Citation: HE You-Zhou, LIU Yun, LIU Peng, FENG Wen, YUAN Li-Hua. Self-Assembly of Vesicles from Oli aramide Based on Multiple Hydrogen Bonds[J]. Acta Physico-Chimica Sinica, ;2014, 30(8): 1501-1508. doi: 10.3866/PKU.WHXB201406122
-
Six-hydrogen-bonded oli aramide heteroduplexes demonstrate extremely high sequencespecificity and tunable stability during their self-assembly. The self-assembly behavior of molecular oli aramide 1 arrayed in a DADDAD-DADDAD sequence and that in the presence of oli aramide 2 with an ADAADAADAADA sequence were examined using multiple techniques, including scanning electron microscopy (SEM), transmission electron microscopy (TEM), and dynamic light scattering (DLS). Results from these experiments indicate that 1 can self-assemble to vesicles with uniform shapes in both tetrahydrofuran/methanol (V/V, 85/15) and acetone, the size of which increased with an increase in solution concentration. Upon addition of the corresponding complementary 2, the vesicles turned into solid balls. Fluorescence microscopy experiments revealed that the vesicles were able to encapsulate the fluorescence molecules (Rhodamine B). With further modification of molecular structures, these vesicles may hold potential for applications as drug carrier as well as in controlled-release technology.
-
Keywords:
-
Self-assembly
, - Vesicle,
- Oli aramide,
- Hydrogen bond,
- Molecular duplex
-
-
-
[1]
(1) Graff, A.; Sauer, M.; Gelder, P. V.; Meier,W. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 5064. doi: 10.1073/pnas.062654499
-
[2]
(2) Stoenescu, R.; Meier,W. Chem. Commun. 2002, 3016.
-
[3]
(3) Wang, Y. Y.; Hua,W.; Liu, T. Q. Acta Phys. -Chim. Sin. 2011, 27, 1907. [王元有, 华伟, 刘天晴. 物理化学学报, 2011, 27, 1907.] doi: 10.3866/PKU.WHXB20110822
-
[4]
(4) Stanish, I.; Lowy, D. A.; Hung, C.W.; Singh, A. Adv. Mater. 2005, 17, 1194.
-
[5]
(5) Yan, Q.; Yuan, J. Y.; Cai, Z. N.; Xin, Y.; Kang, Y.; Yin, Y.W. J. Am. Chem. Soc. 2010, 132, 9268. doi: 10.1021/ja1027502
-
[6]
(6) Yan, Q.; Zhou, R.; Fu, C. K.; Zhang, H. J.; Yin, Y.W.; Yuan, J. Y. Angew. Chem., Int. Edit. 2011, 50, 4923. doi: 10.1002/anie.v50.21
-
[7]
(7) Discher, D. E.; Eisenberg, A. Science 2002, 297, 967. doi: 10.1126/science.1074972
-
[8]
(8) Jones, R. A. L. Nat. Mater. 2004, 3, 209. doi: 10.1038/nmat1109
-
[9]
(9) Duan, Q. P.; Cao, Y.; Li, Y.; Hu, X. Y.; Xiao, T. X.; Lin, C.; Pan, Y.;Wang, L. Y. J. Am. Chem. Soc. 2013, 135, 10542. doi: 10.1021/ja405014r
-
[10]
(10) Li, S.; Qiu, Y. Q.; Zhang, S. H.; Gao, Y. H. Acta Phys. -Chim. Sin. 2011, 27, 2167. [李爽, 邱玉琴, 张锁慧, 高云华. 物理化学学报, 2011, 27, 2167.] doi: 10.3866/PKU.WHXB20110833
-
[11]
(11) Menger, F. M.; Gabrielson, K. D. Angew. Chem. Int. Edit. 1995, 34, 2091.
