Conjugated copolymers bearing 2,7-di(thiophen-2-yl)phenanthrene-9,10-dione units and alteration of their emission via functionalization of the ortho-dicarbonyl groups into quinoxaline and phenazine derivatives

被引:8
作者
Alameddine, Bassam [1 ]
Baig, Noorullah [1 ]
Shetty, Suchetha [1 ]
Al-Mousawi, Saleh [2 ]
机构
[1] Gulf Univ Sci & Technol, Dept Math & Nat Sci, Kuwait, Kuwait
[2] Univ Kuwait, Dept Chem, Kuwait, Kuwait
关键词
Reactive polymers; Conjugated polymers; Gel permeation chromatography (GPC); Fluorescence; FIELD-EFFECT TRANSISTORS; HIGH-PERFORMANCE; POLYMER SEMICONDUCTOR; DIKETOPYRROLOPYRROLE; MOBILITY; POSITIONS; DONOR;
D O I
10.1016/j.polymer.2019.121589
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Conjugated copolymers were prepared from 2,7-di(thiophen-2-yl)phenanthrene-9,10-dione units with various polycyclic aromatic hydrocarbon moieties, namely, fluorene (PQF1-2), carbazole (PQC), and silafluorene (PQS). Employing mild condensation reaction conditions, PQF1-2 copolymers underwent post-modification of their ortho-dicarbonyl groups into quinoxaline- (PQF3-4) and phenazine- (PQF5-6) derivatives. The copolymers PQF1-6, PQC, and PQS were characterized by different analytical techniques, such as, gel permeation chromatography (GPC), thermogravimetric analysis (TGA), H-1- and C-13 nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR), UV-vis absorption, and emission spectroscopy. Post-modification of copolymers PQF1-2 led to interesting changes in the emission properties where the quinoxaline-containing copolymers PQF3-4 portrayed a 20-40 nm hypsochromic shift with a blue emission (similar to 470 nm) whereas copolymers PQF5-6 bearing the more aromatically extended phenazine-units revealed a similar to 55 nm bathochromic shift displaying a green emission (similar to 560 nm).
引用
收藏
页数:9
相关论文
共 49 条
  • [1] Laterally stretched polycyclic aromatic hydrocarbons: synthesis of dibenzophenanthroheptaphene and tetrabenzotriphenylenopyranthrene derivatives
    Alameddine, Bassam
    Anju, Rajamohanan Sobhana
    Shetty, Suchetha
    Baig, Noorullah
    Al-Sagheer, Fakhreia
    Al-Mousawi, Saleh
    Jenny, Titus Andreas
    [J]. NEW JOURNAL OF CHEMISTRY, 2017, 41 (13) : 6025 - 6032
  • [2] Tribenzopentaphene derivatives with lateral aromatic groups: the effect of the nature and position of substituents on emission properties
    Alameddine, Bassam
    Anju, Rajamohanan Sobhana
    Al-Sagheer, Fakhreia
    Jenny, Titus A.
    [J]. NEW JOURNAL OF CHEMISTRY, 2016, 40 (12) : 10363 - 10370
  • [3] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
    Barder, TE
    Walker, SD
    Martinelli, JR
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4685 - 4696
  • [4] Incorporation of Thieno[3,2-b]pyrrole into Diketopyrrolopyrrole-Based Copolymers for Efficient Organic Field Effect Transistors
    Bulumulla, Chandima
    Kularatne, Ruvanthi N.
    Gunawardhana, Ruwan
    Nguyen, Hien Q.
    McCandless, Gregory T.
    Biewer, Michael C.
    Stefan, Mihaela C.
    [J]. ACS MACRO LETTERS, 2018, 7 (06): : 629 - 634
  • [5] Effect of substituent groups on quinoxaline-based random copolymers on the optoelectronic and photovoltaic properties
    Cevher, Sevki Can
    Hizalan, Gonul
    Temiz, Cansel
    Udum, Yasemin Arslan
    Toppare, Levent
    Cirpan, Ali
    [J]. POLYMER, 2016, 101 : 208 - 216
  • [6] A Thieno[2,3-b]pyridine-Flanked Diketopyrrolopyrrole Polymer as an n-Type Polymer Semiconductor for All-Polymer Solar Cells and Organic Field-Effect Transistors
    Chen, Hung-Yang
    Nikolka, Mark
    Wadsworth, Andrew
    Yue, Wan
    Onwubiko, Ada
    Xiao, Mingfei
    White, Andrew J. P.
    Baran, Derya
    Sirringhaus, Henning
    McCulloch, Iain
    [J]. MACROMOLECULES, 2018, 51 (01) : 71 - 79
  • [7] Enhancing Polymer Photovoltaic Performance via Optimized Intramolecular Ester-Based Noncovalent Sulfur ••• Oxygen Interactions
    Chen, Jianhua
    Liao, Qiaogan
    Wang, Gang
    Yan, Zhenglong
    Wang, Hang
    Wang, Yulun
    Zhang, Xianhe
    Tang, Yumin
    Facchetti, Antonio
    Marks, Tobin J.
    Guo, Xugang
    [J]. MACROMOLECULES, 2018, 51 (10) : 3874 - 3885
  • [8] An Indacenodithiophene-Quinoxaline Polymer Prepared by Direct Arylation Polymerization for Organic Photovoltaics
    Chen, Shanshan
    Lee, Kyu Cheol
    Zhang, Zhi-Guo
    Kim, Dong Suk
    Li, Yongfang
    Yang, Changduk
    [J]. MACROMOLECULES, 2016, 49 (02) : 527 - 536
  • [9] Benzo[d][1,2,3]thiadiazole (isoBT): Synthesis, Structural Analysis, and Implementation in Semiconducting Polymers
    Chen, Zhihua
    Brown, Jennifer
    Drees, Martin
    Seger, Mark
    Hu, Yan
    Xia, Yu
    Boudinet, Damien
    McCray, Meko
    Delferro, Massimiliano
    Marks, Tobin J.
    Liao, Chuang-Yi
    Ko, Chung-Wen
    Chang, Yi-Ming
    Facchetti, Antonio
    [J]. CHEMISTRY OF MATERIALS, 2016, 28 (17) : 6390 - 6400
  • [10] Systematic Investigation of Side-Chain Branching Position Effect on Electron Carrier Mobility in Conjugated Polymers
    Dou, Jin-Hu
    Zheng, Yu-Qing
    Lei, Ting
    Zhang, Shi-Ding
    Wang, Zhi
    Zhang, Wen-Bin
    Wang, Jie-Yu
    Pei, Jian
    [J]. ADVANCED FUNCTIONAL MATERIALS, 2014, 24 (40) : 6270 - 6278