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
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