Citation: Wei Song, Yang You, Tian-Jing Li, Juan Li, Liang Ding. Perylene Bisimide In-chain Polyethylene with Unique Self-assembly Nanostructure through Acyclic Diene Metathesis (ADMET) Polymerization[J]. Chinese Journal of Polymer Science, ;2018, 36(6): 703-711. doi: 10.1007/s10118-018-2067-1 shu

Perylene Bisimide In-chain Polyethylene with Unique Self-assembly Nanostructure through Acyclic Diene Metathesis (ADMET) Polymerization

Wei Song ^a,, ,
Yang You ^a ,
Tian-Jing Li ^c ,
Juan Li ^a ,
Liang Ding ^a,b,,

a.
Department of Polymer and Composite Material, School of Materials Engineering, Yancheng Institute of Technology, Yancheng 224051, China
b.
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia 19104-6323, PA, USA
c.
School of Automotive Engineering, Yancheng Vocational Institute of Industry Technology, Yancheng 224005, China

Corresponding author: Wei Song, sw121092@ycit.cn Liang Ding, dl1984911@ycit.edu.cn
Received Date: 16 September 2017
Accepted Date: 17 October 2017
Available Online: 13 February 2018

A novel perylene tetracarboxylic acid bisimide (PTCBI) in-chain polyethylene (PE) was first prepared via acyclic diene metathesis (ADMET) polymerization of PTCBI-functionalized α, ω-diene monomer. The polymers could spontaneously self-assemble into hollow cylindrical structures in which the π-π interaction between adjacent PTCBI moieties was enhanced and the electron mobility was possibly promoted. The hydrogenation of as-obtained polymer was readily accomplished, affording the desired precision PTCBI in-chain PE with a saturated backbone, which showed high glass transition temperature (T_g=63℃), relatively wide range of light absorption (λ=200-575 nm), and higher LUMO level (-3.62 eV). It can therefore serve as a superior model for facile construction of functional polyolefin and soluble PTCBI polymer with ordered architecture.
- Acyclic diene metathesis polymerization,
- Hydrogenation,
- Polyethylene,
- Perylene bisimide
1. [1]
  Zhao X. G., Ma L. C., Zhang L., Wen Y. G., Chen J. M., Shuai Z. G., Liu Y. Q., Zhan X. W.. An acetylene-containing perylene diimide copolymer for high mobility n-channel transistor in air[J]. Macromolecules, 2013,46(6):2152-2158. doi: 10.1021/ma302428x
2. [2]
  Rajaram S., Shivanna R., Kandappa S. K., Narayan K. S.. Nonplanar perylene diimides as potential alternatives to fullerenes in organic solar cells[J]. J. Phys. Chem. Lett., 2012,3(17):2405-2408. doi: 10.1021/jz301047d
3. [3]
  Lindner S. M., Hüttner S., Chiche A., Thelakkat M., Krausch G.. Charge separation at self-assembled nanostructured bulk interface in block copolymers[J]. Angew. Chem. Int. Ed., 2006,45(20):3364-3368. doi: 10.1002/(ISSN)1521-3773
4. [4]
  Rajaram S., Armstrong P. B., Kim B. J., Fréchet J. M.. Effect of addition of a diblock copolymer on blend morphology and performance of poly(3-hexylthiophene):perylene diimide solar cells[J]. Chem. Mater., 2009,21(9):1775-1777. doi: 10.1021/cm900911x
5. [5]
  Zhang Q., Cirpan A., Russell T. P., Emrick T.. Donor-acceptor poly(thiophene-block-perylene diimide) copolymers:synthesis and solar cell fabrication[J]. Macromolecules, 2009,42(4):1079-1082. doi: 10.1021/ma801504e
6. [6]
  Huang J., Wu Y., Fu H., Zhan X., Yao J., Barlow S., Marder S. R.. Photoinduced intramolecular electron transfer in conjugated perylene bisimide-dithienothiophene systems:a comparative study of a small molecule and a polymer[J]. J. Phys. Chem. A, 2009,113(17):5039-5046. doi: 10.1021/jp8107655
7. [7]
