Citation: Li Meng, Lin Wei-Bin, Fang Lei, Chen Chuan-Feng. Recent Progress on Circularly Polarized Luminescence of Chiral Organic Small Molecules[J]. Acta Chimica Sinica, ;2017, 75(12): 1150-1163. doi: 10.6023/A17090440 shu

Recent Progress on Circularly Polarized Luminescence of Chiral Organic Small Molecules

Li Meng ^a ,
Lin Wei-Bin ^a,b ,
Fang Lei ^a,b ,
Chen Chuan-Feng ^a,b,,

a.
CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Chen Chuan-Feng, cchen@iccas.ac.cn
Received Date: 28 September 2017
Available Online: 1 December 2017
Fund Project: the National Natural Science Foundation of China 21602224the Strategic Priority Research Program of Chinese Academy of Sciences XDB12010400the National Natural Science Foundation of China 21572233the National Natural Science Foundation of China 51373180Project supported by the National Natural Science Foundation of China (Nos. 21602224, 51373180, 21572233), and the Strategic Priority Research Program of Chinese Academy of Sciences (No. XDB12010400)

Figures(28)

Circularly polarized luminescence (CPL) not only can reflect the excited state structure information of chiral system, but also has wide potential applications in 3D display, communication of spin information, information storage and processing, CPL laser and biological probe. Consequently, more and more attention and interests have been attracted into this field, which turns to be one of the most hot topics in organic luminescence materials in recent years. In this review, recent progress on the chiral organic small molecules with CPL properties is summarized. First, CPL concept and earlier studies of CPL and organic small molecules with CPL properties are briefly introduced. Then, chiral organic small molecules with CPL properties are classified into four types of central chirality, axial chirality, planar chirality, and helical chirality, and their progresses in recent years are systematically described, respectively. Among the small molecular systems with different types of chirality, those ones based on the biaryl skeleton and helicene derivatives show excellent CPL properties, and they could also be controlled or switched by anions, protons and others. Moreover, it should be paid attention to the applications of aggregation induced effect (AIE) and supramolecular chemistry for the chiral organic small molecules to obtain better CPL property. Finally, a conclusion and perspective on CPL materials based on chiral small molecules is provided.
- circularly polarized luminescence,
- chirality,
- helicene,
- organic small molecule
1. [1]
  (a) Brittain, H. G. Chirality 1996, 8, 357;(b) Riehl, J. P.; Richardson, F. S. Chem. Rev. 1986, 86, 1.
2. [2]
