Citation: Guo Xiaosha, Chen Liangliang, Zhang Guanxin. Synthesis and Semiconducting Properties of 1, 4-Diketopyrrolopyrrole-based Conjugated Polymers with 2, 2, 6, 6-Tetramethyl-1-piperidinyloxyl Units in the Side Chains[J]. Chemistry, ;2020, 83(8): 711-717. shu

Synthesis and Semiconducting Properties of 1, 4-Diketopyrrolopyrrole-based Conjugated Polymers with 2, 2, 6, 6-Tetramethyl-1-piperidinyloxyl Units in the Side Chains

1.
Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190
2.
University of Chinese Academy of Sciences, Beijing, 100049

Corresponding author: Zhang Guanxin, gxzhang@iccas.ac.cn
Received Date: 9 March 2020
Accepted Date: 28 March 2020

Figures(6)

In this paper, the syntheses of two 1, 4-diketopyrrolopyrrole (DPP) based conjugated polymers, PDPP4T-1 and PDPP4T-2, in which the molar ratios of the 2, 2, 6, 6-tetramethyl-1-piperidinyloxyl (TEMPO) unit-contianing alkyl chains vs. branching alkyl chains are 1:5 and 1:10 and their semiconductor properties were reported. The test results indicated that introduction of TEMPO units in the alkyl side chains has almost no effect on their electronic configuration of polymer conjugated backbones. The thin films of PDPP4T-1 and PDPP4T-2 exhibit p-type semiconducting properties with hole mobilities up to 2.12 cm²·V^-1·s^-1, though lower than that of PDPP4T without TEMPO units in the alkyl side chains. Furthermore, their thin films were characterized with AFM and GIXRD to explore the possibilities for their performance variation.
- 2, 2, 6, 6-Tetramethyl-1-piperidinyloxy,
- 1, 4-Diketopyrrolopyrrole,
- Conjugated polymers,
- Organic field effect transistors
1. [1]
  (a) Wang H, Zhang D, Guo X, et al. Chem. Commun., 2004, (6): 670-671; (b) Yu Y, Zhang D, Tan W, et al. Bioorg. Med. Chem. Lett., 2007, 17(1): 94-96.
2. [2]
  Rajca A, Wongsriratanakul J, Rajca S. Science, 2001, 294(5546): 1503-1505.
3. [3]
  Joo Y, Agarkar V, Sung S H. Science, 2018, 359(6382): 1391-1395.
4. [4]
  (a) Matsushita M M, Kawakami H, Okabe E, et al. Polyhedron, 2005, 24(16-17): 2870-2875; (b) Noro S, Chang H, Takenobu T, et al. J. Am. Chem. Soc., 2005, 127(28): 10012-10013; (c) Wang Y, Wang H, Liu Y Q, et al. J. Am. Chem. Soc., 2006, 128(40): 13058-13059; (d) Kurata T, Koshika K, Kato F, et al. Chem. Commun., 2007, (28): 2986-2988; (e) Nakatsuji S, Aoki K, Akutsu H, et al. Bull. Chem. Soc. Jpn, 2010, 83(9): 1079-1085.
5. [5]
  (a) Rudebusch G, Zafra J, Jorner K, et al. Nat. Chem., 2016, 8: 753-759; (b) Rudebusch G, Espejo G, Zafra J, et al. J. Am. Chem. Soc., 2016, 138(38): 12648-12654; (c) Kushida T, Shirai S, Ando N. J. Am. Chem. Soc., 2017, 139(41): 14336-14339; (d) Jasiński M, Pociecha D, Monobe H, et al. J. Am. Chem. Soc., 2014136(42): 14658-14661.
6. [6]
  (a) Zhang H, Dong H, Li Y, et al. Adv. Mater., 2016, 28(34): 7466-7471. (b) Reig M, Gozálvez C, Jankauskas V, et al. Chem. Eur. J., 2016, 22(51): 18551-18558; (c) Fahrenbach A, Sampath S, Late D, et al. Nano Lett., 2012, 6(11): 9964-9971; (d) Xie Y, Shuku Y, Matsushita M, et al. Chem. Commun., 2014, (50): 4178-4180.
7. [7]
  Guo X, Facchetti A, Marks T J. Chem. Rev., 2014, 114(18): 8943-9021.
8. [8]
  Wang C, Dong H, Hu W et al. Chem. Rev., 2012, 112(4): 2208-2267.
9. [9]
  Paterson A F, Singh S, Fallon K J, et al. Adv. Mater., 2018, 30(36): 1801079.
10. [10]
  Liu Z, Zhang G, Cai Z, et al. Adv. Mater., 2014, 26(40): 6965-6977.
11. [11]
  Lei T, Wang J Y, Pei J, et al. Acc. Chem. Res., 2014, 47(4): 1117-1126.
12. [12]
  Yang Y, Liu Z, Zhang G, et al. Adv. Mater., 2019, 31(46): 1903104.
13. [13]
  Liu Z, Zhang G, Zhang D. Acc. Chem. Res., 2018, 51(6): 1422-1432.
14. [14]
  Yang Y, Liu Z, Chen L, et al. Chem. Mater., 2019, 31(5): 1800-1807.
15. [15]
  Ma J, Liu Z, Yao J, et al. Macromolecules, 2018, 51(15): 6003-6010.
16. [16]
