Citation: A. Andriianova, A. Shigapova, Y. Biglova, R. Salikhov, I. Abdrakhmanov, A. Mustafin. Synthesis and Physico-chemical Properties of (Co)polymers of 2-[(2E)-1-methyl-2-buten-1-yl]aniline and Aniline[J]. Chinese Journal of Polymer Science, ;2019, 37(8): 774-782. doi: 10.1007/s10118-019-2261-9 shu

Synthesis and Physico-chemical Properties of (Co)polymers of 2-[(2E)-1-methyl-2-buten-1-yl]aniline and Aniline

a.
Ufa Institute of Chemistry, Russian Academy of Sciences, October Av, 71, Ufa, 450054, Russia
b.
Bashkir State University, Z. Validi St, 32, Ufa, 450076, Russia

Corresponding author: A. Andriianova, an.chem17@gmail.com
Received Date: 16 January 2019
Revised Date: 1 March 2019
Available Online: 8 May 2019

A new soluble polymer on 2-[(2E)-1-methyl-2-buten-1-yl]aniline and its copolymers with aniline basis have been synthesized in various molar ratios. For all samples, the electrical conductivity, morphology, solubility, electrochemical properties, as well as spectral and molecular mass characteristics have been studied, and a comparative analysis with polyaniline has been carried out. The substituent introduced into the aniline aromatic ring significantly improves the solubility in typical organic solvents of a high molecular weight product. The morphology of the test compounds depends on the co-monomer ratio. As the content of the substituted aniline in the initial mixture increases, the morphology of the polymer changes from the inherent polyaniline fibrous microstructure to the globular one with irregular substituted polyaniline shapes and sizes. Electrochemical study of the samples revealed that the higher the oxidation potential, the wider the band gap (ranging from 2.00 to 2.15). The electrical conductivity decreases in proportion to the increase in the substituted aniline concentration of the initial co-monomer mixture and amounts to 12.5–35.7 × 10⁶ nSm.
- Polyaniline,
- 2-[(2E)-1-methyl-2-buten-1-yl]aniline,
- Copolymers,
- Solubility,
- Electrochemical properties,
- Electrical conductivity
1. [1]
  Jarjes, Z.; Samian, M.; AbGhani, S. Conductive polymers: Their preparations and catalyses on NADH oxidation at carbon cloth electrodes. Arab. J. Chem. 2015, 5, 726-731. DOI: 10.1016/j.arabjc.2013.05.021. doi: 10.1016/j.arabjc.2013.05.021
2. [2]
  Long, Y.; Li, M.; Gu, C.; Wan, M.; Duvail, J.; Liu, Z.; Fan, Z. Recent advances in synthesis, physical properties and applications of conducting polymer nanotubes and nanofibers. Prog. Polym. Sci. 2011, 36, 1415-1442. DOI: 10.1016/j.progpolymsci.2011.04.001. doi: 10.1016/j.progpolymsci.2011.04.001
3. [3]
  Salikhov, R.; Biglova, Y.; Mustafin, A. New organic polymers for solar cells. In Emerging solar energy materials. ed. by Sadia Ameen. IntechOpen 2018, 83−104.
4. [4]
  Nicolas-Debarnot, D.; Poncin-Epaillard, F. Polyaniline as a new sensitive layer for gas sensors. Anal. Chim. Acta. 2003, 475, 1-15. doi: 10.1016/S0003-2670(02)01229-1
5. [5]
  Stejskal, J.; Sapurina, I.; Trchova, M. Polyaniline nanostructures and the role of aniline oligomers in their formation. Prog. Polym. Sci. 2010, 35, 1420-1481. DOI: 10.1016/j.progpolymsci.2010.07.006. doi: 10.1016/j.progpolymsci.2010.07.006
6. [6]
  Bhadra, S.; Khastgir, D.; Singha, N. K., Lee, J. H. Progress in preparation, processing and applications of polyaniline. Prog. Polym. Sci. 2009, 34, 783-810. DOI: 10.1016/j.progpolymsci.2009.04.003. doi: 10.1016/j.progpolymsci.2009.04.003
7. [7]
  Ćirić-Marjanović, G. Recent advances in polyaniline research: Polymerization mechanisms, structural aspects, properties and applications. Synth. Met. 2013, 177, 1-47. DOI: 10.1016/j.synthmet.2013.06.004. doi: 10.1016/j.synthmet.2013.06.004
8. [8]
  Vivekanandan, J.; Ponnusamy, V.; Mahudeswaran, A.; Vijayanand, P. Synthesis and characterization and conductivity study of polyaniline by chemical oxidative and electrochemical methods. Arch. Appl. Sci. Res, 2011, 3, 147-153.
