Citation: Zhi-Jun Wei, Ye-Wei Xu, Lin Zhang, Mei-Ming Luo. Synthesis and thermal polymerization of perylene bisimide containing benzocyclobutene groups[J]. Chinese Chemical Letters, ;2014, 25(10): 1367-1370. doi: 10.1016/j.cclet.2014.04.022 shu

Synthesis and thermal polymerization of perylene bisimide containing benzocyclobutene groups

Zhi-Jun Wei ^a,c ,
Ye-Wei Xu ^b ,
Lin Zhang ^c,, ,
Mei-Ming Luo ^a,,

1.
a Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China;
2.
b Engineering Research Center of Biomass Materials, Ministry of Education, School of Material Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, China;
3.
c Research Center of Laser Fusion, China Academy of Engineering Physics, Mianyang 621900, China

Corresponding author: Lin Zhang, Mei-Ming Luo,
Received Date: 14 January 2014
Available Online: 10 April 2014
Fund Project:

Fourfold benzocyclobutene-functionalized perylene bisimide (PBI 4) has been synthesized and its structure was characterized by FTIR, MS and NMR. PBI 4 can react either with itself, or the appropriate dienophiles to form the corresponding products under appropriate temperature. The polymer film obtained from the reaction of PBI 4 with methyl vinyl silicone rubber possessed excellent film forming properties including flatness. The optical properties of PBI 4 and polymer film obtained from the reaction of PBI 4 and methyl vinyl silicone rubber have been determined by UV/vis and fluorescence spectroscopy.
- Perylene bisimide,
- Benzocyclobutene,
- Thermopolymerization,
- Optical properties
1. [1]
  [1] A. Hermann, K. Müllen, From industrial colorants to single photon sources and biolabels: the fascination and function of rylene dyes, Chem. Lett. 35 (2006) 978-985.
2. [2]
  [2] F. Würthner, Perylene bisimide dyes as versatile building blocks for functional supramolecular architecures, Chem. Commun. 14 (2004) 1564-1579.
3. [3]
  [3] C. Backes, F. Hauke, A. Hirsch, The potential of perylene bisimide derivatives for the solubilization of carbon nanotubes and grapheme, Adv. Mater. 23 (2011) 2588-2601.
4. [4]
  [4] R.K. Dubey, A. Efimov, H. Lemmetyinen, 1,7-and 1,6-regioisomers of diphenoxy and dipyrrolidinyl substituted perylene diimides: synthesis, separation, characterization, and comparison of electrochemical and optical properties, Chem. Mater. 23 (2011) 778-788.
5. [5]
  [5] K. Mahata, P.D. Frischmann, F. Würthner, Giant electroactive M4L6 tetrahedral host self-assembled with Fe(Ⅱ) vertices and perylene bisimide dye edges, J. Am. Chem. Soc. 135 (2013) 15656-15661.
6. [6]
  [6] Z. Chen, A. Lohr, C.R. Saha-Möller, F. Würthner, Self-assembled p-stacks of functional dyes in solution: structural and thermodynamic features, Chem. Soc. Rev. 38 (2009) 564-584.
7. [7]
  [7] L. Zhang, Y. Xu, F. Zhu, J. Sun, Synthesis and characterization of thermally-stable and soluble perylene bisimide, Asian J. Chem. 22 (2010) 7135-7144.
8. [8]
  [8] Y. Shi, H. Qian, Y. Li, W. Yue, Z. Wang, Copper-mediated domino process for the synthesis of tetraiodinated di(perylene bisimide), Org. Lett. 10 (2008) 2337-2340.
9. [9]
  [9] C. Zhao, Y. Zhang, R. Li, Y. Li, J. Jiang, Di(alkoxy)-and di(alkylthio)-substituted perylene-3,4;9,10-tetracarboxy diimides with tunable electrochemical and photophysical properties, J. Org. Chem. 72 (2007) 2402-2410.