  Muller, G. Luminescence of Lanthanide Ions in Coordination Compounds and Nanomaterials, Ed.: de Bettencourt-Dias, A., Wiley, Hoboken, 2014, pp. 77~124.
3. [3]
  Yang, Y.; da Costa, R. C.; Smilgies, D.-M.; Campbell, A. J.; Fuchter, M. J. Adv. Mater. 2013, 25, 2624. doi: 10.1002/adma.201204961
4. [4]
  Farshchi, R.; Ramsteiner, M.; Herfort, J.; Tahraoui, A.; Grahn, H. T. Appl. Phys. Lett. 2011, 98, 162508. doi: 10.1063/1.3582917
5. [5]
  Yang, Y.; da Costa, R. C.; Fuchter, M. J.; Campbell, A. J. Nat. Photon. 2013, 7, 634. doi: 10.1038/nphoton.2013.176
6. [6]
  Jiménez, J.; Cerdán, L.; Moreno, F.; Maroto, B. L.; García-Moreno, I.; Lunkley, J. L.; Muller, G.; de la Moya, S. J. Phys. Chem. C 2017, 121, 5287. doi: 10.1021/acs.jpcc.7b00654
7. [7]
  (a) Muller, G. Dalton Trans. 2009, 9692;(b) Hassey, R.; Swain, E. J.; Hammer, N. I.; Venkataraman, D.; Barnes, M. D. Science 2006, 314, 1437.
8. [8]
  Sanchez-Carnerero, E. M.; Agarrabeitia, A. R.; Moreno, F.; Maroto, B. L.; Muller, G.; Ortiz, M. J.; de la Moya, S. Chem. Eur. J. 2015, 21, 13488. doi: 10.1002/chem.v21.39
9. [9]
  Lunkley, J. L.; Shirotani, D.; Yamanari, K.; Kaizaki, S.; Muller, G. J. Am. Chem. Soc. 2008, 130, 13814. doi: 10.1021/ja805681w
10. [10]
  (a) Carr, R.; Evans, N. H.; Parker, D. Chem. Soc. Rev. 2012, 41, 7673;(b) Aspinall, H. C. Chem. Rev. 2002, 102, 1807;(c) Bunzli, J. C. G.; Piguet, C. Chem. Rev. 2002, 102, 1897;(d) Heffern, M. C.; Matosziuk, L. M.; Meade, T. J. Chem. Rev. 2014, 114, 4496.
11. [11]
  (a) Yashima, E.; Ousaka, N.; Taura, D.; Shimomura, K.; Ikai, T.; Maeda, K. Chem. Rev. 2016, 116, 13752;(b) Watanabe, K.; Akagi, K. Sci. Technol. Adv. Mater. 2014, 15, 044203.
12. [12]
  Emeis, C. A.; Oosterhoff, L. J. Chem. Phys. Lett. 1967, 1, 129. doi: 10.1016/0009-2614(67)85007-3
13. [13]
  Barnett, C. J.; Drake, A. F.; Mason, S. F. Bull. Soc. Chim. Belg. 1979, 88, 853.
14. [14]
  Kawai, T.; Kawamura, K.; Tsumatori, H.; Ishikawa, M.; Naito, M.; Fujiki, M.; Nakashima, T. ChemPhysChem 2007, 8, 1465. doi: 10.1002/(ISSN)1439-7641
15. [15]
  Kumar, J.; Nakashima, T.; Kawai, T. J. Phys. Chem. Lett. 2015, 6, 3445. doi: 10.1021/acs.jpclett.5b01452
16. [16]
  Gossauer, A.; Fehr, F.; Nydegger, F.; Stöckli-Evans, H. J. Am. Chem. Soc. 1997, 119, 1599. doi: 10.1021/ja961883q
17. [17]
  Amako, T.; Nakabayashi, K.; Mori, T.; Inoue, Y.; Fujiki, M.; Imai, Y. Chem. Commun. 2014, 50, 12836. doi: 10.1039/C4CC04228J
18. [18]
  Ito, S.; Ikeda, K.; Nakanishi, S.; Imai, Y.; Asami, M. Chem. Commun. 2017, 53, 6323. doi: 10.1039/C7CC01351E
19. [19]
  Gobo, Y.; Yamamura, M.; Nakamura, T.; Nabeshima, T. Org. Lett. 2016, 18, 2719. doi: 10.1021/acs.orglett.6b01237
20. [20]
  (a) Kumar, J.; Nakashima, T.; Tsumatori, H.; Mori, M.; Naito, M.; Kawai, T. Chem. Eur. J. 2013, 19, 14090;(b) Kumar, J.; Nakashima, T.; Kawai, T. Langmuir 2014, 30, 6030.