9. [9]
  Verma, D.; Dutta, V., Role of novel microstructure of polyaniline-CSA thin film in ammonia sensing at room temperature. Sens. Actuat. B: Chem. 2008, 134, 373-376. DOI: 10.1016/j.snb.2008.05.009. doi: 10.1016/j.snb.2008.05.009
10. [10]
  Shakoor, A.; Rizvi, T.; Sulaiman, M.; Nasir, M.; Ishtiaq, M. Electronic properties of aniline doped with dodecylbenzenesulphonic acid (PANI-DBSA) and poly(methyl methacrylate) (PMMA) blends in the presence of hydroquinone. J. Mater. Sci.: Mater. Electron. 2010, 21, 603-607. DOI 10.1007/s10854-009-9964-6. doi: 10.1007/s10854-009-9964-6
11. [11]
  Im, S.; Han, M.; Cho, S.; Oh, S. Preparation and characterization of polyaniline nanoparticles synthesized from DBSA micellar solution. Synth. Met., 2002, 126, 53-60.. DOI: 10.1016/S0379-6779(01)00494-5. doi: 10.1016/S0379-6779(01)00494-5
12. [12]
  Liu, J.; Hu, X.; Wang, X.; Yao, J.; Sun, D.; Fan, Z.; Guo, M. Facile synthesis of hollow microspheres of polyaniline using poly(sodium 4-styrenesulfonic acid) as dopant. Polym. Int., 2014, 63, 722-726. DOI: 10.1002/pi.4578. doi: 10.1002/pi.4578
13. [13]
  Summers, G.; Waware, U.; Maduwa, M., Conducting polyaniline nanorods doped with aromatic carboxyl chain end functionalized polymers. Synth. Met. 2015, 209, 251-261. DOI: 10.1016/j.synthmet.2015.07.026. doi: 10.1016/j.synthmet.2015.07.026
14. [14]
  Kabomo, T.; Scurrell, M. The effects of ring substituents in aniline on the reactivity of PANI with hydrogen tetrachloroaurate and the dispersion of gold nanoparticles. Polym. Adv. Technol. 2016, 27, 759-764. DOI: 10.1002/pat.3709. doi: 10.1002/pat.3709
15. [15]
  Khamngoen, K.; Paradee, N.; Sirivat, A. Chemical oxidation polymerization and characterization of poly ortho-anisidine nanoparticles. J. Polym. Res. 2016, 23, 172. doi: 10.1007/s10965-016-1073-7
16. [16]
  Liu, Y.; Li, S.; Yao, P.; Zhang, Q. Synthesis of organic soluble poly(substituted-aniline) from 2-methyl-6-ethylaniline tar. Int. J. Mod. Phys. B, 2017, 31, 1744091. doi: 10.1142/S021797921744091X
17. [17]
  Barbero, C.; Salavagione, H.; Acevedo, D.; Grumelli, D.; Garay, F.; Planes, G.; Miras, M. Novel synthetic methods to produce functionalized conducting polymers I. Polyanilines. Electrochim. Acta 2004, 49, 3671-3686. DOI: 10.1016/j.electacta.2003.11.035. doi: 10.1016/j.electacta.2003.11.035
18. [18]
  Waware, U.; Hamouda, A. M. S.; Rashid, M.; Summers, G. , The spectral and morphological studies of the conductive polyaniline thin film derivatives by the in situ copolymerization. J. Mater. Sci-Mater. El. 2017, 28, 15178-15183. DOI 10.1007/s10854-017-7395-3. doi: 10.1007/s10854-017-7395-3
19. [19]
  Thota, A.; Arukula, R.; Narayan, R.; Rao, C.; Raju, K. V. S. N. Energy storage and surface protection properties of dianiline co-polymers. RSC Adv., 2015, 5, 106523-106535. doi: 10.1039/C5RA11731C
20. [20]
  Tran, H.; D'Arcy, J.; Wang, Y.; Beltramo, P.; Strong, V.; Kaner, R. The oxidation of aniline to produce " polyaniline”: a process yielding many different nanoscale structures. J. Mater. Chem. 2011, 21, 3534-3550. DOI:10.1039/C0JM02699A. doi: 10.1039/C0JM02699A
21. [21]
  Waware, U.; Summers, G.; Hamouda, A. M. S.; Rashid, M. Synthesis and characterization of polyaniline, poly(3-fluoroaniline), and poly (aniline-co-3-fluoroaniline) derivatives obtained by chemical oxidative polymerization methods. Polym. Plast. Technol. Eng. 2017, 57, 1-11.