10. [10]
  [10] P. Osswald, F. Würthner, Effects of bay substituents on the racemization barriers of perylene bisimides: resolution of atropo-enantiomers, J. Am. Chem. Soc. 129 (2007) 14319-14326.
11. [11]
  [11] Y. Avlasevich, C. Li, K. Müllen, Synthesis and applications of core-enlarged perylene dyes, J. Mater. Chem. 20 (2010) 3814-3826.
12. [12]
  [12] L. Feng, Z. Chen, Synthesis and photoluminescent properties of polymer containing perylene and fluorene units, Polymers 46 (2005) 3952-3956.
13. [13]
  [13] Y. Liu, C. Yang, Y. Li, et al., Synthesis and photovoltaic characteristics of novel copolymers containing poly(phenylenevinylene) and triphenylamine moieties connected at 1,7 bay positions of perylene bisimide, Macromolecules 38 (2005) 716-721.
14. [14]
  [14] G. Boobalan, P.M. Imran, S. Nagarajan, Synthesis of highly fluorescent and water soluble perylene bisimide, Chin. Chem. Lett. 23 (2012) 149-153.
15. [15]
  [15] X. He, H. Liu, Y. Li, et al., A new copolymer containing perylene bisimide and porphyrin moieties: synthesis and characterization, Macromol. Chem. Phys. 206 (2005) 2199-2205.
16. [16]
  [16] Q. Zhang, A. Cirpan, T.P. Russell, T. Emrick, Donor-acceptor poly(thiophene-blockperylene diimide) copolymers: synthesis and solar cell fabrication, Macromolecules 42 (2009) 1079-1082.
17. [17]
  [17] R. Ponnapati, M.J. Felipe, R. Advincula, Electropolymerizable terthiophene-terminated poly(arylether)dendrimers with naphthalene and perylene cores, Macromolecules 44 (2011) 7530-7537.
18. [18]
  [18] R. Weegen, P.A. Korevaar, P. Voudouris, et al., Small sized perylene-bisimide assemblies controlled by both cooperative and anti-cooperative assembly processes, Chem. Commun. 49 (2013) 5532-5534.
19. [19]
  [19] T. Endo, T. Koizumi, T. Takata, K. chino, Synthesis of poly(4-vinylbenzocyclobutene) and its reaction with dienophiles, J. Polym. Sci. Part A: Polym. Chem. 33 (1995) 707-715.
20. [20]
  [20] Y. Kim, J. Pyun, J.M.J. Fréchet, C.J. Hawker, C.W. Frank, The dramatic effect of architecture on the self-assembly of block copolymers at interfaces, Langmuir 21 (2005) 10444-10458.
21. [21]
  [21] J.M. Warakomski, W.C. Pike, R.A. Devries, Benzocyclobutenes as styrene monomer scavengers and molecular weight “stabilizers” in atactic and syndiotactic polystyrenes, J. Appl. Polym. Sci. 78 (2000) 2008-2015.
22. [22]
  [22] L. Schmidt-Mende, A. Fechtenkötter, K. Müllen, et al., Self-organized discotic liquid crystals for high-efficiency organic photovoltaics, Science 293 (2001) 1119-1122.
23. [23]
  [23] C. You, C.R. Saha-Möller, F. Würthner, Synthesis and electropolymerization of novel oligothiophene-functionalized perylene bisimides, Chem. Commun. 18 (2004) 2030-2031.
24. [24]
  [24] C.R. Hickenboth, J.S. Moore, S.R. White, et al., Biasing reaction pathways with mechanical force, Nature 446 (2007) 423-427.
25. [25]
  [25] E. Harth, B.V. Horn, V.Y. Lee, et al., A facile approach to architecturally defined nanoparticles via intramolecular chain collapse, J. Am. Chem. Soc. 124 (2002) 8653-8660.
26. [26]
  [26] X. Zhang, S. Rehm, M.M. Safont-Sempere, F. Würthner, Vesicular perylene dye nanocapsules as supramolecular fluorescent pH sensor systems, Nat. Chem. 1 (2009) 623-629.
