Citation: Meng-Yang Wang, Qiu-Jing Zhang, Qiao-Qiao Shen, Qing-Yin Li, Shi-Jie Ren. Truxene-based Conjugated Microporous Polymers via Different Synthetic Methods[J]. Chinese Journal of Polymer Science, ;2020, 38(2): 151-157. doi: 10.1007/s10118-019-2321-1 shu

Truxene-based Conjugated Microporous Polymers via Different Synthetic Methods

College of Polymer Science and Engineering, State Key Laboratory of Polymer Materials Engineering, Sichuan University, Chengdu 610065, China

Corresponding author: Qing-Yin Li, qingyinli@scu.edu.cn Shi-Jie Ren, rensj@scu.edu.cn
Received Date: 9 May 2019
Revised Date: 18 June 2019
Available Online: 29 September 2019

Four truxene-based conjugated microporous polymers (Tr-CMPs) were prepared via different synthetic methods and their structure-property relationships were studied. The polymer networks have high Brunauer-Emmett-Teller (BET) specific surface areas ranging from 554 m²·g^–1 to 1024 m²·g^–1. Pore sizes of the CMPs with different linkers are mainly located between 0.60 and 1.96 nm. Among all the Tr-CMPs, Tr-CMP4 has the highest BET surface area of 1024 m²·g^–1 and exhibits the highest H₂ uptake of 0.88 wt%. Tr-CMP2 prepared by Suzuki-Miyaura coupling reaction has the highest photoluminescence quantum yields (PLQYs) of 13.06% and CO₂ uptake of 6.25 wt%.
- Conjugated microporous polymers,
- Truxene,
- Photophysical properties,
- Gas sorption
1. [1]
  McKeown, N. B.; Gahnem, B.; Msayib, K. J.; Budd, P. M.; Tattershall, C. E.; Mahmood, K.; Tan, S.; Book, D.; Langmi, H. W.; Walton, A. Towards polymer-based hydrogen storage materials: engineering ultramicroporous cavities within polymers of intrinsic microporosity. Angew. Chem. Int. Ed. 2006, 45, 1804−1807. doi: 10.1002/(ISSN)1521-3773
2. [2]
  El-Kaderi, H. M.; Hunt, J. R.; Mendoza-Cortés, J. L.; Côté, A. P.; Taylor, R. E.; O'Keeffe, M.; Yaghi, O. M. Designed synthesis of 3D covalent organic frameworks. Science 2007, 316, 268−272. doi: 10.1126/science.1139915
3. [3]
  Wang, T. Q.; Xu, Y.; He, Z. D.; Zhou, M. H.; Huang, K. Microporous organic nanotube networks from hyper cross-linking core-shell bottlebrush copolymers for selective adsorption study. Chinese J. Polym. Sci. 2018, 36, 98−105. doi: 10.1007/s10118-018-2007-0
4. [4]
  Ben, T.; Ren, H.; Ma, S.; Cao, D.; Lan, J.; Jing, X.; Wang, W.; Xu, J.; Deng, F.; Simmons, J. M.; Qiu, S.; Zhu, G. Targeted synthesis of a porous aromatic framework with high stability and exceptionally high surface area. Angew. Chem. Int. Ed. 2009, 48, 9457−9460. doi: 10.1002/anie.200904637
5. [5]
  Jiang, J. X.; Su, F.; Trewin, A.; Wood, C. D.; Campbell, N. L.; Niu, H.; Dickinson, C.; Ganin, A. Y.; Rosseinsky, M. J.; Khimyak, Y. Z.; Cooper, A. I. Conjugated microporous poly(aryleneethynylene) networks. Angew. Chem. Int. Ed. 2007, 46, 8574−8578. doi: 10.1002/anie.v46:45
6. [6]
