Citation:
LUO Xu-Zhong, WANG Qiong, ZHONG Jin-Lian, PAN Hong, CHEN Zhi-Xing. Synthesis of π-Conjugated Triphenylbenzene Derivatives and Their Gelling Property[J]. Acta Physico-Chimica Sinica,
;2011, 27(07): 1719-1724.
doi:
10.3866/PKU.WHXB20110720
-
A series of discotic molecules containing triphenylbenzene group and three monochains were synthesized and their self-assembly properties were studied. These derivatives formed stable gels in many low polarity organic solvents. The lamellar and fibrous aggregate morphologies of the xerogels and the layered structure of the gel aggregates were studied by scanning electron microscopy (SEM) and small angle X-ray diffraction (SA-XRD), respectively. Fourier transform infrared (FT-IR) spectroscopy and UV-Vis absorption spectroscopy revealed that the hydrogen bonding and π-π interactions were the main driving force for the formation of a self-assembled gel. During gel formation, the gelator molecules self-assemble into ordered lamellar aggregates in organic solvents through a π-π conjugation stacking effect and hydrogen bonding. The ordered lamellar aggregates are juxtaposed and interlocked by van der Waals interactions to form sheet-like structure or fiber superstructure and finally immobilize into the organic liquids.
-
-
-
[1]
(1) Sangeetha, N. M.; Maitra, U. Chem. Soc. Rev. 2005, 34, 821.
-
[2]
(2) Gronwald, O.; Shinkai, S. Chem. Eur. J. 2001, 7, 4329.
-
[3]
(3) Wong, G. C. L.; Tang, J. X.; Lin, A.; Li, Y.; Janmey, P. A.; Safinya, C. R. Science 2000, 288, 2035.
-
[4]
(4) Hwang, I.; Jeon,W. S.; Kim, H. J.; Kim, D.; Kim, H.; Selvapalam, N.; Fujita, N.; Shinkai, S.; Kim, K. Angew. Chem. Int. Edit. 2007, 46, 210.
-
[5]
(5) Bhogala, B. R.; Captain, B.; Parthasarathy, A.; Ramamurthy, V. J. Am. Chem. Soc. 2010, 132, 13434.
-
[6]
(6) Shen, L. Y.; Chen, X. Z.; Yu, H. T.; Liang, G. Chin. J. Org. Chem. 2009, 29 (3), 321. [沈利英, 陈肖卓, 于海涛, 梁刚. 有机化学, 2009, 29 (3), 321.]
-
[7]
(7) Bommel, K. J. C. V.; Pol, C. V. D.; Muizebelt, I.; Friggeri, A.; Heeres, A.; Meetsma, A.; Feringa, B. L.; Esch, J.V. Angew. Chem. Int. Edit. 2004, 43, 1663.
-
[8]
(8) Gestel, J. V.; Palmans, A. R. A.; Titulaer, B.; Vekemans, J. A. J. M.; Meijer, E.W. J. Am. Chem. Soc. 2005, 127, 5490.
-
[9]
(9) Bao, C. Y.; Lu, R.; Xue, P. C.; Jin, M.; Tan, C. H.; Xu, T. H.; Liu, G. F.; Zhao, Y. Y. Chem. Eur. J. 2006, 12, 3287.
-
[10]
(10) Elmorsyfa, S. S.; Pelter, B.; Smtthb, K. Tetrahedron Lett. 1991, 32 (33), 4175.
-
[11]
(11) Luo, X. Z.; Li, Z. F.; Xiao,W.;Wang, Q.; Zhong, J. L. J. Colloid Interface Sci. 2009, 336, 803.
-
[12]
(12) Huang, X. T.; Erech, P.; Raghavan, S. R.;Weiss, R. G. J. Am. Chem. Soc. 2005, 127, 4336.
-
[13]
(13) Jung, J.; Ono, Y.; Shinkai, S. Angew. Chem. Int. Edit. 2000, 39, 1862.
