Citation: Mojtaba Amininasab Seyed, Rashidi Azad, Taghavi Mehdi, Shami Zahed. Preparation and Characterization of Novel Thermostable Polyamides Bearing Different Photoactive Pendent Architectures with Antibacterial Properties[J]. Chinese Journal of Polymer Science, ;2016, 34(6): 766-776. doi: 10.1007/s10118-016-1798-0 shu

Preparation and Characterization of Novel Thermostable Polyamides Bearing Different Photoactive Pendent Architectures with Antibacterial Properties

a.
Department of Chemistry, University of Kurdistan, Sanandaj 66177-15175, Iran
b.
Polymer Chemistry Research Laboratory, Faculty of Science, Shahid Chamran University of Ahvaz 61357-43337, Iran

Corresponding author: Mojtaba Amininasab Seyed, m.amininasab@uok.ac.ir
Received Date: 22 December 2015
Revised Date: 28 February 2016

Fund Project:

Three diamine monomers with different derivatives of imidazole heterocyclic ring, aryl ethers and electron withdrawing trifluoromethyl groups in the backbone were synthesized and used in polycodensation reaction with various aliphatic and aromatic dicarboxylic acids for preparation of a series of novel polyamides (PAs). The PAs were obtained in high yields and possessed inherent viscosities in the range of 0.26-0.75 dL/g. All of the polymers were amorphous in nature, showed outstanding solubility and could be easily dissolved in amide-type polar aprotic solvents. They showed good thermal stability with glass transition temperatures between 162-302 ℃. Thermogravimetric analysis showed that all polymers were stable, with 10% weight loss recorded above 421 ℃ in N₂ atmospheres. All the PAs presented fluorescence upon irradiation with ultraviolet light and thus showed promise for applications in electroluminescent devices. The monomers and PAs were also screened for antibacterial activity against Gram positive and Gram negative bacteria.
- Photoactive polyamides,
- Anthracene,
- Fluorene,
- Carbazole,
- Antibacterial activity
1. [1]
  García, J.M., García, F.C., Serna, F. and de la Peña, J.L., Prog. Polym. Sci., 2010, 5: 623
2. [2]
  Hearle, J.W., "High-performance fibres." Cambridge, England: Woodhead Publishing Ltd, 2001
3. [3]
  Carja, I.D., Hamciuc, C., Hamciuc, E., Bubulac, T.V. and Lisa, G., Macromol. Res., 2012, 20: 1011
4. [4]
  Taghavi, M., Ghaemy, M., Amini Nasab, S.M. and Hassanzadeh, M., Polymer, 2013, 54: 3828
5. [5]
  Liaw, D.J., Hsu, P.N., Chen, W.H. and Lin, S.L., Macromolecules, 2002, 35: 4669
6. [6]
  Ghaemy, M. and Khajeh, S., Chinese J. Polym. Sci., 2012, 30(1): 82
7. [7]
  7 haemy, M. and Amini Nasab, S.M., Polym. Adv. Technol., 2011, 22: 2311
8. [8]
  Mighani, H. and Ghaemy, M., Chinese J. Polym. Sci., 2010, 28(2): 147
9. [9]
  Wang, W.Z. and Zhang, Y.H., Chinese J. Polym. Sci., 2010, 28(4): 467
10. [10]
  Ghaemy, M. and Amini Nasab, S.M., React. Funct. Polym., 2010, 70: 306
11. [11]
  Sava, I. and Bruma, M., Macromol. Symp., 2006, 239: 36
12. [12]
  Ion, S. and Maria, B., High. Perform. Polym., 2004, 16: 435
13. [13]
  Zhang, G., Bai, D.T., Li, D.S., Long, S.R., Wang, X.J. and Yang, J., Polym. Int., 2013, 62: 1358
14. [14]
  Li, Z.M., Zhang, G., Li, D.S. and Yang, J., Chinese J. Polym. Sci., 2014, 32(3): 292
15. [15]
  Liaw, D.J. and Liaw, B.Y., Polym. J., 2001, 33: 204
16. [16]
  Liou, J.S., Yen, H.J., Su, Y.T. and Lin, H.Y., J. Polym. Sci., Part A: Polym. Chem. Ed., 2007, 45: 4352
17. [17]
  Ghaemy, M., Nasr, F.H., Alizadeh, R. and Taghavi, M., Macromol. Res., 2012, 20: 614
18. [18]