21. [21]
  Sheng, Y.; Ma, J.; Liu, S.; Wang, Y.; Zhu, C.; Cheng, Y. Chem. Eur. J. 2016, 22, 9519. doi: 10.1002/chem.201600891
22. [22]
  (a) Liu, M.; Zhang, L.; Wang, T. Chem. Rev. 2015, 115, 7304;(b) Zhang, L.; Wang, T.; Shen, Z.; Liu, M. Adv. Mater. 2016, 28, 1044.
23. [23]
  Ikeda, T.; Masuda, T.; Hirao, T.; Yuasa, J.; Tsumatori, H.; Kawai, T.; Haino, T. Chem. Commun. 2012, 48, 6025. doi: 10.1039/c2cc31512b
24. [24]
  Liu, J.; Su, H.; Meng, L.; Zhao, Y.; Deng, C.; Ng, J. C. Y.; Lu, P.; Faisal, M.; Lam, J. W. Y.; Huang, X.; Wu, H.; Wong, K. S.; Tang, B. Z. Chem. Sci. 2012, 3, 2737. doi: 10.1039/c2sc20382k
25. [25]
  Li, H.; Cheng, J.; Deng, H.; Zhao, E.; Shen, B.; Lam, J. W. Y.; Wong, K. S.; Wu, H.; Li, B. S.; Tang, B. Z. J. Mater. Chem. C 2015, 3, 2399.
26. [26]
  Ye, Q.; Zhu, D.; Zhang, H.; Lu, X.; Lu, Q. J. Mater. Chem. C 2015, 3, 6997. doi: 10.1039/C5TC00987A
27. [27]
  Liu, S.; Li, F.; Wang, Y.; Li, X.; Zhu, C.; Cheng, Y. J. Mater. Chem. C 2017, 5, 6030. doi: 10.1039/C7TC01371J
28. [28]
  Yang, D.; Duan, P.; Zhang, L.; Liu, M. Nat. Commun. 2017, 8, 15727. doi: 10.1038/ncomms15727
29. [29]
  Kimoto, T.; Tajima, N.; Fujiki, M.; Imai, Y. Chem. Asian J. 2012, 7, 2836. doi: 10.1002/asia.201200725
30. [30]
  (a) Kitayama, Y.; Nakabayashi, K.; Wakabayashi, T.; Tajima, N.; Fujiki, M.; Imai, Y. RSC Adv. 2015, 5, 410;(b) Kitayama, Y.; Amako, T.; Suzuki, N.; Fujiki, M.; Imai, Y. Org. Biomol. Chem. 2014, 12, 4342.
31. [31]
  Kono, Y.; Nakabayashi, K.; Kitamura, S.; Kuroda, R.; Fujiki, M.; Imai, Y. Tetrahedron 2015, 71, 3985. doi: 10.1016/j.tet.2015.04.048
32. [32]
  Sanchez-Carnerero, E. M.; Moreno, F.; Maroto, B. L.; Agarrabeitia, A. R.; Ortiz, M. J.; Vo, B. G.; Muller, G.; de la Moya, S. J. Am. Chem. Soc. 2014, 136, 3346. doi: 10.1021/ja412294s
33. [33]
  Zhang, S.; Wang, Y.; Meng, F.; Dai, C.; Cheng, Y.; Zhu, C. Chem. Commun. 2015, 51, 9014. doi: 10.1039/C5CC01994J
34. [34]
  Sheng, Y.; Shen, D.; Zhang, W.; Zhang, H.; Zhu, C.; Cheng, Y. Chem. Eur. J. 2015, 21, 13196. doi: 10.1002/chem.201502193
35. [35]
  Wang, Y.; Li, X.; Li, F.; Sun, W.-Y.; Zhu, C.; Cheng, Y. Chem. Commun. 2017, 53, 7505. doi: 10.1039/C7CC04363E
36. [36]
  Maeda, H.; Bando, Y.; Shimomura, K.; Yamada, I.; Naito, M.; Nobusawa, K.; Tsumatori, H.; Kawai, T. J. Am. Chem. Soc. 2011, 133, 9266. doi: 10.1021/ja203206g
37. [37]
  (a) Tsumatori, H.; Nakashima, T.; Kawai, T. Org. Lett. 2010, 12, 2362;(b) Kumar, J.; Tsumatori, H.; Yuasa, J.; Kawai, T.; Nakashima, T. Angew. Chem. Int. Ed. 2015, 54, 5943.
38. [38]
  Langhals, H.; Hofer, A.; Bernhard, S.; Siegel, J. S.; Mayer, P. J. Org. Chem. 2011, 76, 990. doi: 10.1021/jo102254a
39. [39]
  Kogel, J. F.; Kusaka, S.; Sakamoto, R.; Iwashima, T.; Tsuchiya, M.; Toyoda, R.; Matsuoka, R.; Tsukamoto, T.; Yuasa, J.; Kitagawa, Y.; Kawai, T.; Nishihara, H. Angew. Chem. Int. Ed. 2016, 55, 1377. doi: 10.1002/anie.201509411