  Jiang W., Xiao C., Hao L., Wang Z., Ceymann H., Lambert C., Motta S. D., Negri F.. Localization/delocalization of charges in bay-linked perylene bisimides[J]. Chem. Eur. J., 2012,18(22):6764-6775. doi: 10.1002/chem.201103954
8. [8]
  Singh R., Giussani E., Mróz M. M., Fonzo F. D., Fazzi D., González J. C., Oldridge L., Vaenas N., Kontos A. G., Falaras P., Grimsdale A. C., Jacob J., Mullen K., Keivanidis P. E.. On the role of aggregation effects in the performance of perylene-diimide based solar cells[J]. Org. Electron., 2014,15(7):1347-1361. doi: 10.1016/j.orgel.2014.03.044
9. [9]
  Song S. F., Guo Y. T., Wang R. Y., Fu Z. S., Xu J. T., Fan Z. Q.. Synthesis and crystallization behavior of equisequential ADMET polyethylene containing arylene ether defects:remarkable effects of substitution position and arylene size[J]. Macromolecules, 2016,49(16):6001-6011. doi: 10.1021/acs.macromol.6b01324
10. [10]
  Lv A., Cui Y., Du F. S., Li Z. C.. Thermally degradable polyesters with tunable degradation temperatures via postpolymerization modification and intramolecular cyclization[J]. Macromolecules, 2016,49(22):8449-8458. doi: 10.1021/acs.macromol.6b01325
11. [11]
  Zhang H., Liu F., Cao J., Ling L., Sun R. F.. Ferrocenecontaining polymers synthesized by acyclic diene metathesis (ADMET) polymerization[J]. Chinese. J. Polym. Sci., 2016,34(2):242-252. doi: 10.1007/s10118-016-1743-2
12. [12]
  Ding L., Song W., Jiang R. Y., Zhu L.. A straightforward approach for one-pot synthesis of noncovalently connected graft copolymers with unique self-assembly nanostructures[J]. Polym. Chem., 2016,7(45):6992-7001. doi: 10.1039/C6PY01509C
13. [13]
  Li Q. B., Wang T. S., Ma C., Bai W., Bai R. K.. Facile and highly efficient strategy for synthesis of functional polyesters via tetramethyl guanidine promoted polyesterification at room temperature[J]. ACS Macro Lett., 2014,3(11):1161-1164. doi: 10.1021/mz5005184
14. [14]
  Song W., Han H. J., Wu J. H., Xie M. R.. Ladder-like polyacetylene with excellent optoelectronic properties and regular architecture[J]. Chem. Commun., 2014,50(85):12899-12902. doi: 10.1039/C4CC05524A
15. [15]
  Xie M. R., Han H. J., Jin O. Y., Du C. X.. Synthesis of ionic hybrid polymers with polyhedral oligomeric silsesquioxane pendant by acyclic diene metathesis polymerization and characterization[J]. Acta Chim. Sinica, 2013,71(10):1441-1445. doi: 10.6023/A13040377
16. [16]
  Thompson D., Yamakado R., Wagener K. B.. Extending the methylene spacer length of ADMET hydroxy-functionalized polymers[J]. Macromol. Chem. Phys., 2014,215(12):1212-1217. doi: 10.1002/macp.v215.12
17. [17]
  Rojas G., Wagener K. B.. Precisely and irregularly sequenced ethylene/1-hexene copolymers:a synthesis and thermal study[J]. Macromolecules, 2009,42(6):1934-1947. doi: 10.1021/ma802241s
18. [18]
  Li Y. F., Cao Y., Gao J., Wang D., Yu G., Heeger A. J.. Electrochemical properties of luminescent polymers and polymer light-emitting electrochemical cells[J]. Synth. Met., 1999,99(3):243-248. doi: 10.1016/S0379-6779(99)00007-7
19. [19]
  Gvishi R., Reisfeld R., Burshtein Z.. Spectroscopy and laser action of the "red perylimide dye" in various solvents[J]. Chem. Phys. Lett., 1993,213(3-4):338-344. doi: 10.1016/0009-2614(93)85142-B
20. [20]
  Xiao Z., Matsuo Y., Soga I., Nakamura E.. Structurally defined high-LUMO-level 66π-[70]fullerene derivatives:synthesis and application in organic photovoltaic cells[J]. Chem. Mater., 2012,24(13):2572-2582.
21. [21]