  Chen, L.; Yang, Y.; Jiang, D. CMPs as scaffolds for constructing porous catalytic frameworks: a built-in heterogeneous catalyst with high activity and selectivity based on nanoporous metalloporphyrin polymers. J. Am. Chem. Soc. 2010, 132, 9138. doi: 10.1021/ja1028556
7. [7]
  Jiang, J. X.; Li, Y.; Wu, X.; Xiao, J.; Adams, D. J.; Cooper, A. I. Conjugated microporous polymers with rose bengal dye for highly efficient heterogeneous organo-photocatalysis. Macromolecules 2013, 46, 8779−8783. doi: 10.1021/ma402104h
8. [8]
  Kou, Y.; Xu, Y.; Guo, Z.; Jiang, D. Supercapacitive energy storage and electric power supply using an aza-fused π-conjugated microporous framework. Angew. Chem. Int. Ed. 2011, 50, 8753−8757. doi: 10.1002/anie.201103493
9. [9]
  Liu, X.; Xu, Y.; Jiang, D. Conjugated microporous polymers as molecular sensing devices: microporous architecture enables rapid response and enhances sensitivity in fluorescence-on and fluorescence-off sensing. J. Am. Chem. Soc. 2012, 134, 8738−8741. doi: 10.1021/ja303448r
10. [10]
  Guo, L.; Cao, D. Color tunable porous organic polymer luminescent probes for selective sensing of metal ions and nitroaromatic explosives. J. Mater. Chem. C 2015, 3, 8490−8494. doi: 10.1039/C5TC01649E
11. [11]
  Chen, L.; Honsho, Y.; Seki, S.; Jiang, D. Light-harvesting conjugated microporous polymers: rapid and highly efficient flow of light energy with a porous polyphenylene framework as antenna. J. Am. Chem. Soc. 2010, 132, 6742−6748. doi: 10.1021/ja100327h
12. [12]
  Jiang, J. X.; Su, F.; Niu, H.; Wood, C. D.; Campbell, N. L.; Khimyak, Y. Z.; Cooper, A. I. Conjugated microporous poly(phenylene butadiynylene)s. Chem. Commun. 2008, 8, 486−488.
13. [13]
  Ren, S.; Dawson, R.; Laybourn, A.; Jiang, J.; Khimyak, Y.; Adams, D. J.; Cooper, A. I. Functional conjugated microporous polymers: from 1,3,5-benzene to 1,3,5-triazine. Polym. Chem. 2012, 3, 928. doi: 10.1039/c2py00585a
14. [14]
  Xu, Y.; Jin, S.; Xu, H.; Nagai, A.; Jiang, D. Conjugated microporous polymers: design, synthesis and applicatio. Chem. Soc. Rev. 2013, 42, 8012−8031. doi: 10.1039/c3cs60160a
15. [15]
  Wang, J. L.; Yan, J.; Tang, Z. M.; Xiao, Q.; Ma, Y.; Pei, J. Gradient shape-persistent π-conjugated dendrimers for light-harvesting: Synthesis, photophysical properties, and energy funneling. J. Am. Chem. Soc. 2008, 130, 9952−9962. doi: 10.1021/ja803109r
16. [16]
  Wang, J. Y.; Han, J. M.; Yan, J.; Ma, Y.; Pei, J. A mechanically interlocked [3]rotaxane as a light-harvesting antenna: synthesis, characterization, and intramolecular energy transfer. Chemistry 2009, 15, 3585−3594. doi: 10.1002/chem.v15:14
17. [17]
  Wang, J. L.; Chan, Y. T.; Moorefield, C. N.; Pei, J.; Modarelli, D. A.; Romano, N. C.; Newkome, G. R. Shape-persistent, truxene-based, nano-sized bisterpyridine ruthenium(II) complexes: synthesis and photophysical properties. Macromol. Rapid Commun. 2010, 31, 850−855. doi: 10.1002/marc.v31:9/10
18. [18]
  Jiang, Y.; Wang, J. Y.; Ma, Y.; Cui, Y. X.; Zhou, Q. F.; Pei, J. Large rigid blue-emitting π-conjugated stilbenoid-based dendrimers: synthesis and properties. Org. Lett. 2006, 8, 4287−4290. doi: 10.1021/ol0616283