40. [40]
  (a) Morisaki, Y.; Gon, M.; Sasamori, T.; Tokitoh, N.; Chujo, Y. J. Am. Chem. Soc. 2014, 136, 3350;(b) Gon, M.; Morisaki, Y.; Chujo, Y. J. Mater. Chem. C 2015, 3, 521.
41. [41]
  Morisaki, Y.; Inoshita, K.; Chujo, Y. Chem. Eur. J. 2014, 20, 8386. doi: 10.1002/chem.201402930
42. [42]
  Gon, M.; Morisaki, Y.; Chujo, Y. Chem. Commun. 2017, 53, 8304. doi: 10.1039/C7CC03615A
43. [43]
  Shen, Y.; Chen, C.-F. Chem. Rev. 2012, 112, 1463. doi: 10.1021/cr200087r
44. [44]
  Field, J. E.; Muller, G.; Riehl, J. P.; Venkataraman, D. J. Am. Chem. Soc. 2003, 125, 11808. doi: 10.1021/ja035626e
45. [45]
  Sawada, Y.; Furumi, S.; Takai, A.; Takeuchi, M.; Noguchi, K.; Tanaka, K. J. Am. Chem. Soc. 2012, 134, 4080. doi: 10.1021/ja300278e
46. [46]
  Nakamura, K.; Furumi, S.; Takeuchi, M.; Shibuya, T.; Tanaka, K. J. Am. Chem. Soc. 2014, 136, 5555. doi: 10.1021/ja500841f
47. [47]
  Oyama, H.; Nakano, K.; Harada, T.; Kuroda, R.; Naito, M.; Nobusawa, K.; Nozaki, K. Org. Lett. 2013, 15, 2104. doi: 10.1021/ol4005036
48. [48]
  Goto, K.; Yamaguchi, R.; Hiroto, S.; Ueno, H.; Kawai, T.; Shinokubo, H. Angew. Chem. Int. Ed. 2012, 51, 10333 doi: 10.1002/anie.201204863
49. [49]
  Katayama, T.; Nakatsuka, S.; Hirai, H.; Yasuda, N.; Kumar, J.; Kawai, T.; Hatakeyama, T. J. Am. Chem. Soc. 2016, 138, 5210. doi: 10.1021/jacs.6b01674
50. [50]
  Sakai, H.; Kubota, T.; Yuasa, J.; Araki, Y.; Sakanoue, T.; Takenobu, T.; Wada, T.; Kawai, T.; Hasobe, T. J. Phys. Chem. C 2016, 120, 7860. doi: 10.1021/acs.jpcc.6b01344
51. [51]
  Shen, C.; Srebro-Hooper, M.; Jean, M.; Vanthuyne, N.; Toupet, L.; Williams, J. A. G.; Torres, A. R.; Riives, A. J.; Muller, G.; Autschbach, J.; Crassous, J. Chem. Eur. J. 2017, 23, 407. doi: 10.1002/chem.v23.2
52. [52]
  Sakai, H.; Shinto, S.; Kumar, J.; Araki, Y.; Sakanoue, T.; Takenobu, T.; Wada, T.; Kawai, T.; Hasobe, T. J. Phys. Chem. C 2015, 119, 13937. doi: 10.1021/acs.jpcc.5b03386
53. [53]
  Yamamoto, Y.; Sakai, H.; Yuasa, J.; Araki, Y.; Wada, T.; Sakanoue, T.; Takenobu, T.; Kawai, T.; Hasobe, T. J. Phys. Chem. C 2016, 120, 7421. doi: 10.1021/acs.jpcc.6b01123
54. [54]
  Sakai, H.; Kubota, T.; Yuasa, J.; Araki, Y.; Sakanoue, T.; Takenobu, T.; Wada, T.; Kawai, T.; Hasobe, T. Org. Biomol. Chem. 2016, 14, 6738. doi: 10.1039/C6OB00937A
55. [55]
  Otani, T.; Tsuyuki, A.; Iwachi, T.; Someya, S.; Tateno, K.; Kawai, H.; Saito, T.; Kanyiva, K. S.; Shibata, T. Angew. Chem. Int. Ed. 2017, 56, 3906 doi: 10.1002/anie.201700507
56. [56]
  Kaseyama, T.; Furumi, S.; Zhang, X.; Tanaka, K.; Takeuchi, M. Angew. Chem. Int. Ed. 2011, 50, 3684. doi: 10.1002/anie.v50.16
57. [57]
