Supramolecular Gels Formation from N,N',N"-Tris(4-pyridyl)trimesic Amide Induced by Water

doi:10.6023/A15050321

Acta Chim. Sinica ›› 2015, Vol. 73 ›› Issue (10): 1031-1037.DOI: 10.6023/A15050321 Previous Articles Next Articles

Article

水诱导N,N',N"-三(4-吡啶基)-均三苯甲酰胺形成超分子凝胶研究

罗海清, 刘启昊, 朱万财, 王科军, 罗序中

赣南师范学院化学化工学院赣州 341000

投稿日期:2015-05-10 发布日期:2015-07-23
通讯作者: 王科军, 罗序中 E-mail:wangkejun@sina.com; luoxuzhong@hotmail.com
基金资助:
项目受国家自然科学基金(No.51268002)、江西省自然科学基金(Nos.20142BCB22007,20143ACB20009)、江西省教育厅项目(No.KJLD14080)及江西省“赣鄱英才555工程”资助.

Supramolecular Gels Formation from N,N',N"-Tris(4-pyridyl)trimesic Amide Induced by Water

Luo Haiqing, Liu Qihao, Zhu Wancai, Wang Kejun, Luo Xuzhong

Department of Chemistry & Chemical Engineering, Gannan Normal University, Ganzhou 341000

Received:2015-05-10 Published:2015-07-23
Supported by:
Project supported by the National Natural Science Foundation of China (No. 51268002), the Natural Science Foundation of Jiangxi Province (Nos. 20142BCB22007, 20143ACB20009), the Natural Science Foundation of Jiangxi Province (No. KJLD14080), and the “Gan Po 555 Engineering Excellence” of Jiangxi Province, China.

N,N',N"-Tris(4-pyridyl)trimesic amide (4-btapa) was synthesized by chemical modification using 4-aminopyridine to benezene-1,3,5-tricarboxylic acid. The gelating ability of 4-btapa to different solvents and the effect of pH on gelating ability were studied in detail. The results indicated that a stable gel was obtained by adding a certain amount of water to a 4-btapa DMSO solution at room temperature. While adding a certain amount of water to solutions of 4-btapa in DMF, THF, methanol and so on, respectively, only flow turbid liquids with large viscosity were obtained. Upon heating the obtained turbid liquids to clear solutions and cooling them at room temperature, stable gels were also obtained. The structures of the aggregates in the gels were investigated using Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR) spectroscopy, small angle X-ray scattering (SAXS) and scanning electron microscopy (SEM). The result of SEM shows that the 4-btapa can form fibrous self-assembly aggregates in different aqueous solvent, while 4-btapa shows the fiber cluster structure at pH=3.0 water-ethanol system, which is different from regular fibrous aggregate in pH=7.0, suggesting that the pH can affect the aggregation morphology of gelators. The results of nuclear magnetic resonance and infrared spectroscopy revealed that the molecular hydrogen bonds of N—H…Py and aromatic π-π stacking interactions were formed in gel state and water was a part of the gel. From the above observation and analysis of FT-IR, ¹H-NMR and XRD results, we can suggest the self-assembly arrangement of 4-btapa in gel state.

Key words: water induced, supermolecular gel, N,N',N"-tris(4-pyridyl)trimesic amide, self-assembly

Cite this article

Luo Haiqing, Liu Qihao, Zhu Wancai, Wang Kejun, Luo Xuzhong. Supramolecular Gels Formation from N,N',N"-Tris(4-pyridyl)trimesic Amide Induced by Water[J]. Acta Chim. Sinica, 2015, 73(10): 1031-1037.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Tokuyama, H.; Iwama, T. Langmuir 2007, 23, 13104.

[2] Estroff, L. A.; Hamilton, A. D. Chem. Rev. 2004, 4, 1201.

[3] Sun, S.; Liu, J.; Gao, D.; He, P. L.; Fang, Y. Acta Chim. Sinica 2010, 68, 1174. (孙松, 刘静, 高迪, 何盼丽, 房喻, 化学学报, 2010, 68, 1174.)

[4] Shao, Y.; Li, C.; Zhou, X.; Chen, P.; Yang, Z. Q.; Li, Z. B.; Liu, D. S. Acta Chim. Sinica 2015, 73, 815. (邵昱, 李闯, 周旭, 陈平, 杨忠强, 李志波, 刘冬生, 化学学报, 2015, 73, 815.)

