Citation: WU Nan, HE Zhi-Qun, XU Min, XIAO Wei-Kang. Recent Developments of Azatriphenylene Materials as n-Type Organic Semiconductors[J]. Acta Physico-Chimica Sinica, ;2014, 30(6): 1001-1016. doi: 10.3866/PKU.WHXB201404012 shu

Recent Developments of Azatriphenylene Materials as n-Type Organic Semiconductors

1.
Key Laboratory of Luminescence and Optical Information, Ministry of Education, Institute of Optoelectronic Technology, Beijing Jiaotong University, Beijing 100044, P. R. China

Received Date: 21 January 2014
Available Online: 1 April 2014
Fund Project:

Discotic liquid crystals are a new class of organic electronic materials, and most of these materials display hole-transporting properties. n-Type discotic materials with electro n-transporting properties are rare. Azatriphenylene is one of the most important discotic materials having similar structure to triphenylene derivatives. The introduction of nitrogen atom(s) into the molecular structure of azatriphenylene enhanced its electron affinity properties, making the azatriphenylene derivatives potential n-type organic semiconductors and important materials in terms of their application in optoelectronic devices. This paper reviews recent research progress towards the development of discotic azatriphenylene derivatives, provides discussion on their synthetic methodologies, and accesses their properties as well as their molecular structures such as di-azatriphenylene, tetra-azatriphenylene, and hexa-azatriphenylene. As potential n-type organic semiconductors, the prospective applications of the azatriphenylene materials in optoelectronic devices are explored.
- Discotic liquid crystal,
- Triphenylene,
- Aza-material,
- n-Type organic semiconductor,
- Optoelectronic device
1. [1]
  
  (1) Chandrasekhar, S.; Sadashiva, B.; Suresh, K. Pramana 1977, 9, 471. doi: 10.1007/BF02846252
2. [2]
  (2) Billard, J.; Dubois, J.; Tinh, N. H.; Zann, A. Nouv. J. Chimie 1978, 2, 535.
3. [3]
  (3) Kumar, S. Liquid Crystals 2004, 31, 1037. doi: 10.1080/02678290410001724746
4. [4]
  (4) Kumar, S. Liquid Crystals 2005, 32, 1089. doi: 10.1080/02678290500117415
5. [5]
  (5) Pérez, D.; Guitián, E. Chemical Society Reviews 2004, 33, 274. doi: 10.1039/b305549n
6. [6]
  (6) Mao, H. X.; He, Z. Q.; Zhang, C. X. Chin. J. Org. Chem. 2006, 26, 413. [毛华香, 何志群, 张春秀. 有机化学, 2006, 26, 413.]
7. [7]
  (7) Adam, D.; Closs, F.; Frey, T.; Funhoff, D.; Haarer, D.; Schuhmacher, P.; Siemensmeyer, K. Physical Review Letters 1993, 70, 457. doi: 10.1103/PhysRevLett.70.457
8. [8]
  (8) Adam, D.; Schuhmacher, P.; Simmerer, J.; Hussling, L.; Siemensmeyer, K.; Etzbachi, K.; Ringsdorf, H.; Haarer, D. Nature 1994, 371, 141. doi: 10.1038/371141a0
9. [9]
  (9) Van de Craats, A. M.;Warman, J. M.; de Haas, M. P.; Adam, D.; Simmerer, J.; Haarer, D.; Schuhmacher, P. Advanced Materials 1996, 8, 823. doi: 10.1002/adma.19960081012
10. [10]
  (10) Van de Craats, A. M.;Warman, J. M. Advanced Materials 2001, 13, 130. doi: 10.1002/1521-4095(200101)13:2<130::AID-ADMA130>3.0.CO;2-L
11. [11]
  (11) Warman, J. M.; Van de Craats, A. M. Molecular Crystals and Liquid Crystals 2003, 396, 41. doi: 10.1080/15421400390213186
12. [12]
  (12) Donovan, K.; Kreouzis, T.; Scott, K.; Bunning, J.; Bushby, R.; Boden, N.; Lozman, O.; Movaghar, B. Molecular Crystals and Liquid Crystals 2003, 396, 91. doi: 10.1080/15421400390213221
13. [13]
  (13) Iino, H.; Hanna, J. I.; Jäger, C.; Haarer, D. Molecular Crystals and Liquid Crystals 2005, 436, 217.
