文
共 50 条
  • [41] Thieno[3,2-b]indole / 2,2′-bithiophene-based D-π-A dyes for dye sensitized solar cells
    Steparuk, Alexander S.
    Irgashev, Roman A.
    Zhilina, Ekaterina F.
    Emets, Viktor V.
    Grinberg, Vitaly A.
    Tekshina, Ekaterina, V
    Belova, Ekaterina, V
    Tolkach, Nikita M.
    Lazarenko, Petr I.
    Rusinov, Gennady L.
    Kozyukhin, Sergey A.
    DYES AND PIGMENTS, 2024, 222
  • [42] Synthesis of aryl-substituted thieno[3,2-b]thiophene derivatives and their use for N,S-heterotetracene construction
    Demina, Nadezhda S.
    Kazin, Nikita A.
    Rasputin, Nikolay A.
    Irgashev, Roman A.
    Rusinov, Gennady L.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 2678 - 2683
  • [43] Regulating Back Electron Transfer through Donor and π-Spacer Alterations in Benzothieno[3,2-b]indole-based Dye-sensitized Solar Cells
    Nitha, P. R.
    Jayadev, V.
    Pradhan, Sourava C.
    Divya, Velayudhan V.
    Suresh, Cherumuttathu H.
    John, Jubi
    Soman, Suraj
    Ajayaghosh, Ayyappanpillai
    CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (21) : 3503 - 3512
  • [44] Judicious Molecular Design of 5H-Dithieno[3,2-b:2′,3′-d]Pyran-based Hole-Transporting Materials for Highly Efficient and Stable Perovskite Solar Cells
    Lee, Kun-Mu
    Lin, Chia-Hui
    Chang, Chia-Chi
    Yang, Ting-Yu
    Chiu, Wei-Hao
    Chu, Wei-Chen
    Chang, Ya-Ho
    Li, Sie-Rong
    Lu, Shih-, I
    Hsieh, Hsiao-Chi
    Liau, Kang-Ling
    Hu, Chia Hui
    Chen, Chih-Hung
    Liu, Yun-Shuo
    Chou, Wei-Chun
    Lee, Mandy M.
    Sun, Shih-Sheng
    Tao, Yu-Tai
    Lin, Yan-Duo
    ADVANCED SCIENCE, 2025, 12 (03)
  • [45] Thieno[3,2-b]thiophene-based linear dopant-free hole transport materials for efficient perovskite solar cells
    Zhang, Ping
    Chen, Kaixing
    Gao, Xing
    Zhang, Jin
    Zeng, Ye
    Tang, Rong
    Wu, Fei
    Zhong, Cheng
    Zhu, Linna
    DYES AND PIGMENTS, 2023, 220
  • [46] An asymmetrically substituted dithieno[3,2-b:2',3'-d]pyrrole organic small-molecule hole-transporting material for high-performance perovskite solar cells
    Jingwen Jia
    Yue Zhang
    Liangsheng Duan
    Quanping Wu
    Yu Chen
    Song Xue
    Chinese Journal of Chemical Engineering, 2022, (05) : 51 - 57
  • [47] Low-bandgap nonfullerene acceptor based on thieno[3,2-b]indole core for highly efficient binary and ternary organic solar cells
    Xie, Liang
    Zhang, Yang
    Zhuang, Wenliu
    Jeong, Sang Young
    Bian, Qingzhen
    Li, Huangfen
    Cao, Jiamin
    Liu, Wanqing
    Tan, Hua
    Woo, Han Young
    Zhang, Jian
    Wang, Ergang
    CHEMICAL ENGINEERING JOURNAL, 2022, 427
  • [48] Studien zur Chemie von thienoanellierten O,N- und S,N-haltigen Heterocyclen, 15. Mitt. [1]: Zugänge zum Thieno[3,2-b][1,4]-oxazin-, Thieno[3,2-b][1,4]thiazin-und Thienodithiazepin-GrundgerüstStudies on the Chemistry of Thienoannelated O,N- and S,N-Containing Heterocycles XV [1]: An Access to the Thieno [3,2-b][1,4]oxazine, Thieno [3,2-b][1,4]thiazine and Thienodithiazepine Ring System
    Thomas Erker
    Monatshefte für Chemie / Chemical Monthly, 1998, 129 (6-7) : 679 - 687
  • [49] Exploring the potential of end-capping acceptor engineering on indolo[3,2-b]indole-based small molecules for efficient organic and perovskite solar cells
    Zahid, Waqar Ali
    Ahmad, Muhammad Fiaz
    Akram, Waqas
    Iftikhar, Rabia
    Alsalhi, Sarah A.
    Abdelmohsen, Shaimaa A. M.
    Iqbal, Javed
    RSC ADVANCES, 2024, 14 (08) : 5248 - 5263
  • [50] Design, Synthesis, and Versatile Processing of Indolo[3,2-b]indole-Based π-Conjugated Molecules for High-Performance Organic Field-Effect Transistors
    Cho, Illhun
    Park, Sang Kyu
    Kang, Boseok
    Chung, Jong Won
    Kim, Jin Hong
    Cho, Kilwon
    Park, Soo Young
    ADVANCED FUNCTIONAL MATERIALS, 2016, 26 (17) : 2966 - 2973
12345