  (a) Shen, C.; Anger, E.; Srebro, M.; Vanthuyne, N.; Deol, K. K.; Jefferson, T. D., Jr.; Muller, G.; Williams, J. A. G.; Toupet, L.; Roussel, C.; Autschbach, J.; Reau, R.; Crassous, J. Chem. Sci. 2014, 5, 1915;(b) Saleh, N.; Srebro, M.; Reynaldo, T.; Vanthuyne, N.; Toupet, L.; Chang, V. Y.; Muller, G.; Williams, J. A. G.; Roussel, C.; Autschbach, J.; Crassous, J. Chem.Commun. 2015, 51, 3754.
58. [58]
  Hellou, N.; Srebro-Hooper, M.; Favereau, L.; Zinna, F.; Caytan, E.; Toupet, L.; Dorcet, V.; Jean, M.; Vanthuyne, N.; Williams, J. A. G.; Di Bari, L.; Autschbach, J.; Crassous, J. Angew. Chem. Int. Ed. 2017, 56, 8236. doi: 10.1002/anie.v56.28
59. [59]
  Shen, Y.; Lu, H.-Y.; Chen, C.-F. Angew. Chem. Int. Ed. 2014, 53, 4648. doi: 10.1002/anie.201400486
60. [60]
  Li, M.; Lu, H.-Y.; Zhang, C.; Shi, L.; Tang, Z.; Chen, C.-F. Chem. Commun. 2016, 52, 9921. doi: 10.1039/C6CC04674F
61. [61]
  He, D.-Q.; Lu, H.-Y.; Li, M.; Chen, C.-F. Chem. Commun. 2017, 53, 6093. doi: 10.1039/C7CC01882G
62. [62]
  Fang, L.; Li, M.; Lin, W.-B.; Shen, Y.; Chen, C.-F. J. Org. Chem. 2017, 82, 7402. doi: 10.1021/acs.joc.7b01087
63. [63]
  Lin, W.-B.; Li, M.; Fang, L.; Shen, Y.; Chen, C.-F. Chem. Asian J. 2017, 12, 86. doi: 10.1002/asia.v12.1
1. [1]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
2. [2]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
3. [3]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
4. [4]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
5. [5]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
6. [6]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
7. [7]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
8. [8]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
9. [9]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
10. [10]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
11. [11]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . Kinetic Resolution Enabled by Photoexcited Chiral Copper Complex-Mediated Alkene E→Z Isomerization: A Comprehensive Chemistry Experiment for Undergraduate Students. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
12. [12]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
13. [13]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
14. [14]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
15. [15]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
16. [16]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
17. [17]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
18. [18]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
19. [19]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
20. [20]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050

Get Citation

PDF

XML

Metrics

PDF Downloads(742)
Abstract views(14250)
HTML views(5537)

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