14. [14]
  (14) Bayer, A.; Zimmermann, S.;Wendorff, J. Molecular Crystals and Liquid Crystals 2003, 396, 1. doi: 10.1080/15421400390213159
15. [15]
  (15) Lüssem, G.;Wendorff, J. Polymers for Advanced Technologies 1998, 9, 443. doi: 10.1002/(SICI)1099-1581(199807)9:7<443::AID-PAT799>3.0.CO;2-R
16. [16]
  (16) Freudenmann, R.; Behnisch, B.; Hanack, M. J. Mater. Chem. 2001, 11, 1618. doi: 10.1039/b100083g
17. [17]
  (17) Bacher, A.; Bleyl, I.; Erdelen, C. H.; Haarer, D.; Paulus,W.; Schmidt, H.W. Advanced Materials 1997, 9, 1031. doi: 10.1002/adma.19970091307
18. [18]
  (18) Seguy, I.; Destruel, P.; Bock, H. Synthetic Metals 2000, 111, 15.
19. [19]
  (19) Mao, H.; He, Z.;Wang, J.; Zhang, C.; Xie, P.; Zhang, R. Journal of Luminescence 2007, 122, 942.
20. [20]
  (20) Scott, K.; Donovan, K.; Kreouzis, T.; Bunning, J.; Bushby, R.; Boden, N.; Lozman, O. Molecular Crystals and Liquid Crystals 2003, 397, 253. doi: 10.1080/714965610
21. [21]
  (21) Schmidt-Mende, L.; Fechtenktter, A.; Müllen, K.; Moons, E.; Friend, R.; MacKenzie, J. Science 2001, 293, 1119. doi: 10.1126/science.293.5532.1119
22. [22]
  (22) Seguy, I.; Jolinat, P.; Destruel, P.; Farenc, J.; Mamy, R.; Bock, H.; Ip, J.; Nguyen, T. P. Journal of Applied Physics 2001, 89, 5442. doi: 10.1063/1.1365059
23. [23]
  (23) Kumar, S. Current Science-Bangalore 2002, 82, 256.
24. [24]
  (24) Pisula,W.; Menon, A.; Stepputat, M.; Lieberwirth, I.; Kolb, U.; Tracz, A.; Sirringhaus, H.; Pakula, T.; Müllen, K. Advanced Materials 2005, 17, 684. doi: 10.1002/adma.200401171
25. [25]
  (25) Saragi, T. P.; Reichert, T.; Scheffler, A.; Kussler, M.; Salbeck, J. Synthetic Metals 2012, 162, 1572. doi: 10.1016/j.synthmet.2012.07.021
26. [26]
  (26) Forget, S.; Kitzerow, H. S. Liquid Crystals 1997, 23, 919. doi: 10.1080/026782997207867
27. [27]
  (27) Anthony, J. E.; Facchetti, A.; Heeney, M.; Marder, S. R.; Zhan, X. Advanced Materials 2010, 22, 3876. doi: 10.1002/adma.200903628
28. [28]
  (28) Chua, L. L.; Zaumseil, J.; Chang, J. F.; Ou, E. C.W.; Ho, P. K. H.; Sirringhaus, H.; Friend, R. H. Nature 2005, 434, 194. doi: 10.1038/nature03376
29. [29]
  (29) Ando, S.; Murakami, R.; Nishida, J. I.; Tada, H.; Inoue, Y.; Tokito, S.; Yamashita, Y. Journal of the American Chemical Society 2005, 127, 14996. doi: 10.1021/ja055686f
30. [30]
  (30) Tonzola, C. J.; Alam, M. M.; Kaminsky,W.; Jenekhe, S. A. Journal of the American Chemical Society 2003, 125, 13548. doi: 10.1021/ja036314e
31. [31]
  (31) Bao, Z. Advanced Materials 2000, 12, 227. doi: 10.1002/(SICI)1521-4095(200002)12:3<227::AID-ADMA227>3.0.CO;2-U
32. [32]
  (32) Crone, B.; Dodabalapur, A.; Lin, Y. Y.; Filas, R.; Bao, Z.; LaDuca, A.; Sarpeshkar, R.; Katz, H.; Li,W. Nature 2000, 403, 521. doi: 10.1038/35000530
33. [33]
  (33) Briseno, A. L.; Mannsfeld, S. C.; Reese, C.; Hancock, J. M.; Xiong, Y.; Jenekhe, S. A.; Bao, Z.; Xia, Y. Nano Letters 2007, 7, 2847. doi: 10.1021/nl071495u
34. [34]
  (34) Jang, J.; Nam, S.; Chung, D. S.; Kim, S. H.; Yun,W. M.; Park, C. E. Advanced Functional Materials 2010, 20, 2611. doi: 10.1002/adfm.201000383
35. [35]
  (35) Chikamatsu, M.; Taima, T.; Yoshida, Y.; Saito, K.; Yase, K. Applied Physics Letters 2004, 84, 127. doi: 10.1063/1.1637943
36. [36]
  (36) Lee, T.W.; Byun, Y.; Koo, B.W.; Kang, I. N.; Lyu, Y. Y.; Lee, C. H.; Pu, L.; Lee, S. Y. Advanced Materials 2005, 17, 2180. doi: 10.1002/adma.200401672
37. [37]
  (37) Günes, S.; Neugebauer, H.; Sariciftci, N. S. Chemical Reviews 2007, 107, 1324. doi: 10.1021/cr050149z
38. [38]
  (38) Friend, R.; Gymer, R.; Holmes, A.; Burroughes, J.; Marks, R.; Taliani, C.; Bradley, D.; DosSantos, D.; Bredas, J.; Logdlund, M. Nature 1999, 397, 121. doi: 10.1038/16393
39. [39]
  (39) Galán-Mascarós, J. R.; Dunbar, K. R. Chemical Communications 2001, 217.