27. [27]
  [27] W. Qiu, S. Chen, X. Sun, Y. Liu, D. Zhu, Suzuki coupling reaction of 1,6,7,12-tetrabromoperylene bisimide, Org. Lett. 8 (2006) 867-870.
28. [28]
  [28] A. Wicklein, A. Lang, M. Muth, M. Thelakkat, Swallow-tail substituted liquid crystalline perylene bisimides: synthesis and thermotropic properties, J. Am. Chem. Soc. 131 (2009) 14442-14453.
29. [29]
  [29] H. Wang, H. Su, H. Qian, Z. Wang, A. Xia, Structure-dependent all-optical switching in graphene-nanoribbon-like molecules: fully conjugated tri(perylene bisimides), J. Phys. Chem. 114 (2010) 9130-9135.
30. [30]
  [30] M.C.R. Delgado, E.G. Kim, D.A.S. Filho, J.L. Bredas, Tuning the charge-transport parameters of perylene diimide single crystals via end and/or core functionalization: a density functional theory investigation, J. Am. Chem. Soc. 132 (2010) 3375-3387.
1. [1]
  Weinan Hu , Li Li , Xinyu Wang , Yongqiang Zhang , Maoping Song , Linlin Shi , Xinqi Hao , Siyu Lu . Carbonized polymer dots: Illuminating synthesis pathways, optical frontiers, and photoelectronic breakthroughs. Chinese Chemical Letters, 2025, 36(11): 111612-. doi: 10.1016/j.cclet.2025.111612
2. [2]
  Weiping Guo , Ying Zhu , Hong-Hua Cui , Lingyun Li , Yan Yu , Zhong-Zhen Luo , Zhigang Zou . β-Pb₃P₂S₈: A new optical crystal with exceptional birefringence effect. Chinese Chemical Letters, 2025, 36(2): 110256-. doi: 10.1016/j.cclet.2024.110256
3. [3]
  Peng-Fei Li , Chun-Li Hu , Bo Zhang , Jiang-Gao Mao , Fang Kong . From HgGa₂(SeO₃)₄ to Hg₂Ga(SeO₃)₂F: The first Hg^Ⅰ-based selenite birefringent crystal triggered by linear groups and fluoride ions. Chinese Chemical Letters, 2026, 37(2): 110588-. doi: 10.1016/j.cclet.2024.110588
4. [4]
  Xiafeng Yang , Wushan Sun , Chen Li , Wei Bai , Qingyin Wang , Gongying Wang . Synthesis of novel isosorbide-based polycarbonates by melt chain extension method. Chinese Chemical Letters, 2026, 37(4): 111674-. doi: 10.1016/j.cclet.2025.111674
5. [5]
  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
6. [6]
  Yinghao Zhang , Ke Shao , Yihang Zhu , Haokun Zhang , Yinuo Zhuo , Huihui Bao , Yeye Ai , Yongguang Li . Unanticipated optical properties of π-conjugated cyclometalated Pt(Ⅱ) complexes for advanced information storage and anti-counterfeiting materials. Chinese Chemical Letters, 2025, 36(9): 110735-. doi: 10.1016/j.cclet.2024.110735
7. [7]
  Ying Xu , Yan Pu , Qiong Zhang , Xi Kang , Manzhou Zhu . Order-by-order control over the nonlinear optical properties of atomically precise nanoclusters. Chinese Journal of Structural Chemistry, 2025, 44(10): 100735-100735. doi: 10.1016/j.cjsc.2025.100735
8. [8]
  Ya-Xuan Xue , Han Xu , Jia-Nan Chen , Hai-Quan Tian , Tao Jia , Wei-Dong Liu , Chong-Yang Li , La-Sheng Long , Lan-Sun Zheng , Xiang-Jian Kong . Chiral Ln3Co5 clusters with geometry-dependent chiroptical and magneto-optical properties. Chinese Journal of Structural Chemistry, 2026, 45(1): 100764-100764. doi: 10.1016/j.cjsc.2025.100764
9. [9]
  Le Ye , Zi-Luo Fang , Ming-Yu Guo , Wei-Xiong Zhang . Hot-pressing boosted nonlinear optical properties in a new ferroelectric plastic crystalline material. Chinese Chemical Letters, 2026, 37(4): 110826-. doi: 10.1016/j.cclet.2025.110826