  Ghaemy, M., Aghakhani, B., Taghavi, M., Amini Nasab, S.M. and Mohseni, M., React. Funct. Polym., 2013, 73: 555
19. [19]
  Ghaemy, M., Hassanzadeh, M., Amini Nasab, S.M. and Taghavi, M., Polym. J., 2013, 45: 622
20. [20]
  Wu, S.C. and Shu, C.F., J. Polym. Sci., Part A: Polym. Chem., 2003, 41: 1160
21. [21]
  Mitschke, U. and Bauerle, P.J., Mater. Chem., 2000, 10: 1471
22. [22]
  Gu, J., Kawabe, M., Masuda, K. and Namba, S., J. Appl. Phys., 1977, 48: 2493
23. [23]
  Garay, R.O., Naarmann, H. and Mullen, K., Macromolecules, 1994, 27: 1922
24. [24]
  Kan, Y., Wang, L., Gao, Y., Duan, L., Wu, G. and Qiu, Y., Synth. Met., 2004, 141: 245
25. [25]
  Sui, J. and Tang, C.W., Appl. Phys. Lett., 2002, 80: 3201
26. [26]
  Pandey, J., Tiwari, V.K., Verma, S.S., Chaturvedi, V., Bhatnagar, S., Sinha, S., Gaikwad, A.N. and Tripathi, R.P., Eur. J. Med. Chem., 2009, 44: 3350
27. [27]
  Zampieri, D., Mamolo, M.G., Laurini, E., Scialino, G., Banfi, E. and Vio, L., Bioorg. Med. Chem. Lett., 2008, 16: 4516
28. [28]
  Colonna, M., Berti, Binassi, C.E., Fiorini, M., Sullalti, S., Acquasanta, F., Vannini, M., Gioia, D.D., Aloisio, I., Karanam, S. and Brunelle, D.J., React. Funct. Polym., 2012, 72: 133
29. [29]
  Chang, H.I., Yang, M.S. and Liang, M., React. Funct. Polym., 2010, 70: 944
30. [30]
  Anderson, E.B. and Long, T.E., Polymer, 2010, 51: 2447
31. [31]
  Yamazaki, N., Matsumoto, M. and Higashi, F., J. Polym. Sci. A: Polym. Chem., 1975, 13: 1373
32. [32]
  Ge, Z., Yang, S., Tao, Z., Liu, J. and Fan, L., Polymer, 2004, 45: 3627
33. [33]
  Sheng, S.R., Pei, X.L., Huang, Z.Z., Liu, X.L. and Song, C.S., Eur. Polym. J., 2009, 45: 230
34. [34]
  Feng, K., Hsub, F.L., Van DerVeer, D., Bota, K. and Xiu, R., Photochem. Photobiol. A Chem., 2004, 165: 223
35. [35]
  Liou, G.S. and Chang, C.W., Macromolecules, 2008, 41: 1667
36. [36]
  Van Krevelen, D.W. and Hoftyzer, P.J., "Properties of polymers", 4rd ed., Amsterdam, Elsevier Scientic Publishing, 2008
37. [37]
  Zhang, F.F., Gan, L.L. and Zhou, C.H., Bioorg. Med. Chem. Lett., 2010, 20: 1881
1. [1]
  Xiaoxue Li , Hongwei Zhou , Rongrong Qian , Xu Zhang , Lei Yu . A concise synthesis of Se/Fe materials for catalytic oxidation reactions of anthracene and polyene. Chinese Chemical Letters, 2025, 36(3): 110036-. doi: 10.1016/j.cclet.2024.110036
2. [2]
  Xingyu Chen , Sihui Zhuang , Weiyao Yan , Zhengli Zeng , Jianguo Feng , Hongen Cao , Lei Yu . Synthesis, antibacterial evaluation, and safety assessment of Se@PLA as a potent bactericide against Xanthomonas oryzae pv. oryzae. Chinese Chemical Letters, 2024, 35(10): 109635-. doi: 10.1016/j.cclet.2024.109635
3. [3]
  Jiaxi Wang , Zhiwei Gao , Hao Liang , Qianyue Liu , Weiqian Jin , Huyang Gao , Bailei Wang , Ruikai Zhu , Jiahao Huang , Xiaowen Li , Xingmou Wu , Weijiu Mo , Yinhan Liao , Ming Gao , Xiaojie Li , Cuiping Li . NIR stimulated epigallocatechin gallate loaded polydopamine with enhanced antibacterial and ROS scavenging abilities for improved infectious wound healing. Chinese Chemical Letters, 2025, 36(7): 110569-. doi: 10.1016/j.cclet.2024.110569
4. [4]
  Yan Zhu , Jia Liu , Meiheng Lv , Tingting Wang , Dongxiang Zhang , Rong Shang , Xin-Dong Jiang , Jianjun Du , Guiling Wang . Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation. Chinese Chemical Letters, 2024, 35(10): 109446-. doi: 10.1016/j.cclet.2023.109446
5. [5]