40. [40]
  (40) Grove, H.; Sletten, J.; Julve, M.; Lloret, F. Journal of the Chemical Society, Dalton Transactions 2001, 1029.
41. [41]
  (41) Marshall, S. R.; Rhein ld, A. L.; Dawe, L. N.; Shum,W.W.; Kitamura, C.; Miller, J. S. Inorganic Chemistry 2002, 41, 3599. doi: 10.1021/ic020176x
42. [42]
  (42) Nasielski-Hinkens, R.; Benedek-Vamos, M.; Maetens, D.; Nasielski, J. Journal of Organometallic Chemistry 1981, 217, 179. doi: 10.1016/S0022-328X(00)85778-2
43. [43]
  (43) Ishi-i, T.; Murakami, K. I.; Imai, Y.; Mataka, S. The Journal of Organic Chemistry 2006, 71, 5752. doi: 10.1021/jo060768n
44. [44]
  (44) Lemaur, V.; da Silva Filho, D. A.; Coropceanu, V.; Lehmann, M.; Geerts, Y.; Piris, J.; Debije, M. G.; Van de Craats, A. M.; Senthilkumar, K.; Siebbeles, L. D. A. Journal of the American Chemical Society 2004, 126, 3271. doi: 10.1021/ja0390956
45. [45]
  (45) Ding, F. J.; Zhao, K. Q. Chemical Research and Application 2006, 18, 795. [丁涪江, 赵可清. 化学研究与应用, 2006, 18, 795.]
46. [46]
  (46) Hu, D.; Cai, J.; Chen, J. R.; Li, Q.; Zhao, K. Q. Chin. Phys. Soc. 2008, 57, 5464. [胡丹, 蔡静, 陈俊蓉, 李权, 赵可清. 物理学报, 2008, 57, 5464.]
47. [47]
  (47) Nan, G. J.; Zheng, R. H.; Shi, Q.; Shuai, Z. G. Acta Phys. -Chim. Sin. 2010, 26, 7. [南广军, 郑仁慧, 史强, 帅志刚. 物理化学学报, 2010, 26, 7.] doi: 10.3866/PKU.WHXB20100120
48. [48]
  (48) pee, H.; Kong, X.; He, Z.; Chambrier, I.; Hughes, D. L.; Tizzard, G. J.; Coles, S. J.; Cammidge, A. N. The Journal of Organic Chemistry 2013, 78, 9505. doi: 10.1021/jo401551c
49. [49]
  (49) Wang, T.; Zhou, E. L. Polyme Bulletin 1993, 1, 33. [王涛, 周恩乐. 高分子通报, 1993, 1, 33.]
50. [50]
  (50) Cammidge, A. N.; Bushby, R. J. Synthesis and Structural Features. In Handbook of Liquid Crystals, Vol. 2B; Demus, D., odby, J.W., Gray, G.W., Spiess, H.W., Vill, V. Eds.;Wiley-VCH:Weinheim, 1998; pp 693-748.
51. [51]
  (51) Zheng, X. P.; He, Z. Q.; Zhang, C. X.;Wang, Y. S. Journal of Functional Materials 2005, 36, 321. [郑效盼, 何志群, 张春秀, 王永生. 功能材料, 2005, 36, 321.]