22. [22]
  Movahedifar, F.; Modarresi‐Alam, A. The effect of initiators and oxidants on the morphology of poly[(±)‐2‐(sec‐butyl) aniline] a chiral bulky substituted polyaniline derivative. Polym. Adv. Technol. 2016, 27, 131-139. DOI: 10.1002/pat.3614. doi: 10.1002/pat.3614
23. [23]
  Teasdale, P.; Spinks, G.; Kane-Maguire, L.; Wallace, G. Conductive electroactive polymers: Intelligent polymer systems. in Conductive electroactive polymers: Intelligent polymer systems, CRC, New York, 2008.
24. [24]
  Ortega, E.; Armijo, F.; Jessop, I.; Del Valle, M. A.; Díaz, F. R. Chemical synthesis and characterization of polyaniline derivatives: substituent effect on solubility and conductivity. J. Chil. Chem. Soc. 2013, 58, 1959-1962. DOI: 10.4067/S0717-97072013000400010. doi: 10.4067/S0717-97072013000400010
25. [25]
  Biglova, Yu.; Salikhov, R.; Abdrakhmanov, I.; Salikhov, T.; Safargalin, I.; Mustafin, A. Preparation and investigation of soluble functionalized polyanilines. Phys. Solid State 2017, 59, 1228-1233. DOI: 10.1134/S106378341706004X. doi: 10.1134/S106378341706004X
26. [26]
  Salavagione, H. Preparation and characterization of " clickable” polyaniline derivatives on graphene modified electrodes. J. Electroanal. Chem. 2016, 765, 118-125. DOI: 10.1016/j.jelechem.2015.07.037. doi: 10.1016/j.jelechem.2015.07.037
27. [27]
  Abdrakhmanov, I.; Mustafin, A.; Sharafutdinov, V. Claisen rearrangement in the series of aromatic amines, Gilem, Ufa, 2014.
28. [28]
  Cope, A.; Hardy, E. The introduction of substituted vinyl groups. V. A rearrangement involving the migration of an allyl group in a three-carbon system. J. Am. Chem. Soc. 1940, 62, 441-444. DOI: 10.1021/ja01859a055. doi: 10.1021/ja01859a055
29. [29]
  Abdrakhmanov, I.; Sharafutdinov, V. M.; Tolstikov, G. A. Amino-Kleisen rearrangement as a method for the synthesis of C-cycloalkanilanilines. Bull. Russ. Acad. Sci.: Chem. 1982, 9, 2160.
30. [30]
  Gvozdenović, M.; Jugović, B.; Stevanović, J.; Grgur, B. Electrochemical synthesis of electroconducting polymers. Hem. Ind. 2014, 68, 673-684. DOI: 10.2298/HEMIND131122008G. doi: 10.2298/HEMIND131122008G
31. [31]
  Aprano, G.; Leclerc, M.; Zotti, G. Steric and electronic effects in methyl and methoxy substituted polyanilines. J. Electroanal. Chem. 1993, 351, 145-158. DOI: 10.1016/0379-6779(93)90279-6. doi: 10.1016/0379-6779(93)90279-6
32. [32]
  Aprano, G.; Leclerc, M.; Zotti, G.; Schiavon, G. Synthesis and characterization of polyaniline derivatives: poly(2-alkoxyanilines) and poly(2,5-dialkoxyanilines). Chem. Mater. 1995, 7, 33-42. DOI: 10.1021/cm00049a008. doi: 10.1021/cm00049a008
33. [33]
  Wei, Y.; Focke, W.; Wnek, G.; Ray, A.; MacDiarmid, A. Synthesis and electrochemistry of alkyl ring-substituted polyanilines. J. Phys. Chem. 1989, 93, 495-499. DOI: 10.1021/j100338a095. doi: 10.1021/j100338a095
34. [34]
  Aymen, M.; Sami, S.; Ahmed, S.; Fethi, G.; Abdellatif, B., Correlation between Raman spectroscopy and electrical conductivity of graphite/polyaniline composites reacted with hydrogen peroxide. J. Phys. D: Appl. Phys. 2013, 46, 335103. DOI: 10.1088/0022-3727/46/33/335103. doi: 10.1088/0022-3727/46/33/335103
35. [35]
  Barbero, C.; Miras, M.; Haas, O.; Kötz, R. Direct in situ evidence for proton/anion exchange in polyaniline films by means of probe beam deflection. J. Electrochem. Soc., 1991, 138, 669-672. DOI: 10.1149/1.2085655. doi: 10.1149/1.2085655
36. [36]
  Lindfors, T.; Ivaska, A. pH sensitivity of polyaniline and its substituted derivatives. J. Electroanal. Chem. 2002, 531, 43-52. DOI: 10.1016/S0022-0728(02)01005-7. doi: 10.1016/S0022-0728(02)01005-7
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