[5] Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133.

[6] Zhang, Y. L.; Yang, B.; Xu, L. X.; Zhang, X. Y.; Tao, L.; Wei, Y. Acta Chim. Sinica 2013, 71, 485. (张亚玲, 杨斌, 许亮鑫, 张小勇, 陶磊, 危岩, 化学学报, 2013, 71, 485.)

[7] Liu, S. L.; Zhou, Y. G.; Chen, F. H.; Zhu, S. J.; Su, F. Acta Chim. Sinica 2015, 73, 47. (刘水莲, 周洋, 陈福花, 朱寿进, 宿烽, 李速明, 化学学报, 2015, 73, 47.)

[8] Shen, L. Y.; Chen, X. Z.; Yu, H. T.; Liang, G. Chin. J. Org. Chem. 2009, 29, 321. (沈利英, 陈肖卓, 于海涛, 梁刚, 有机化学, 2009, 29, 321.)

[9] Haines, S. R.; Harrison, R. G. Chem. Commun. 2002, 2846.
[10] Li, Y. G.; Liu, K. Q.; Liu, J.; Peng, J. X.; Feng, X. L.; Fang, Y. Langmuir 2006, 22, 7016.
[11] Shome, A.; Debnath, S.; Das, P. K. Langmuir 2008, 24, 4280.
[12] Luo, X. Z.; Deng, J. H.; Zhong, J. L.; Liu, H. J.; Wang, K. J.; Zhong, D. C. J. Am. Chem. Soc. 2013, 135, 11684.
[13] Fu, X. J.; Yang, Y. J. J. Colloid Interface Sci. 2007, 315, 376.
[14] Huang, X. T.; Erech, P.; Raghavan, S. R.; Weiss, R. G. J. Am. Chem. Soc. 2005, 127, 4336.
[15] Luo, X. Z.; Wang, Q.; Zhong, J. L.; Pan, H.; Chen, Z. X. Acta Phys. Chim. Sin. 2011, 27, 1719. (罗序中, 王琼, 钟金莲, 潘虹, 陈志兴. 物理化学学报, 2011, 27, 1719.)
[16] Liang, Y. Q.; Jiang, Y. T.; Tian, Y. C. Acta Phys. Chim. Sin. 1991, 7, 72. (梁映秋, 姜玉涛, 田永驰, 物理化学学报, 1991, 7, 72.)
[17] Shi, N.; Dong, H.; Yin, G.; Xu, Z.; Li, S. H. Adv. Funct. Mater. 2007, 17, 1837.
[18] Jung, J. H.; Shinkai, S.; Shimizu, T. Chem. Eur. J. 2002, 8, 2684.
[19] Snip, E.; Shinkai, S.; Reinhoudt, D. N. Tetrahedron Lett. 2001, 42, 2153.
[20] Bhattacharya, S.; Basit, H. Chem. Eur. J. 2008, 14, 6534.
[21] Zhou, S. L.; Matsumoto, S.; Tian, H. D.; Yamane, H.; Ojida, A.; Kiyonaka, S.; Hamachi, I. Chem. Eur. J. 2005, 11, 1130.
[22] Kiyonaka, S.; Zhou, S. L.; Hamachi, I. Supramol. Chem. 2003, 15, 521.
[23] Kiyonaka, S.; Sugiyasu, K.; Shinkai, S.; Hamachi, I. J. Am. Chem. Soc. 2002, 124, 10954.
[24] de Loos, M.; Feringa, B. L. Tetrahedron 2007, 63, 7285.
[25] Hasegawa, S.; Kitagawa, S. J. Am. Chem. Soc. 2007, 129, 2607.