52. [52]
  (52) Kato, T.; Mizoshita, N.; Kishimoto, K. Angewandte Chemie International Edition 2006, 45, 38. doi: 10.1002/anie.200501384
53. [53]
  (53) Kumar, S. Chemical Society Reviews 2006, 35, 83. doi: 10.1039/b506619k
54. [54]
  (54) Laschat, S.; Baro, A.; Steinke, N.; Giesselmann, F.; Hägele, C.; Scalia, G.; Judele, R.; Kapatsina, E.; Sauer, S.; Schreivogel, A.; Tosoni, M. Angewandte Chemie International Edition 2007, 46,4832. doi: 10.1002/anie.200604203
55. [55]
  (55) Wu, J.; Pisula,W.;Müllen, K. Chemical Reviews 2007, 107, 718. doi: 10.1021/cr068010r
56. [56]
  (56) Wang, X. Z.;Wang, X. F. Materials Review 2009, 23, 93. [王学智, 王秀峰. 材料导报, 2009, 23, 93.]
57. [57]
  (57) Bisoyi, H. K.; Kumar, S. Chemical Society Reviews 2010, 39, 264. doi: 10.1039/b901792p
58. [58]
  (58) Chen, S. S.; Li, T.; Zhao, D. H. Acta Phys. -Chim. Sin. 2010, 26, 1124. [陈树森, 李田, 赵达慧. 物理化学学报, 2010, 26, 1124.] doi: 10.3866/PKU.WHXB20100412
59. [59]
  (59) Kumar, S. Chemistry of Discotic Liquid Crystals, from Monomers to Polymers; CRC Press, Taylor & Francis Group: Boca Raton, 2010.
60. [60]
  (60) Mohr, B.;Wegner, G.; Ohta, K. J. Chem. Soc., Chem. Commun. 1995, 995.
61. [61]
  (61) Foster, E. J.; Babuin, J.; Nguyen, N.;Williams, V. E. Chemical Communications 2004, 2052.
62. [62]
  (62) Kong, X. F.; He, Z. Q.; Xu, M.; Liang, C. J.; Chen, B.; Jing, X. P. Journal of Beijing Jiaotong University 2011, 35, 1. [ 孔翔飞, 何志群, 许敏, 梁春军, 陈博, 荆西平. 北京交通大学学报, 2011, 35, 1.]
63. [63]
  (63) Kong, X.; He, Z.; Xu, M.; Liang, C.; Jing, X. Functional Materials Letters 2011, 4, 345. doi: 10.1142/S1793604711002184
64. [64]
  (64) Terasawa, N.; Monobe, H.; Kiyohara, K.; Shimizu, Y. Chemical Communications 2003, 1678.
65. [65]
  (65) Foster, E. J.; Jones, R. B.; Lavigueur, C.;Williams, V. E. Journal of the American Chemical Society 2006, 128, 8569. doi: 10.1021/ja0613198
66. [66]
  (66) Babuin, J.; Foster, J.;Williams, V. E. Tetrahedron Letters 2003, 44, 7003. doi: 10.1016/S0040-4039(03)01798-2
67. [67]
  (67) Lavigueur, C.; Foster, E. J.;Williams, V. E. Journal of the American Chemical Society 2008, 130, 11791. doi: 10.1021/ja803406k
68. [68]
  (68) Foster, E. J.; Lavigueur, C.; Ke, Y. C.;Williams, V. E. Journal of Materials Chemistry 2005, 15, 4062. doi: 10.1039/b503310a
69. [69]
  (69) Lavigueur, C.; Foster, J. E.;Williams, V. E. Liquid Crystals 2007, 34, 833. doi: 10.1080/02678290701407243
70. [70]
  (70) Sergeyev, S.; Pisula,W.; Geerts, Y. H. Chemical Society Reviews 2007, 36, 1902. doi: 10.1039/b417320c
71. [71]
  (71) Cozzi, F.; Ponzini, F.; Annunziata, R.; Cinquini, M.; Siegel, J. S. Angewandte Chemie International Edition in English 1995, 34, 1019. doi: 10.1002/anie.199510191