-
[12]
(12) Moss, R. A.; Bizzi tti, G. O. J. Am. Chem. Soc. 1981, 103, 6512. doi: 10.1021/ja00411a049
-
[13]
(13) Zhao, G. X.; Huang, J. B. Acta Phys. -Chim. Sin. 1992, 8, 583. [赵国玺, 黄建滨. 物理化学学报, 1992, 8, 583.] doi: 10.3866/PKU.WHXB19920503
-
[14]
(14) Discher, B. M.;Won, Y. Y.; Ege, D. S.; Lee, J. C. M.; Bates, F. S.; Discher, D. E.; Hammer, D. A. Science 1999, 284, 1143. doi: 10.1126/science.284.5417.1143
-
[15]
(15) Lee, M.; Lee, S. J.; Jiang, L. H. J. Am. Chem. Soc. 2004, 126, 12724. doi: 10.1021/ja045918v
-
[16]
(16) Guan, B.; Jiang, M.; Yang, X.; Liang, Q.; Chen, Y. Soft Matter 2008, 4, 1393. doi: 10.1039/b805312j
-
[17]
(17) Kim, K.; Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, D.; Kim, J. Chem. Soc. Rev. 2007, 36, 267. doi: 10.1039/b603088m
-
[18]
(18) Ravoo, B. J.; Darcy, R. Angew. Chem. Int. Edit. 2000, 39, 4324.
-
[19]
(19) Lim, C.W.; Crespo-Biel, O.; Stuart, M. C. A.; Reinhoudt, D. N.; Huskens, J.; Ravoo, B. J. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 6986. doi: 10.1073/pnas.0611123104
-
[20]
(20) Zhang, K. D.; Zhou, T. Y.; Zhao, X.; Jiang, X. K.; Li, Z. T. Langmuir 2012, 28, 14839.
-
[21]
(21) Xu, Y. X.;Wang, G. T.; Zhao, X.; Jiang, X. K.; Li, Z. T. Langmuir 2009, 25, 2684. doi: 10.1021/la8034243
-
[22]
(22) Xu, Y. X.;Wang, G. T.; Zhao, X.; Jiang, X. K.; Li, Z. T. Soft Matter 2010, 6, 1246. doi: 10.1039/b917576h
-
[23]
(23) Du, P.;Wang, G. T.; Zhao, X.; Li, G. Y.; Jiang, X. K.; Li, Z. T. Tetrahedron Lett. 2010, 51, 188. doi: 10.1016/j.tetlet.2009.10.115
-
[24]
(24) ng, B. Accounts Chem. Res. 2012, 45, 2077. doi: 10.1021/ar300007k
-
[25]
(25) Li, M. F.; Yamato, K.; Ferguson, J. S.; ng, B. J. Am. Chem. Soc. 2006, 128, 12628. doi: 10.1021/ja064515n
-
[26]
(26) Li, M. F.; Yamato, K.; Ferguson, J. S.; Singarapu, K. K.; Szyperski, T.; ng, B. J. Am. Chem. Soc. 2008, 130, 491. doi: 10.1021/ja072567m
-
[27]
(27) Yuan, L. H.; Zhang, P. H.; Feng,W.; ng, B. Curr. Org. Chem. 2011, 15, 1250. doi: 10.2174/138527211795378236
-
[28]
(28) Yang, X.W.; Hua, F. J.; Yamato, K.; Ruckenstein, E.; ng, B.; Kim,W.; Ryu, C. Y. Angew. Chem. Int. Edit. 2004, 43, 6471.
-
[29]
(29) Yang, X.W.; ng, B. Angew. Chem. Int. Edit. 2005, 44, 1352.
-
[30]
(30) Cao, R. K.; Zhou, J. J.;Wang,W.; Feng,W.; Li, X. H.; Zhang, P. H.; Deng, P. C.; Yuan, L. H.; ng, B. Org. Lett. 2010, 12, 2958. doi: 10.1021/ol100953e
-
[31]
(31) Zhang, P. H.; Chu, H. Z.; Li, X. H.; Feng,W.; Deng, P. C.; Yuan, L. H.; ng, B. Org. Lett. 2011, 13, 54. doi: 10.1021/ol102522m
-
[32]
(32) Zeng, J. S.;Wang,W.; Deng, P. C.; Feng,W.; Zhou, J. J.; Yang, Y. Y.; Yuan, L. H.; Yamato, K.; ng, B. Org. Lett. 2011, 13, 3798. doi: 10.1021/ol201282d
-
[33]
(33) Pan, X. S.; Chen, C.; Peng, J.; Yang, Y. A.;Wang, Y. H.; Feng, W.; Deng, P. C.; Yuan, L. H. Chem. Commun. 2012, 48, 9510. doi: 10.1039/c2cc35004a
-
[34]
(34) Li, X. H.; Fang, Y. Y.; Deng, P. C.; Hu, J. C.; Li, T.; Feng,W.; Yuan, L. H. Org. Lett. 2011, 13, 4628. doi: 10.1021/ol2018455
-
[35]
(35) Li, X. H.; Jia, Y. M.; Ren, Y.;Wang, Y. J.; Hu, J. C.; Ma, T.; Feng,W.; Yuan, L. H. Org. Biomol. Chem. 2013, 11, 6975. doi: 10.1039/c3ob40998h
-
[36]
(36) Liu, Y.; He, Y. Z.; Yuan, L. H.; Feng,W. Acta Phys. -Chim. Sin. 2011, 27, 918. [刘云, 贺有周, 袁立华, 冯文. 物理化学学报, 2011, 27, 918.] doi: 10.3866/PKU.WHXB20110403
-
[37]
(37) Jin, Y. D.; Liu, Y.; Yang, Y. A.; Zhang, D.; Dan, G. P.; Du, J.; Yuan, L. H.; Feng,W. Chin. J. Org. Chem. 2011, 31, 1864. [金永东, 刘云, 杨永安, 张东, 但贵萍, 杜鹃, 袁立华, 冯文. 有机化学, 2011, 31, 1864.]
