Copolymers of 3-arylthieno [3,2-b] thiophenes bearing different substituents: Synthesis, electronic, optical, sensor and memory properties

被引:27
作者
Gunturkun, Dilara [1 ]
Isci, Recep [1 ]
Sutay, Berkay [1 ]
Majewski, Leszek A. [2 ]
Faraji, Sheida [1 ,2 ]
Ozturk, Turan [1 ,3 ]
机构
[1] Istanbul Tech Univ, Chem Dept, TR-34469 Istanbul, Turkey
[2] Univ Manchester, Dept Elect & Elect Engn, Sackville St, Manchester M13 9PL, Lancs, England
[3] TUBITAK UME, Chem Grp Labs, TR-41470 Kocaeli 54, Turkey
关键词
Thienothiophene; Conducting polymers; Organic electronics; Sensor; Memory; FLUORIDE-ION; POLYMER; DONOR; THIENOTHIOPHENE; CHEMOSENSORS; COPLANARITY; BEHAVIOR; DEVICES;
D O I
10.1016/j.eurpolymj.2022.111167
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Thienothiophene (TT) is one of the most impressive organic cores, and has gained significant attention in the organic polymeric materials in recent years. Possessing cyano (CN), carboxylic acid (COOH) and dimethylamine (N(CH3)(2)) substituted thieno [3,4-b]thiophene (TT), pi-extended conjugated three novel polymers (P1-P3) with 3-hexylthiophene were successfully synthesized by the Suzuki coupling. All the polymers were found to be well soluble owing to the side chains. Their optical and electrochemical properties were investigated by experimental and computational studies. Moreover, the photophysical characterization of the novel polymers demonstrated a significant mega Stokes shift, reaching 138 nm with a bathochromic shift, and a changing electronic band gap between 1.91 and 2.33 eV as well as good thermal stability of degradation temperature around 320 degrees C. Also, their F- anion-recognition abilities have been investigated with selectivity of different fluoride concentration for UV and emission titration spectra. Memristive switching properties were examined by using synthesized polymers as an active layer in memory devices. The highest ON/OFF ratio of the memory devices were recorded to be 10(6) with good stability, which makes them suitable for electronic applications.
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页数:13
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共 69 条
[1]   Design and Development of a Two-Color Emissive FRET Pair Based on a Photostable Fluorescent Deoxyuridine Donor Presenting a Mega-Stokes Shift [J].
Barthes, Nicolas P. F. ;
Gavvala, Krishna ;
Bonhomme, Dominique ;
Dabert-Gay, Anne Sophie ;
Debayle, Delphine ;
Mely, Yves ;
Michel, Benoit Y. ;
Burger, Alain .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22) :10733-10741
[2]   Nonvolatile Memories Based on Graphene and Related 2D Materials [J].
Bertolazzi, Simone ;
Bondavalli, Paolo ;
Roche, Stephan ;
San, Tamer ;
Choi, Sung-Yool ;
Colombo, Luigi ;
Bonaccorso, Francesco ;
Samori, Paolo .
ADVANCED MATERIALS, 2019, 31 (10)
[3]   Anthraimidazoledione Based Reversible and Reusable Selective Chemosensors for Fluoride Ion: Naked-Eye, Colorimetric and Fluorescence "ON-OFF" [J].
Bhattacharyya, Bhaswati ;
Kundu, Arijit ;
Guchhait, Nikhil ;
Dhara, Kaliprasanna .
JOURNAL OF FLUORESCENCE, 2017, 27 (03) :1041-1049
[4]   Thieno[3,2-b]thiophene-Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices [J].
Bronstein, Hugo ;
Chen, Zhuoying ;
Ashraf, Rap Shahid ;
Zhang, Weimin ;
Du, Junping ;
Durrant, James R. ;
Tuladhar, Pabitra Shakya ;
Song, Kigook ;
Watkins, Scott E. ;
Geerts, Yves ;
Wienk, Martijn M. ;
Janssen, Rene A. J. ;
Anthopoulos, Thomas ;
Sirringhaus, Henning ;
Heeney, Martin ;
McCulloch, Iain .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3272-3275
[5]   Concise Syntheses, Polymers, and Properties of 3-Arylthieno[3,2-b]thiophenes [J].
Capan, Asli ;
Veisi, Hojat ;
Goren, Ahmet C. ;
Ozturk, Turan .
MACROMOLECULES, 2012, 45 (20) :8228-8236
[6]   Resistive switching non-volatile and volatile memory behavior of aromatic polyimides with various electron-withdrawing moieties [J].
Chen, Chih-Jung ;
Yen, Hung-Ju ;
Chen, Wen-Chang ;
Liou, Guey-Sheng .
JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (28) :14085-14093
[7]   Influence of Intramolecular Charge-Transfer Characteristics of Excitons on Polaron Generation at the Donor/Acceptor Interface in Polymer Solar Cells [J].
Chung, Hae Yeon ;
Park, Jung-Hwa ;
Cui, Junjie ;
Kim, Su-Yeon ;
Oh, Juwon ;
Kim, Dongho ;
Park, Soo Young .
JOURNAL OF PHYSICAL CHEMISTRY C, 2021, 125 (33) :18352-18361
[8]   Thienothiophenes, Dithienothiophenes, and Thienoacenes: Syntheses, Oligomers, Polymers, and Properties [J].
Cinar, Mehmet Emin ;
Ozturk, Turan .
CHEMICAL REVIEWS, 2015, 115 (09) :3036-3140
[9]   Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model [J].
Cossi, M ;
Rega, N ;
Scalmani, G ;
Barone, V .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2003, 24 (06) :669-681
[10]   First-principles study of carbon nanothreads derived from five-membered heterocyclic rings: thiophene, furan and pyrrole [J].
Demingos, Pedro G. ;
Balzaretti, Naira M. ;
Muniz, Andre R. .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2021, 23 (03) :2055-2062