72. [72]
  (72) Zhang, L.; Yue, S.; Li, B.; Fan, D. Inorganica Chimica Acta 2012, 384, 225. doi: 10.1016/j.ica.2011.12.002
73. [73]
  (73) Ge, H.;Wei,W.; Shuai, P.; Lei, G.; Qing, S. Journal of Luminescence 2011, 131, 238. doi: 10.1016/j.jlumin.2010.10.004
74. [74]
  (74) Palma, M.; Levin, J.; Lemaur, V.; Liscio, A.; Palermo, V.; Cornil, J.; Geerts, Y.; Lehmann, M.; Samori, P. Advanced Materials 2006, 18, 3313. doi: 10.1002/adma.200601437
75. [75]
  (75) Mahoney, S. J.; Ahmida, M. M.; Kayal, H.; Fox, N.; Shimizu, Y.; Eichhorn, S. H. Journal of Materials Chemistry 2009, 19, 9221. doi: 10.1039/b914290h
76. [76]
  (76) Gao, B.; Xia, D.; Geng, Y.; Cheng, Y.;Wang, L. Tetrahedron Letters 2010, 51, 1919. doi: 10.1016/j.tetlet.2010.02.039
77. [77]
  (77) Gao, B.; Liu, Y.; Geng, Y.; Cheng, Y.;Wang, L.; Jing, X.; Wang, F. Tetrahedron Letters 2009, 50, 1649. doi: 10.1016/j.tetlet.2009.01.126
78. [78]
  (78) Ishi-i, T.; Hirayama, T.; Murakami, K. I.; Tashiro, H.; Thiemann, T.; Kubo, K.; Mori, A.;Yamasaki, S.; Akao, T.; Tsuboyama, A. Langmuir 2005, 21, 1261. doi: 10.1021/la047874+
79. [79]
  (79) Li, J.; He, Z.; pee, H.; Cammidge, A. N. Organic Letters 2010, 12, 472. doi: 10.1021/ol902637z
80. [80]
  (80) Wang, R.; Okajima, T.; Kitamura, F.; Matsumoto, N.; Thiemann, T.; Mataka, S.; Ohsaka, T. The Journal of Physical Chemistry B 2003, 107, 9452. doi: 10.1021/jp0305281
81. [81]
  (81) Wang, R.; Ramaraj, R.; Okajima, T.; Kitamura, F.; Matsumoto, N.; Thiemann, T.; Mataka, S.; Ohsaka, T. Journal of Electroanalytical Chemistry 2004, 567, 85. doi: 10.1016/j.jelechem.2003.12.016
82. [82]
  (82) Ishi-i, T.; Murakami, K. I.; Imai, Y.; Mataka, S. Organic Letters 2005, 7, 3175. doi: 10.1021/ol050919t
83. [83]
  (83) Hirayama, T.; Yamasaki, S.; Ameku, H.; Ishi-i, T.; Thiemann, T.; Mataka, S. Dyes and Pigments 2005, 67, 105. doi: 10.1016/j.dyepig.2004.09.023
84. [84]
  (84) Boden, N.; Bushby, R. J.; Cooke, G.; Lozman, O. R.; Lu, Z. Journal of the American Chemical Society 2001, 123, 7915. doi: 10.1021/ja003443b
85. [85]
  (85) Arikainen, E. O.; Boden, N.; Bushby, R. J.; Lozman, O. R.; Vinter, J. G.;Wood, A. Angewandte Chemie International Edition 2000, 39, 2333. doi: 10.1002/1521-3773(20000703)39:13<2333::AID-ANIE2333>3.0.CO;2-V
86. [86]
  (86) Lozman, O. R.; Bushby, R. J.; Vinter, J. G. Journal of the Chemical Society, Perkin Transactions 2 2001, 1446.
87. [87]
  (87) Oliva, M. M.; Juárez, R.; Ramos, M.; Segura, J. L.; Cleuvenbergen, S. V.; Clays, K.; odson, T., III; Navarrete, J. T. L. P.; Casado, J. The Journal of Physical Chemistry C 2012, 117, 626.