  Baughman T. W., Sworen J. C., Wagener K. B.. Sequenced ethylene-propylene copolymers:effects of short ethylene run lengths[J]. Macromolecules, 2006,39(15):5028-5036. doi: 10.1021/ma0602876
22. [22]
  Simocko C., Young T. C., Wagener K. B.. ADMET polymers containing precisely spaced pendant boronic acids and esters[J]. Macromolecules, 2015,48(16):5470-5473. doi: 10.1021/acs.macromol.5b01410
23. [23]
  Song W., Wu J. H., Yang G. D., Han H. J., Xie M. R., Liao X. J.. Precise perylene bisimide-substituted polyethylene with high glass transition temperature and ordered architecture[J]. RSC Adv., 2015,5(84):68765-68772. doi: 10.1039/C5RA10049F
24. [24]
  Nielsen C. B., Veldman D., Rapun R. M., Janssen R. A. J.. Copolymers of polyethylene and perylenediimides through ring-opening metathesis polymerization[J]. Macromolecules, 2008,41(4):1094-1103. doi: 10.1021/ma702350r
1. [1]
  Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
2. [2]
  Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
3. [3]
  Mengjun Zhao , Yuhao Guo , Na Li , Tingjiang Yan . Deciphering the structural evolution and real active ingredients of iron oxides in photocatalytic CO2 hydrogenation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100348-100348. doi: 10.1016/j.cjsc.2024.100348
4. [4]
  Qiang Cao , Xue-Feng Cheng , Jia Wang , Chang Zhou , Liu-Jun Yang , Guan Wang , Dong-Yun Chen , Jing-Hui He , Jian-Mei Lu . Graphene from microwave-initiated upcycling of waste polyethylene for electrocatalytic reduction of chloramphenicol. Chinese Chemical Letters, 2024, 35(4): 108759-. doi: 10.1016/j.cclet.2023.108759
5. [5]
  Xiaxia Xing , Xiaoyu Chen , Zhenxu Li , Xinhua Zhao , Yingying Tian , Xiaoyan Lang , Dachi Yang . Polyethylene imine functionalized porous carbon framework for selective nitrogen dioxide sensing with smartphone communication. Chinese Chemical Letters, 2024, 35(9): 109230-. doi: 10.1016/j.cclet.2023.109230
6. [6]
  Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO₂ adsorption and conversion: Modification methods, reaction condition, and CO₂ hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
7. [7]
  Zhihong LUO , Yan SHI , Jinyu AN , Deyi ZHENG , Long LI , Quansheng OUYANG , Bin SHI , Jiaojing SHAO . Two-dimensional silica-modified polyethylene oxide solid polymer electrolyte to enhance the performance of lithium-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 1005-1014. doi: 10.11862/CJIC.20230444
8. [8]
  Wenzhong Zhang , Zirui Yan , Lingcheng Chen , Yi Xiao . Sn-fused perylene diimides: Synthesis, mechanism, and properties. Chinese Chemical Letters, 2024, 35(10): 109582-. doi: 10.1016/j.cclet.2024.109582
9. [9]
  Jaeyong Ahn , Zhenping Li , Zhiwei Wang , Ke Gao , Huagui Zhuo , Wanuk Choi , Gang Chang , Xiaobo Shang , Joon Hak Oh . Surface doping effect on the optoelectronic performance of 2D organic crystals based on cyano-substituted perylene diimides. Chinese Chemical Letters, 2024, 35(9): 109777-. doi: 10.1016/j.cclet.2024.109777
10. [10]
  Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
11. [11]
  Xue Zhao , Mengshan Chen , Dan Wang , Haoran Zhang , Guangzhi Hu , Yingtang Zhou . Ultrafine nano-copper derived from dopamine polymerization & synchronous adsorption achieve electrochemical purification of nitrate to ammonia in complex water environments. Chinese Chemical Letters, 2024, 35(8): 109327-. doi: 10.1016/j.cclet.2023.109327
12. [12]
  Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO₃₋_x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(529)
HTML views(0)

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