Synthesis and Physico-chemical Properties of (Co)polymers of 2-[(2<italic style="font-style: italic">E</italic>)-1-methyl-2-buten-1-yl]aniline and Aniline

A. Andriianova; A. Shigapova; Y. Biglova; R. Salikhov; I. Abdrakhmanov; A. Mustafin

doi:10.1007/s10118-019-2261-9

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

ARTICLE | Updated：2021-02-18

- Synthesis and Physico-chemical Properties of (Co)polymers of 2-[(2E)-1-methyl-2-buten-1-yl]aniline and Aniline
- Synthesis and Physico-chemical Properties of (Co)polymers of 2-[(2E)-1-methyl-2-buten-1-yl]aniline and Aniline
- Chinese Journal of Polymer Science 2019年37卷第8期页码：774-782
- Affiliations：
  
  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
- Author bio：
  
  an.chem17@gmail.com
- Funds：
  
  This work was carried out within the framework of the state task program (No. AAAA-A19-119020890014-7). Electron microscopic studies were performed on the basis of the Center for Collective Use of Scientific Equipment of the Institute of Metal Superplasticity Problems, RAS "Structural and Physico-Mechanical Material Studies".
- DOI：10.1007/s10118-019-2261-9
  中图分类号：
- 收稿：2019-01-16，
  
  修回：2019-3-1，
  
  录用：2019-3-21，
  
  网络首发：2019-05-08，
  
  纸质出版：2019-08
- Accepted：
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Citation: Andriianova, A.; Shigapova, A.; Biglova, Y.; Salikhov, R.; Abdrakhmanov, I.; Mustafin, A. Synthesis and physico-chemical properties of (co)polymers of 2-[(2, E,)-1-methyl-2-buten-1-yl]aniline and aniline. Chinese J. Polym. Sci. 2019, 37, 774–782

A. Andriianova, A. Shigapova, Y. Biglova, et al. 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.
Citation: Andriianova, A.; Shigapova, A.; Biglova, Y.; Salikhov, R.; Abdrakhmanov, I.; Mustafin, A. Synthesis and physico-chemical properties of (co)polymers of 2-[(2, E,)-1-methyl-2-buten-1-yl]aniline and aniline. Chinese J. Polym. Sci. 2019, 37, 774–782 DOI： 10.1007/s10118-019-2261-9.

A. Andriianova, A. Shigapova, Y. Biglova, et al. 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. DOI：

摘要

Abstract

A new soluble polymer on 2-[(2

)-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 × 10

nSm.

关键词

Keywords

references

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 http://doi.org/10.1016/j.arabjc.2013.05.021 .

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 http://doi.org/10.1016/j.progpolymsci.2011.04.001 .

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.

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 http://doi.org/10.1016/S0003-2670(02)01229-1 .

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 http://doi.org/10.1016/j.progpolymsci.2010.07.006 .

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 http://doi.org/10.1016/j.progpolymsci.2009.04.003 .

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 http://doi.org/10.1016/j.synthmet.2013.06.004 .

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 . .

Verma, D . 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 http://doi.org/10.1016/j.snb.2008.05.009 .

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 http://doi.org/10.1007/s10854-009-9964-6 .

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 http://doi.org/10.1016/S0379-6779(01)00494-5 .

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 http://doi.org/10.1002/pi.4578 .

Summers, G . 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 http://doi.org/10.1016/j.synthmet.2015.07.026 .

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 http://doi.org/10.1002/pat.3709 .

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 http://doi.org/10.1007/s10965-016-1073-7 .

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 http://doi.org/10.1142/S021797921744091X .

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 http://doi.org/10.1016/j.electacta.2003.11.035 .

Waware, U . 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 http://doi.org/10.1007/s10854-017-7395-3 .

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 http://doi.org/10.1039/C5RA11731C .

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 http://doi.org/10.1039/C0JM02699A .

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 . .

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 http://doi.org/10.1002/pat.3614 .

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 .

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 http://doi.org/10.4067/S0717-97072013000400010 .

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 http://doi.org/10.1134/S106378341706004X .

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 http://doi.org/10.1016/j.jelechem.2015.07.037 .

Abdrakhmanov, I.; Mustafin, A.; Sharafutdinov, V. Claisen rearrangement in the series of aromatic amines , Gilem, Ufa, 2014 .

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 http://doi.org/10.1021/ja01859a055 .

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 .

Gvozdenović, M.; Jugović, B.; Stevanović, J.; Grgur, B . Electrochemical synthesis of electroconducting polymers . Hem. Ind. , 2014 . 68 673 - 684 . DOI: 10.2298/HEMIND131122008G http://doi.org/10.2298/HEMIND131122008G .

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 http://doi.org/10.1016/0379-6779(93)90279-6 .

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 http://doi.org/10.1021/cm00049a008 .

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 http://doi.org/10.1021/j100338a095 .

Aymen, M . 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 http://doi.org/10.1088/0022-3727/46/33/335103 .

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 http://doi.org/10.1149/1.2085655 .

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 http://doi.org/10.1016/S0022-0728(02)01005-7 .

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DOI：10.1007/s10118-019-2261-9

摘要

Abstract

关键词

Keywords

references