88. [88]
  (88) Cho, B. R.; Lee, S. K.; Kim, K. A.; Son, K. N.; Kang, T. I.; Jeon, S. J. Tetrahedron Letters 1998, 39, 9205. doi: 10.1016/S0040-4039(98)02098-X
89. [89]
  (89) Tao, Z. G.; Zhao, X.; Jiang, X. K.; Li, Z. T. Tetrahedron Letters 2012, 53, 1840. doi: 10.1016/j.tetlet.2012.01.137
90. [90]
  (90) Beeson, J. C.; Fitzgerald, L. J.; Gallucci, J. C.; Gerkin, R. E.; Rademacher, J. T.; Czarnik, A.W. Journal of the American Chemical Society 1994, 116, 4621. doi: 10.1021/ja00090a010
91. [91]
  (91) Cornil, J.; Lemaur, V.; Calbert, J. P.; Brédas, J. L. Advanced Materials 2002, 14, 726. doi: 10.1002/1521-4095(20020517)14:10<726::AID-ADMA726>3.0.CO;2-D
92. [92]
  (92) Reichert, T.; Saragi, T. P. I.; Salbeck, J. RSC Advances 2012, 2, 7388. doi: 10.1039/c2ra20901b
93. [93]
  (93) Lin, H.W.; Lin,W. C.; Chang, J. H.;Wu, C. I. Organic Electronics 2013, 14, 1204. doi: 10.1016/j.orgel.2013.02.011
94. [94]
  (94) Liao, L. S.; Slusarek,W. K.; Hatwar, T. K.; Ricks, M. L.; Comfort, D. L. Advanced Materials 2008, 20, 324. doi: 10.1002/adma.200700454
95. [95]
  (95) Falkenberg, C.; Olthof, S.; Rieger, R.; Baumgarten, M.; Muellen, K.; Leo, K.; Riede, M. Solar Energy Materials and Solar Cells 2011, 95, 927. doi: 10.1016/j.solmat.2010.11.024
96. [96]
  (96) Frank, P.; Koch, N.; Koini, M.; Rieger, R.; Müllen, K.; Resel, R.;Winkler, A. Chemical Physics Letters 2009, 473, 321. doi: 10.1016/j.cplett.2009.04.019
97. [97]
  (97) Jang, S. E.; Lee, J. Y. Synthetic Metals 2011, 161, 40. doi: 10.1016/j.synthmet.2010.10.031
98. [98]
  (98) Furukawa, S.; Okubo, T.; Masaoka, S.; Tanaka, D.; Chang, H. C.; Kitagawa, S. Angewandte Chemie International Edition 2005, 44, 2700. doi: 10.1002/anie.200462962
99. [99]
  (99) Bröker, B.; Hofmann, O.; Rangger, G.; Frank, P.; Blum, R. P.; Rieger, R.; Venema, L.; Vollmer, A.; Müllen, K.; Rabe, J. Physical Review Letters 2010, 104, 246805. doi: 10.1103/PhysRevLett.104.246805
100. [100]
  (100) Frank, P.; Djuric, T.; Koini, M.; Salzmann, I.; Rieger, R.; Müllen, K.; Resel, R.; Koch, N.;Winkler, A. The Journal of Physical Chemistry C 2010, 114, 6650. doi: 10.1021/jp100704v
101. [101]
  (101) Glowatzki, H.; Bröker, B.; Blum, R. P.; Hofmann, O. T.; Vollmer, A.; Rieger, R.; Müllen, K.; Zojer, E.; Rabe, J. R. P.; Koch, N. Nano Letters 2008, 8, 3825. doi: 10.1021/nl8021797
102. [102]
  (102) Perova, T.; Tsvetkov, S.; Vij, J.; Kumar, S. Molecular Crystals and Liquid Crystals 2000, 351, 95. doi: 10.1080/10587250008023257
103. [103]
  (103) Ichimura, K.; Furumi, S.; Morino, S.; Kidowaki, M.; Nakagawa, M.; Ogawa, M.; Nishiura, Y. Advanced Materials 2000, 12, 950. doi: 10.1002/1521-4095(200006)12:13<950::AID-ADMA950>3.0.CO;2-V
104. [104]
  (104) Monobe, H.; Kiyohara, K.; Heya, M.; Awazu, K.; Shimizu, Y. Molecular Crystals and Liquid Crystals 2003, 397, 59. doi: 10.1080/714965596
105. [105]
  (105) Jeon, S. O.; Lee, J. Y. Journal of Industrial and Engineering Chemistry 2012, 18, 661. doi: 10.1016/j.jiec.2011.11.056
106. [106]
  (106) Cho, S. H.; Pyo, S.W.; Suh, M. C. Synthetic Metals 2012, 162, 402. doi: 10.1016/j.synthmet.2011.12.028
107. [107]
  (107) Najafabadi, E.; Knauer, K. A.; Haske,W.; Kippelen, B. Organic Electronics 2013, 14, 1217
108. [108]
  (108) Juárez, R.; Ramos, M. M.; Segura, J. L. Tetrahedron Letters 2007, 48, 8829. doi: 10.1016/j.tetlet.2007.10.069
109. [109]
  (109) Gearba, R. I.; Lehmann, M.; Levin, J.; Ivanov, D. A.; Koch, M. H.; Barbera, J.; Debije, M. G.; Piris, J.; Geerts, Y. H. Advanced Materials 2003, 15, 1614. doi: 10.1002/adma.200305137
110. [110]
  (110) Chang, T. H.;Wu, B. R.; Chiang, M. Y.; Liao, S. C.; Ong, C. W.; Hsu, H. F.; Lin, S. Y. Organic Letters 2005, 7, 4075. doi: 10.1021/ol051231j
111. [111]
  (111) Zhang, X.; Zhao, Q.; Liu, X.; Hu, T.; Han, J.; Ruan,W.; Bu, X. Talanta 2013, 108, 150. doi: 10.1016/j.talanta.2013.02.071
112. [112]
  (112) Skujins, S.;Webb, G. Tetrahedron 1969, 25, 3935. doi: 10.1016/S0040-4020(01)82926-4
113. [113]
  (113) Kestemont, G.; De Halleux, V.; Lehmann, M.; Ivanov, D. A.; Watson, M.; Geerts, Y. H. Chemical Communications 2001, 2074.