  Yanye Fan , Jingjing Chen , Bichun Chen , Jinyu Bai , Bowen Yang , Feng Liang , Lijing Fang . Design, synthesis and biological evaluation of Leu₁₀-teixobactin analogues. Chinese Chemical Letters, 2025, 36(4): 110075-. doi: 10.1016/j.cclet.2024.110075
6. [6]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
7. [7]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
8. [8]
  Jiming XI , Yukang TENG , Rui ZHANG , Zhenzhong LU . Fluorescent coordination polymers based on anthracene-and pyrene-derivative ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 847-854. doi: 10.11862/CJIC.20240367
9. [9]
  Liangji Chen , Zhen Yuan , Fudong Feng , Xin Zhou , Zhile Xiong , Wuji Wei , Hao Zhang , Banglin Chen , Shengchang Xiang , Zhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344
10. [10]
  Zhaoyue Lü , Tiantian Chai , Yichao Jin , Xiao Wang , Ye Zou , Lijiang Zhang , Jiankang Feng , Mengtong Zhang , Shuo Wang , Chichong Lu , Guofan Jin . Asymmetrical carbazole-benzonitrile-based TADF emitters designed by alternate donor-acceptor strategy. Chinese Chemical Letters, 2025, 36(6): 110817-. doi: 10.1016/j.cclet.2025.110817
11. [11]
  Dan Luo , Jinya Tian , Jianqiao Zhou , Xiaodong Chi . Anthracene-bridged "Texas-sized" box for the simultaneous detection and uptake of tryptophan. Chinese Chemical Letters, 2024, 35(9): 109444-. doi: 10.1016/j.cclet.2023.109444
12. [12]
  Yan-Kai Zhang , Yong-Zheng Zhang , Chun-Xiao Jia , Fang Wang , Xiuling Zhang , Yuhang Wu , Zhongmin Liu , Hui Hu , Da-Shuai Zhang , Longlong Geng , Jing Xu , Hongliang Huang . A stable Zn-MOF with anthracene-based linker for Cr(VI) photocatalytic reduction under sunlight irradiation. Chinese Chemical Letters, 2024, 35(12): 109756-. doi: 10.1016/j.cclet.2024.109756
13. [13]
  Ying-Mei Zhong , Zi-Jun Xia , Yu-Hang Hu , Li-Peng Zhou , Li-Xuan Cai , Qing-Fu Sun . Effective separation of phenanthrene from isomeric anthracene using a water-soluble macrocycle-based cage. Chinese Chemical Letters, 2025, 36(4): 110164-. doi: 10.1016/j.cclet.2024.110164
14. [14]
  Junjie Wang , Yan Wang , Zhengdong Li , Changqiang Xie , Musammir Khan , Xingzhou Peng , Fabiao Yu . Triphenylamine-AIEgens photoactive materials for cancer theranostics. Chinese Chemical Letters, 2024, 35(6): 108934-. doi: 10.1016/j.cclet.2023.108934
15. [15]
  Lihua Ma , Song Guo , Zhi-Ming Zhang , Jin-Zhong Wang , Tong-Bu Lu , Xian-Shun Zeng . Sensitizing photoactive metal–organic frameworks via chromophore for significantly boosting photosynthesis. Chinese Chemical Letters, 2024, 35(5): 108661-. doi: 10.1016/j.cclet.2023.108661
16. [16]
  Jinjie Lu , Qikai Liu , Yuting Zhang , Yi Zhou , Yanbo Zhou . Antibacterial performance of cationic quaternary phosphonium-modified chitosan polymer in water. Chinese Chemical Letters, 2024, 35(9): 109406-. doi: 10.1016/j.cclet.2023.109406
17. [17]
  Wei Su , Xiaoyan Luo , Peiyuan Li , Ying Zhang , Chenxiang Lin , Kang Wang , Jianzhuang Jiang . Phthalocyanine self-assembled nanoparticles for type Ⅰ photodynamic antibacterial therapy. Chinese Chemical Letters, 2024, 35(12): 109522-. doi: 10.1016/j.cclet.2024.109522
18. [18]
  Qihang Wu , Hui Wen , Wenhai Lin , Tingting Sun , Zhigang Xie . Alkyl chain engineering of boron dipyrromethenes for efficient photodynamic antibacterial treatment. Chinese Chemical Letters, 2024, 35(12): 109692-. doi: 10.1016/j.cclet.2024.109692
19. [19]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
20. [20]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(926)
HTML views(6)

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