19. [19]
  Luo, J.; Zhou, Y.; Niu, Z. Q.; Zhou, Q. F.; Ma, Y. G.; Pei, J. Three-dimensional architectures for highly stable pure blue emission. J. Am. Chem. Soc. 2007, 129, 11314−11315. doi: 10.1021/ja073466r
20. [20]
  Wang, L.; Jiang, Y.; Luo, J.; Zhou, Y.; Zhou, J.; Wang, J.; Pei, J.; Cao, Y. Highly efficient and color-stable deep-blue organic light-emitting diodes based on a solution-processible dendrimer. Adv. Mater. 2009, 21, 4854−4858. doi: 10.1002/adma.200901039
21. [21]
  Sun, Y. M.; Xiao, K.; Liu, Y. Q.; Wang, J. L.; Pei, J.; Yu, G.; Zhu, D. B. Oligothiophene-functionalized truxene: star-shaped compounds for organic field-effect transistors. Adv. Funct. Mater. 2005, 15, 818−822. doi: 10.1002/(ISSN)1616-3028
22. [22]
  Wang, J. L.; He, Z.; Wu, H.; Cao, Y.; Pei, J. π-Conjugated molecular heterojunctions with multi[60]fullerene: photophysical, electrochemical, and photovoltaic properties. New J. Chem. 2012, 36, 1583−1588. doi: 10.1039/c2nj40121e
23. [23]
  Lin, S. H.; Hsu, Y. C.; Lin, J. T.; Lin, C. K.; Yang, J. S. Isotruxene-derived cone-shaped organic dyes for dye-sensitized solar cells. J. Org. Chem. 2010, 75, 7877−7886. doi: 10.1021/jo101831p
24. [24]
  Zong, X.; Liang, M.; Fan, C.; Tang, K.; Li, G.; Sun, Z.; Xue, S. Design of truxene-based organic dyes for high-efficiency dye-sensitized solar cells employing cobalt redox shuttle. J. Phys. Chem. C 2012, 116, 11241−11250.
25. [25]
  Zong, X.; Liang, M.; Chen, T.; Jia, J.; Wang, L.; Sun, Z.; Xue, S. Efficient iodine-free dye-sensitized solar cells employing truxene-based organic dyes. Chem. Commun. 2012, 48, 6645−6647. doi: 10.1039/c2cc32926c
26. [26]
  Yuan, M. S.; Liu, Z. Q.; Fang, Q. Donor-and-acceptor substituted truxenes as multifunctional fluorescent probes. J. Org. Chem. 2007, 72, 7915−7922. doi: 10.1021/jo071064w
27. [27]
  Zhou, H.; Zhao, X.; Huang, T.; Lu, R.; Zhang, H.; Qi, X.; Xue, P.; Liu, X.; Zhang, X. Synthesis of star-shaped monodisperse oligo(9,9-di-n-octylfluorene-2,7-vinylene)s functionalized truxenes with two-photon absorption properties. Org. Biomol. Chem. 2011, 9, 1600−1607. doi: 10.1039/c0ob00803f
28. [28]
  Xie, Y.; Zhang, X.; Xiao, Y.; Zhang, Y.; Zhou, F.; Qi, J.; Qu, J. Fusing three perylenebisimide branches and a truxene core into a star-shaped chromophore with strong two-photon excited fluorescence and high photostability. Chem. Commun. 2012, 48, 4338−4340. doi: 10.1039/c2cc31261a
29. [29]
  Du, B.; Fortin, D.; Harvey, P. D. Singlet and triplet energy transfers in tetra-(meso-truxene)zinc(II)- and tetra-(meso-tritruxene)zinc(II) porphyrin and porphyrin-free base dendrimers. Inorg. Chem. 2011, 50, 11493−11505. doi: 10.1021/ic2013667
30. [30]
  Diring, S.; Ventura, B.; Barbieri, A.; Ziessel, R. Photoinduced energy transfer processes in hybrid organic-inorganic multichromophoric arrays arranged on a truxene-based platform. Dalton Trans. 2012, 41, 13090−13096. doi: 10.1039/c2dt30385j