114. [114]
  (114) Kitagawa, S.; Masaoka, S. Coordination Chemistry Reviews 2003, 246, 73. doi: 10.1016/S0010-8545(03)00109-7
115. [115]
  (115) Ha, S. D.; Kaafarani, B. R.; Barlow, S.; Marder, S. R.; Kahn, A. The Journal of Physical Chemistry C 2007, 111, 10493. doi: 10.1021/jp0718404
116. [116]
  (116) Lehmann, M.; Kestemont, G.; Gómez Aspe, R.; Buess-Herman, C.; Koch, M. H. J.; Debije,M. G.; Piris, J.; de Haas, M. P.;Warman, J. M.;Watson, M. D.; Lemaur, V.; Cornil, J.; Geerts, Y. H.; Gearba, R.; Ivanov, D. A. Chemistry -A European Journal 2005, 11, 3349. doi: 10.1002/chem.200400586
117. [117]
  (117) Lehmann, M.; Lemaur, V.; Cornil, J.; Brédas, J. L.; ddard, S.; Grizzi, I.; Geerts, Y. Tetrahedron 2004, 60, 3283. doi: 10.1016/j.tet.2004.01.083
118. [118]
  (118) Ong, C.W.; Liao, S. C.; Chang, T. H.; Hsu, H. F. Tetrahedron Letters 2003, 44, 1477. doi: 10.1016/S0040-4039(02)02862-9
119. [119]
  (119) Ong, C.W.; Liao, S. C.; Chang, T. H.; Hsu, H. F. The Journal of Organic Chemistry 2004, 69, 3181. doi: 10.1021/jo035840l
120. [120]
  (120) Yeh, M. C.; Liao, S. C.; Chao, S. H.; Ong, C.W. Tetrahedron 2010, 66, 8888. doi: 10.1016/j.tet.2010.09.064
121. [121]
  (121) Kaafarani, B. R.; Kondo, T.; Yu, J.; Zhang, Q.; Dattilo, D.; Risko, C.; Jones, S. C.; Barlow, S.; Domercq, B.; Amy, F. Journal of the American Chemical Society 2005, 127, 16358.doi: 10.1021/ja0553147
122. [122]
  (122) Ishi-i, T.; Amemori, S.; Okamura, C.; Yanaga, K.; Kuwahara, R.; Mataka, S.; Kamada, K.Tetrahedron 2013, 69, 29. doi: 10.1016/j.tet.2012.10.070
123. [123]
  (123) Ishi-i, T.; Yaguma, K.; Kuwahara, R.; Taguri, Y.; Mataka, S. Organic Letters 2006, 8, 585. doi: 10.1021/ol052779t
124. [124]
  (124) Ishi-i, T.; Hirashima, R.; Tsutsumi, N.; Amemori, S.; Matsuki, S.; Teshima, Y.; Kuwahara, R.; Mataka, S. The Journal of Organic Chemistry 2010, 75, 6858. doi: 10.1021/jo101212d
125. [125]
  (125) Juárez, R.; Oliva, M. M.; Ramos, M.; Segura, J. L.; Alemán, C.; Rodríguez-Ropero, F.; Curcó, D.; Montilla, F.; Coropceanu, V.; Brédas, J. L.; Qi, Y.; Kahn, A.; Ruiz Delgado, M. C.; Casado, J.; LópezNavarrete, J. T. Chemistry-A European Journal 2011, 17, 10312. doi: 10.1002/chem.201101198
126. [126]
  (126) Liu, X. M.; Zhao, Q.; Song,W. C.; Bu, X. H. Chemistry-A European Journal 2012, 18, 2806. doi: 10.1002/chem.201102725
127. [127]
  (127) Klivansky, L. M.; Hanifi, D.; Koshkakaryan, G.; Holycross, D. R.; rski, E. K.;Wu, Q.; Chai, M.; Liu, Y. Chemical Science 2012, 3, 2009. doi: 10.1039/c2sc20241g
128. [128]
  (128) Salomon, E.; Zhang, Q.; Barlow, S.; Marder, S. R.; Kahn, A. Organic Electronics 2008, 9, 944. doi: 10.1016/j.orgel.2008.06.015
129. [129]
  (129) Ha, S. D.; Zhang, Q.; Barlow, S.; Marder, S. R.; Kahn, A. Physical Review B 2008, 77, 085433. doi: 10.1103/PhysRevB.77.085433
130. [130]
  (130) Pieterse, K.; van Hal, P. A.; Kleppinger, R.; Vekemans, J. A.; Janssen, R. A.; Meijer, E. Chemistry of Materials 2001, 13, 2675. doi: 10.1021/cm010181j
131. [131]
  (131) Gao, B.; Zhang, L.; Bai, Q.; Li, Y.; Yang, J.;Wang, L. New Journal of Chemistry 2010, 34, 2735. doi: 10.1039/c0nj00586j
1. [1]