-
[14]
(14) Liang, Y. Q.; Jiang, Y. T.; Tian, Y. C. Acta Phys. -Chim. Sin. 1991, 7 (1), 72. [梁映秋, 姜玉涛, 田永池. 物理化学学报, 1991, 7 (1), 72.]
-
[15]
(15) Fujimoto, Y.; Ozaki, Y.; Kato, T.; Matsumoto, N.; Iriyama, K. Chem. Phys. Lett. 1992, 196, 347.
-
[16]
(16) Clegg, R. S.; Hutchison, J. E. Langmuir 1996, 12, 5239.
- [17]
-
[18]
(18) Shitakawa, M.; Kawano, S.; Fujita, N.; Sada, K.; Shinkai, S. J. Org. Chem. 2003, 68, 5037.
-
[19]
(19) Kadam, J.; Faul, C. F. J.; Scherf, U. Chem. Mater. 2004, 16, 3867.
-
[20]
(20) Jung, J. H.; John, G.; Yoshida, K.; Shimizu, T. J. Am. Chem. Soc. 2002, 124, 10674.
-
[21]
(21) Jung, J. H.; Shinkai, S.; Shimizu, T. Chem. Eur. J. 2002, 8, 2684.
-
[22]
(22) Otsumi, E.; Kamaras, P.;Weiss, R. G. Angew. Chem. Int. Edit. 1996, 35, 1324.
-
[1]
-
-
-
[1]
Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
-
[2]
Ruoxi Sun , Yiqian Xu , Shaoru Rong , Chunmiao Han , Hui Xu . The Enchanting Collision of Light and Time Magic: Exploring the Footprints of Long Afterglow Lifetime. University Chemistry, 2024, 39(5): 90-97. doi: 10.3866/PKU.DXHX202310001
-
[3]
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
-
[4]
Yinglian LI , Chengcheng ZHANG , Xinyu ZHANG , Xinyi WANG . Spin crossover in [Co(pytpy)2]2+ complexes modified by organosulfonate anions. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1162-1172. doi: 10.11862/CJIC.20240087
-
[5]
Huiying Xu , Minghui Liang , Zhi Zhou , Hui Gao , Wei Yi . Application of Quantum Chemistry Computation and Visual Analysis in Teaching of Weak Interactions. University Chemistry, 2025, 40(3): 199-205. doi: 10.12461/PKU.DXHX202407011
-
[6]
Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
-
[7]
Wenjian Zhang , Mengxin Fan , Wenwen Fei , Wei Bai . Cultivation of Critical Thinking Ability: Based on RAFT Polymerization-Induced Self-Assembly. University Chemistry, 2025, 40(4): 108-112. doi: 10.12461/PKU.DXHX202406099
-
[8]
Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
-
[9]
Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd6(L)4]8+-type macrocyclic complexes for fluorescent sensing of HSO3-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
-
[10]
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
-
[11]
Lina Feng , Guoyu Jiang , Xiaoxia Jian , Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171
-
[12]
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
-
[13]
Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
-
[14]
Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
-
[15]
Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
-
[16]
Jian Jin , Jing Cheng , Xueping Yang . Integration Practice of Organic Chemistry Experiment and Safety Education: Taking the Synthesis of Triphenylmethanol as an Example. University Chemistry, 2024, 39(3): 345-350. doi: 10.3866/PKU.DXHX202309010
-
[17]
Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
-
[18]
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
-
[19]
Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO2 reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
-
[20]
Shasha Ma , Zujin Yang , Jianyong Zhang . Facile Synthesis of FeBTC Metal-Organic Gel and Its Adsorption of Cr2O72−: A Physical Chemistry Innovation Experiment. University Chemistry, 2024, 39(8): 314-323. doi: 10.3866/PKU.DXHX202401008
-
[1]
Metrics
- PDF Downloads(1019)
- Abstract views(2457)
- HTML views(5)