  Yao J, Yu C, Liu Z, et al. J. Am. Chem. Soc., 2016, 138(1): 173-185.
17. [17]
  Tian J, Fu L, Liu Z, et al. Adv. Funct. Mater., 2019, 29(12): 1807176.
18. [18]
  Zheng Z, Wang J, Chen H. ChemCatChem, 2014, 6(6): 1626-1634.
1. [1]
  Mengfei He , Chao Chen , Yue Tang , Si Meng , Zunfa Wang , Liyu Wang , Jiabao Xing , Xinyu Zhang , Jiahui Huang , Jiangbo Lu , Hongmei Jing , Xiangyu Liu , Hua Xu . Epitaxial Growth of Nonlayered 2D MnTe Nanosheets with Thickness-Tunable Conduction for p-Type Field Effect Transistor and Superior Contact Electrode. Acta Physico-Chimica Sinica, 2025, 41(2): 2310029-0. doi: 10.3866/PKU.WHXB202310029
2. [2]
  You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . Efficient Photocatalytic Production of H₂O₂ over ZnO/D-A Conjugated Polymer S-scheme Heterojunction and Charge Transfer Dynamics Investigation. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-0. doi: 10.3866/PKU.WHXB202406027
3. [3]
  .
  南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积
  . CCS Chemistry, 2025, 7(0): -.
4. [4]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
5. [5]
  Bao Jia , Yunzhe Ke , Shiyue Sun , Dongxue Yu , Ying Liu , Shuaishuai Ding . Innovative Experimental Teaching for the Preparation and Modification of Conductive Organic Polymer Thin Films in Undergraduate Courses. University Chemistry, 2024, 39(10): 271-282. doi: 10.12461/PKU.DXHX202404121
6. [6]
  Ke Qiu , Fengmei Wang , Mochou Liao , Kerun Zhu , Jiawei Chen , Wei Zhang , Yongyao Xia , Xiaoli Dong , Fei Wang . A Fumed SiO₂-based Composite Hydrogel Polymer Electrolyte for Near-Neutral Zinc-Air Batteries. Acta Physico-Chimica Sinica, 2024, 40(3): 2304036-0. doi: 10.3866/PKU.WHXB202304036
7. [7]
  Minghui Wu , Markus Mühlinghaus , Xuechao Li , Chaojie Xu , Qiang Chen , Haiming Zhang , Klaus Müllen , Lifeng Chi . On-Surface Synthesis of Chevron-Shaped Conjugated Ladder Polymers Consisting of Benzo[a]azulene Units. Acta Physico-Chimica Sinica, 2024, 40(8): 2307024-0. doi: 10.3866/PKU.WHXB202307024
8. [8]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
9. [9]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
10. [10]
  Fanpeng Meng , Fei Zhao , Jingkai Lin , Jinsheng Zhao , Huayang Zhang , Shaobin Wang . Optimizing interfacial electric fields in carbon nitride nanosheet/spherical conjugated polymer S-scheme heterojunction for hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(8): 100095-0. doi: 10.1016/j.actphy.2025.100095
11. [11]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
12. [12]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
13. [13]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
14. [14]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
15. [15]
  Yuxia Luo , Xiaoyu Xie , Fangfang Chen . 药物递送魔法师——分子印迹聚合物. University Chemistry, 2025, 40(8): 202-210. doi: 10.12461/PKU.DXHX202409129
16. [16]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
17. [17]
  Zhongxin YU , Wei SONG , Yang LIU , Yuxue DING , Fanhao MENG , Shuju WANG , Lixin YOU . Fluorescence sensing on chlortetracycline of a Zn-coordination polymer based on mixed ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2415-2421. doi: 10.11862/CJIC.20240304
18. [18]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
19. [19]
  Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce₄^ⅢCe₆^Ⅳ(μ₃-O)₄(μ₄-O)₄(acac)₁₄(CH₃O)₆]·2CH₃OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
20. [20]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(706)
HTML views(240)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis and Semiconducting Properties of 1, 4-Diketopyrrolopyrrole-based Conjugated Polymers with 2, 2, 6, 6-Tetramethyl-1-piperidinyloxyl Units in the Side Chains

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

Metrics

通讯作者: 陈斌, bchen63@163.com