  Yue Wu , Jun Li , Bo Zhang , Yan Yang , Haibo Li , Xian-Xi Zhang . Research on Kinetic and Thermodynamic Transformations of Organic-Inorganic Hybrid Materials for Fluorescent Anti-Counterfeiting Application information: Introducing a Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(6): 390-399. doi: 10.3866/PKU.DXHX202403028
2. [2]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
3. [3]
  Xiaofang DONG , Yue YANG , Shen WANG , Xiaofang HAO , Yuxia WANG , Peng CHENG . Research progress of conductive metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 14-34. doi: 10.11862/CJIC.20240388
4. [4]
  .
  CCS Chemistry 综述推荐│绿色氧化新思路：光/电催化助力有机物高效升级
  . CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.
5. [5]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
6. [6]
  Wei HE , Jing XI , Tianpei HE , Na CHEN , Quan YUAN . Application of solar-driven inorganic semiconductor-microbe hybrids in carbon dioxide fixation and biomanufacturing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 35-44. doi: 10.11862/CJIC.20240364
7. [7]
  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
8. [8]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
9. [9]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
10. [10]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
11. [11]
  Mengzhen JIANG , Qian WANG , Junfeng BAI . Research progress on low-cost ligand-based metal-organic frameworks for carbon dioxide capture from industrial flue gas. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 1-13. doi: 10.11862/CJIC.20240355
12. [12]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
13. [13]
  Shengbiao Zheng , Liang Li , Nini Zhang , Ruimin Bao , Ruizhang Hu , Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096
14. [14]
  Chenye An , Abiduweili Sikandaier , Xue Guo , Yukun Zhu , Hua Tang , Dongjiang Yang . 红磷纳米颗粒嵌入花状CeO₂分级S型异质结高效光催化产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2405019-. doi: 10.3866/PKU.WHXB202405019
15. [15]
  Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO₄/g-C₃N₄ S-Scheme Heterojunction with Nitrogen Defect for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002
16. [16]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
17. [17]
  Fan Wu , Wenchang Tian , Jin Liu , Qiuting Zhang , YanHui Zhong , Zian Lin . Core-Shell Structured Covalent Organic Framework-Coated Silica Microspheres as Mixed-Mode Stationary Phase for High Performance Liquid Chromatography. University Chemistry, 2024, 39(11): 319-326. doi: 10.12461/PKU.DXHX202403031
18. [18]
  Zhaomei LIU , Wenshi ZHONG , Jiaxin LI , Gengshen HU . Preparation of nitrogen-doped porous carbons with ultra-high surface areas for high-performance supercapacitors. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 677-685. doi: 10.11862/CJIC.20230404
19. [19]
  Zhuo Wang , Xue Bai , Kexin Zhang , Hongzhi Wang , Jiabao Dong , Yuan Gao , Bin Zhao . MOF模板法合成氮掺杂碳材料用于增强电化学钠离子储存和去除. Acta Physico-Chimica Sinica, 2025, 41(3): 2405002-. doi: 10.3866/PKU.WHXB202405002
20. [20]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105

Get Citation

PDF

XML

Metrics

PDF Downloads(836)
Abstract views(1053)
HTML views(77)

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