水诱导N,N',N"-三(4-吡啶基)-均三苯甲酰胺形成超分子凝胶研究

Supramolecular Gels Formation from N,N',N"-Tris(4-pyridyl)trimesic Amide Induced by Water

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Liwei Hu, Xianhu Liu, Chuntai Liu, Yanlin Song, Mingzhu Li. Self-assembly Fabrication and Applications of Photonic Crystal Structure Color Materials^★ [J]. Acta Chimica Sinica, 2023, 81(7): 809-819.
[2]	Lanying Li, Qing Tao, Yanli Wen, Lele Wang, Ruiyan Guo, Gang Liu, Xiaolei Zuo. Poly-adenine-based DNA Probes and Their Applications in Biosensors^★ [J]. Acta Chimica Sinica, 2023, 81(6): 681-690.
[3]	Xu Pu, Zejuan Li, Junqiu Shi, Yunqing Zhu, Jianzhong Du. Recent Advances in Organ-Targeting Polymeric Delivery Vectors for Nucleic Acids^★ [J]. Acta Chimica Sinica, 2023, 81(10): 1438-1446.
[4]	Jamshid Kadirkhanov, Feng Zhong, Wenjian Zhang, Chunyan Hong. Preparation of Multi-chambered Vesicles by Polymerization-induced Self-assembly and the Influence of Solvophilic Fragments in the Core-forming Blocks [J]. Acta Chimica Sinica, 2022, 80(7): 913-920.
[5]	Zhiqin Wang, Bo Xiang, Xiaoyu Huang, Guolin Lu. Effect of Phosphotungstic Acid on Self-seeding of Oligo(p-phenylenevinylene)-b-poly(2-vinylpyridine)^※ [J]. Acta Chimica Sinica, 2022, 80(3): 297-302.
[6]	Dong Yin, Hongyi Shang, Wenhao Yu, Shikai Xiang, Ping Hu, Keqing Zhao, Chun Feng, Biqin Wang. Synthesis, Mesomorphism and Gelation Properties of Triazole-Modified Triphenylene 2,3-Dicarboxylic Esters and 2,3-Dicarboxyimides [J]. Acta Chimica Sinica, 2022, 80(10): 1376-1384.
[7]	Yanmei Jin, Ye Meng, Yuan Li, Jianhua Shi, Lei Deng. Supramolecular Self-assembly of Symmetric Dicyclohexanocucurbit[6]uril and Nicotinic Hydrazide [J]. Acta Chimica Sinica, 2022, 80(1): 44-48.
[8]	Xusheng Wang, Xu Yang, Chunhui Chen, Hongfang Li, Yuanbiao Huang, Rong Cao. Graphene Quantum Dots Supported on Fe-based Metal-Organic Frameworks for Efficient Photocatalytic CO₂ Reduction^※ [J]. Acta Chimica Sinica, 2022, 80(1): 22-28.
[9]	Weihua Li. “Bridge” Makes Differences to the Self-assembly of Block Copolymers [J]. Acta Chimica Sinica, 2021, 79(2): 133-138.
[10]	Zhao Jingjing, Zhang Zhengzhong, Chen Xiaolang, Wang Bei, Deng Jinyuan, Zhang Dieqing, Li Hexing. Microwave-induced Assembly of CuS@MoS₂ Core-shell Nanotubes and Study on Their Photocatalytic Fenton-like Reactions [J]. Acta Chimica Sinica, 2020, 78(9): 961-967.
[11]	Jiang Jinhui, Zhu Yunqing, Du Jianzhong. Challenges and Perspective on Ring-Opening Polymerization-Induced Self-Assembly [J]. Acta Chimica Sinica, 2020, 78(8): 719-724.
[12]	Yin Cen, Wang Zikuan, Liu Dan, Peng Zhantao, Song Huanjun, Zhu Hao, Chen Qiwei, Wu Kai. Adsorption and Self-assembly of meso-tetra(p-methoxyphenyl)-porphyrinatocobalt(II) on Coinage Metal Surfaces [J]. Acta Chimica Sinica, 2020, 78(7): 695-702.
[13]	Liu Mingqian, Wan Xizi, Wang Shutao. Super Adhesive of Nanoparticle Solutions [J]. Acta Chimica Sinica, 2020, 78(6): 463-465.
[14]	Qie Shuyan, Hao Ying, Liu Zongjian, Wang Jin, Xi Jianing. Advances in Cyclodextrin Polymers and Their Applications in Biomedicine [J]. Acta Chimica Sinica, 2020, 78(3): 232-244.
[15]	Shen Yanglin, Jin Junling, Duan Guangxiong, Xie Yunpeng, Lu Xing. Formation of Spindle-Like Ag₅₈ Cluster Induced by Isomerization of [Ag₁₄] [J]. Acta Chimica Sinica, 2020, 78(11): 1255-1259.