10. [10]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
11. [11]
  Shenhao QIU , Qingquan XIAO , Huazhu TANG , Quan XIE . First-principles study on electronic structure, optical and magnetic properties of rare earth elements X (X=Sc, Y, La, Ce, Eu) doped with two-dimensional GaSe. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2250-2258. doi: 10.11862/CJIC.20240104
12. [12]
  Ya-Ru Qu , Kai-Li Tian , Han-Jun Huang , Jia-Jun Tu , Ai-Hao Chen , Hai-Jun Sun , Maxim V. Bermeshev , Shao-Jie Wang , Wen-Bin Li , Xiang-Kui Ren . Fluorescence enhancement of perylene diimide: Design strategy and application. Chinese Journal of Structural Chemistry, 2025, 44(12): 100756-100756. doi: 10.1016/j.cjsc.2025.100756
13. [13]
  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
14. [14]
  Jingjing Zhang , Fei Yang , Liying Zhang , Ran Li , Guo Wang , Yanqing Xu , Wei Wei . Stable radicals in bacteria composites hybridized by a doubly-strapped perylene diimide for near-infrared photothermal conversion. Chinese Chemical Letters, 2025, 36(7): 110627-. doi: 10.1016/j.cclet.2024.110627
15. [15]
  Shuhong Wu , Wanying Han , Ying Wang , Yan Zhuang , Hui Niu , Lurong Li , Junhui Wang , Yuan Liu , Huan Lin , Kaifeng Wu , Jinni Shen , Yingguang Zhang , Michael K. H. Leung , Jinlin Long . Close π-π stacking facilitated intermolecular charge separation in self-assembled perylene monoimide for photocatalytic hydrogen production. Chinese Journal of Structural Chemistry, 2025, 44(6): 100592-100592. doi: 10.1016/j.cjsc.2025.100592
16. [16]
  Chao Wei , Zi-Yi Zhao , Jing-Jing Li , Jinli Zhang , Ming Lu , Xiao-Qin Liu , Guoliang Liu , Jiandong Pang , Lin-Bing Sun . Topology guided construction of MOF by linking Zr-MOLs with perylene diimide motifs for photocatalytic oxidation. Chinese Journal of Structural Chemistry, 2025, 44(8): 100625-100625. doi: 10.1016/j.cjsc.2025.100625
17. [17]
  Yu-Qin Xia , Shui-Ming Jing , Li-Mei Chang , Zhi-Gang Gu , Jian Zhang . Luminescent covalent organic frameworks: Classification to optical applications. Chinese Journal of Structural Chemistry, 2026, 45(1): 100731-100731. doi: 10.1016/j.cjsc.2025.100731
18. [18]
  Can Wang , Zhe Sun , Donghan Ma . Review of imaging buffers used in stochastic optical reconstruction microscopy. Chinese Chemical Letters, 2025, 36(9): 110677-. doi: 10.1016/j.cclet.2024.110677
19. [19]
  Chen Liu , Tianqi Zhao , Jialing Zhou , Xiaoyun Hu , Dinghao Pan , Jinlong Li , Wei Li , Zhihui Dai . Optical lateral flow immune assay technology for body fluid sensing. Chinese Chemical Letters, 2026, 37(1): 110967-. doi: 10.1016/j.cclet.2025.110967
20. [20]
  Matvey K. Shurikov , Yuliana A. Kolesnikova , Darya E. Votkina , Pavel A. Abramov , Taisiya S. Sukhikh , Galina V. Romanenko , Sergey L. Veber , Dmitry E. Gorbunov , Nina P. Gritsan , Giuseppe Resnati , Evgeny V. Tretyakov , Vadim Yu. Kukushkin , Pavel S. Postnikov , Pavel V. Petunin . Engineering optical anisotropy in paramagnetic organic crystals: Dichroism of nitronyl nitroxide radicals. Chinese Journal of Structural Chemistry, 2025, 44(9): 100653-100653. doi: 10.1016/j.cjsc.2025.100653

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1503)
HTML views(55)

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