31. [31]
  Sprick, R. S.; Thomas, A.; Scherf, U. Acid catalyzed synthesis of carbonyl-functionalized microporous ladder polymers with high surface area. Polym. Chem. 2010, 1, 283−285. doi: 10.1039/b9py00375d
32. [32]
  Singh, H.; Tomer, V. K.; Jena, N.; Bala, I.; Sharma, N.; Nepak, D.; De Sarkar, A.; Kailasam, K.; Pal, S. K. A porous, crystalline truxene-based covalent organic framework and its application in humidity sensing. J. Mater. Chem. A 2017, 5, 21820−21827. doi: 10.1039/C7TA05043G
33. [33]
  Battula, V. R.; Singh, H.; Kumar, S.; Bala, I.; Pal, S. K.; Kailasam, K. Natural sunlight driven oxidative homocoupling of amines by a truxene-based conjugated microporous polymer. ACS Catal. 2018, 8, 6751−6759. doi: 10.1021/acscatal.8b00623
34. [34]
  Xu, Y.; Mao, N.; Feng, S.; Zhang, C.; Wang, F.; Chen, Y.; Zeng, J.; Jiang, J. X. Perylene-containing conjugated microporous polymers for photocatalytic hydrogen evolution. Macromol. Chem. Phys. 2017, 218, 1700049. doi: 10.1002/macp.v218.14
35. [35]
  Ren, S.; Dawson, R.; Adams, D. J.; Cooper, A. I. Low band-gap benzothiadiazole conjugated microporous polymers. Polym. Chem. 2013, 4, 5585−5590. doi: 10.1039/c3py00690e
36. [36]
  Sing, K. S. W.; Everett, D. H.; Haul, R. A. W.; Moscou, L.; Pierotti, R. A.; Rouquerol, J.; Siemieniewska, T. Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity (Provisional). Pure Appl. Chem. 1985, 57, 603−619. doi: 10.1351/pac198557040603
1. [1]
  Shengwen Guan , Zhaotong Wei , Ningxu Han , Yude Wei , Bin Xu , Ming Wang , Junjuan Shi . Construction of metallo-complexes with 2,2′:6′,2″-terpyridine substituted triphenylamine in different modified positions and their photophysical properties. Chinese Chemical Letters, 2024, 35(7): 109348-. doi: 10.1016/j.cclet.2023.109348
2. [2]
  Jiaxiang Guo , Zeyi Li , Tianyu Zhang , Xinyu Tian , Yue Wang , Chuandong Dou . Thienothiophene-centered ladder-type π-systems that feature distinct quinoidal π-extension. Chinese Chemical Letters, 2024, 35(5): 109337-. doi: 10.1016/j.cclet.2023.109337
3. [3]
  Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368
4. [4]
  Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
5. [5]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
6. [6]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
7. [7]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
8. [8]
  Long TANG , Yaxin BIAN , Luyuan CHEN , Xiangyang HOU , Xiao WANG , Jijiang WANG . Syntheses, structures, and properties of three coordination polymers based on 5-ethylpyridine-2,3-dicarboxylic acid and N-containing ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1975-1985. doi: 10.11862/CJIC.20240180
9. [9]
  Yikun Wang , Qiaomei Chen , Shijie Liang , Dongdong Xia , Chaowei Zhao , Christopher R. McNeill , Weiwei Li . Near-infrared double-cable conjugated polymers based on alkyl linkers with tunable length for single-component organic solar cells. Chinese Chemical Letters, 2024, 35(4): 109164-. doi: 10.1016/j.cclet.2023.109164