-
[38]
(38) Zeng, H. Q.; Miller, R. S.; Flowers, R. A.; ng, B. J. Am. Chem. Soc. 2000, 122, 2635. doi: 10.1021/ja9942742
-
[39]
(39) Balakrishnan, K.; Datar, A.; Naddo, T.; Huang, J. L.; Oitker, R.; Yen, M.; Zhao, J. C.; Zang, L. J. Am. Chem. Soc. 2006, 128, 7390. doi: 10.1021/ja061810z
-
[1]
-
-
[1]
Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
-
[2]
Shuyu Liu , Xiaomin Sun , Bohan Song , Gaofeng Zeng , Bingbing Du , Chongshen Guo , Cong Wang , Lei Wang . Design and Fabrication of Phospholipid-Vesicle-based Artificial Cells towards Biomedical Applications. University Chemistry, 2024, 39(11): 182-188. doi: 10.12461/PKU.DXHX202404113
-
[3]
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
-
[4]
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
-
[5]
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
-
[6]
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
-
[7]
Fengqiao Bi , Jun Wang , Dongmei Yang . Specialized Experimental Design for Chemistry Majors in the Context of “Dual Carbon”: Taking the Assembly and Performance Evaluation of Zinc-Air Fuel Batteries as an Example. University Chemistry, 2024, 39(4): 198-205. doi: 10.3866/PKU.DXHX202311069
-
[8]
Hao Wu , Zhen Liu , Dachang Bai . 1H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
-
[9]
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
-
[10]
Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD+: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027
-
[11]
Hong Zheng , Xin Peng , Chunwang Yi . The Tale of Caprolactam Cyclic Oligomers: The Ever-changing Life of “Princess Cyclo”. University Chemistry, 2024, 39(9): 40-47. doi: 10.12461/PKU.DXHX202403058
-
[12]
Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
-
[13]
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
-
[14]
Yong Shu , Xing Chen , Sai Duan , Rongzhen Liao . How to Determine the Equilibrium Bond Distance of Homonuclear Diatomic Molecules: A Case Study of H2. University Chemistry, 2024, 39(7): 386-393. doi: 10.3866/PKU.DXHX202310102
-
[15]
Laiying Zhang , Yinghuan Wu , Yazi Yu , Yecheng Xu , Haojie Zhang , Weitai Wu . Innovation and Practice of Polymer Chemistry Experiment Teaching for Non-Polymer Major Students of Chemistry: Taking the Synthesis, Solution Property, Optical Performance and Application of Thermo-Sensitive Polymers as an Example. University Chemistry, 2024, 39(4): 213-220. doi: 10.3866/PKU.DXHX202310126
-
[16]
Yang YANG , Pengcheng LI , Zhan SHU , Nengrong TU , Zonghua WANG . Plasmon-enhanced upconversion luminescence and application of molecular detection. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 877-884. doi: 10.11862/CJIC.20230440
-
[17]
Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
-
[18]
Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
-
[19]
Shule Liu . Application of SPC/E Water Model in Molecular Dynamics Teaching Experiments. University Chemistry, 2024, 39(4): 338-342. doi: 10.3866/PKU.DXHX202310029
-
[20]
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
-
[1]
Metrics
- PDF Downloads(550)
- Abstract views(610)
- HTML views(5)