10. [10]
  Xiaoyan Peng , Xuanhao Wu , Fan Yang , Yefei Tian , Mingming Zhang , Hongye Yuan . Gas sensors based on metal-organic frameworks: challenges and opportunities. Chinese Journal of Structural Chemistry, 2024, 43(3): 100251-100251. doi: 10.1016/j.cjsc.2024.100251
11. [11]
  Hongxia Li , Xiyang Wang , Du Qiao , Jiahao Li , Weiping Zhu , Honglin Li . Mechanism of nanoparticle aggregation in gas-liquid microfluidic mixing. Chinese Chemical Letters, 2024, 35(4): 108747-. doi: 10.1016/j.cclet.2023.108747
12. [12]
  Chenlu Huang , Xinyu Yang , Qingyu Yu , Linhua Zhang , Dunwan Zhu . Gas-generating polymersomes-based amplified photoimmunotherapy for abscopal effect and tumor metastasis inhibition. Chinese Chemical Letters, 2024, 35(6): 109680-. doi: 10.1016/j.cclet.2024.109680
13. [13]
  Yu Deng , Yan Liu , Yonghui Deng , Jinsheng Cheng , Yidong Zou , Wei Luo . In situ sulfur-doped mesoporous tungsten oxides for gas sensing toward benzene series. Chinese Chemical Letters, 2024, 35(7): 108898-. doi: 10.1016/j.cclet.2023.108898
14. [14]
  Haoyang Wang , Ronghao Zhang , Yanlun Ren , Li Zhang . A convenient method for measuring gas-liquid volumetric mass transfer coefficient in micro reactors. Chinese Chemical Letters, 2024, 35(4): 108833-. doi: 10.1016/j.cclet.2023.108833
15. [15]
  Shuanglin TIAN , Tinghong GAO , Yutao LIU , Qian CHEN , Quan XIE , Qingquan XIAO , Yongchao LIANG . First-principles study of adsorption of Cl₂ and CO gas molecules by transition metal-doped g-GaN. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1189-1200. doi: 10.11862/CJIC.20230482
16. [16]
  Xin Zhang , Junyu Chen , Xiang Pei , Linxin Yang , Liang Wang , Luona Chen , Guangmei Yang , Xibo Pei , Qianbing Wan , Jian Wang . Drug-loading ZIF-8 for modification of microporous bone scaffold to promote vascularized bone regeneration. Chinese Chemical Letters, 2024, 35(6): 108889-. doi: 10.1016/j.cclet.2023.108889
17. [17]
  Zhenzhen Zhao , Meichen Jiao , Jiejie Ling , Han Jiang , Yan Gao , Hao Xu , Hai-Qing Li , Jingang Jiang , Peng Wu , Le Xu . Toward the microporous zeolite family with tunable large-medium cage and pore opening. Chinese Journal of Structural Chemistry, 2024, 43(9): 100336-100336. doi: 10.1016/j.cjsc.2024.100336
18. [18]
  Zixu Xie , Pengfei Zhang , Ziyao Zhang , Chen Chen , Xing Wang . The choice of antimicrobial polymers: Hydrophilic or hydrophobic?. Chinese Chemical Letters, 2024, 35(9): 109768-. doi: 10.1016/j.cclet.2024.109768
19. [19]
  Zhihao Gu , Jiabo Le , Hehe Wei , Zehui Sun , Mahmoud Elsayed Hafez , Wei Ma . Unveiling the intrinsic properties of single NiZnFeO_x entity for promoting electrocatalytic oxygen evolution. Chinese Chemical Letters, 2024, 35(4): 108849-. doi: 10.1016/j.cclet.2023.108849
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1720)
HTML views(67)

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