New Polymer Syntheses Part: 55#. Novel Conducting Arylidene Polymers and Copolymers Based on Methyl-Cyclohexanone Moiety
DOI:
https://doi.org/10.6000/1929-5995.2014.03.02.4Keywords:
Synthesis, Characterization, Polycondensation, Conducting Polymers, Conducting Copolymers.Abstract
A new interesting class of conducting polymers based on methyl-cyclohexanone in the polymer main chain has been synthesized by solution polycondensation of terephthalaldehyde with methyl-cyclohexanone. Copolymers containing different cycloalkanone moieties were also synthesized using solution polycondensation technique. The model compound I was synthesized by the interaction of methyl-cyclohexanone monomer with benzaldehyde, and its structure was confirmed by elemental and spectral analyses. The resulting new polymers and copolymers were characterized by elemental and spectral analyses, beside solubility and viscometry measurements. The thermal properties of those polymer and copolymers were evaluated by TGA, DrTGA and DTA measurements and correlated to their structural units. PDT as well as T10 was in the range from 205 to 370 ºC. In addition, T10 thermal stability for all the polymers was in the order: VI> II > III > IV > V. X– ray analysis showed that it has some degree of crystallinity in the region 2q = 5 – 60 degree.The UV– visible spectra of some selected polymers were measured in DMSO solution and showed absorption bands in the range 265-397 nm, due to n – p* and p – p* transition. The morphological properties of copolymer IV as selected examples were tested by SEM. The electrical conductivities of the synthesized polymers and copolymers enhanced to become in the range of 10-9-10-8 S cm-1 by doping with iodine.
References
Berlin A. Heterocycle-based electroconductive polymers. in: Wise DL, Wnek GE, Trantolo DJ, Cooper TM, Gresser JD. Eds. Electrical and Optical Polymer Systems: Fundamentals, Methods, and Applications. Marcel Dekker: New York 1998; pp. 47-95.
Hotta S. in: Nalwa HS, Ed. Handbook of Organic Conductive Molecules and Polymers: Conductive Polymers: Synthesis and Electrical Properties. Vol. 2 Wiley: Chichester 1997; pp. 310-387.
Leclerc M, Faid K. Electrical and optical properties of Processable Polythiophene Derivatives: Structure-Property relationships. Adv Mater 1997; 9: 1087-94. http://dx.doi.org/10.1002/adma.19970091404 DOI: https://doi.org/10.1002/adma.19970091404
Hwang J, Tanner DB, Schwendeman I, Reynolds JR. Optical properties of nondegenerate ground-state polymers: Three dioxythiophene-based conjugated polymers. Phys Rev 2003; B67: 115205 (1-10). DOI: https://doi.org/10.1103/PhysRevB.67.115205
Hoffmann KJ, Samuelsen EJ, Carlsen PHJ. Broken π-conjugated thiophene systems: 1. Synthesis and polymerization of 2,2′-di(alkylthienyl) methanes. Synth Met 2000; 113: 161-66. http://dx.doi.org/10.1016/S0379-6779(00)00209-5 DOI: https://doi.org/10.1016/S0379-6779(00)00209-5
Chen W-C, Jenekhe SA. Small-Bandgap Conducting Polymers Based on Conjugated Poly(heteroarylene methines). 1. Precursor Poly(heteroarylene methylenes). Macromol 1995; 28: 454-64. http://dx.doi.org/10.1021/ma00106a008 DOI: https://doi.org/10.1021/ma00106a008
Chen W-C, Jenekhe SA. Small-Bandgap Conducting Polymers Based on Conjugated Poly(heteroarylene methines). 2. Synthesis, Structure, and Properties. Macromol 1995; 28: 465-80. http://dx.doi.org/10.1021/ma00106a009 DOI: https://doi.org/10.1021/ma00106a009
Miller LL, Mann KR. π-Dimers and π-Stacks in Solution and in Conducting Polymers. Acc Chem Res 1996; 29: 417-23. http://dx.doi.org/10.1021/ar9600446 DOI: https://doi.org/10.1021/ar9600446
Borden DG, Unruh CC, Merrill SH. Eastman Kodak Company. United States Patent. 3 453 237, 1969 July.
Borden D, Unruh CC, Merrill SH. Eastman Kodak Company. United States Patent. 3 647 444, 1972 March.
Aly KI, Hammam AS, Radwan SM, Abdel-Rahman MA. New Unsaturated Copolyesters based on Diarylidenecyclo-pentanone. Optimum conditions of Synthesis, Characteri-zation and Morphology. Int J Bas Appl Sci 2011; 11: 15-36.
Aly KI, Abdel-Rahman MA, Hussein MA. New Polymer Syntheses Part 53. Novel Polyamides of Diarylidenecyclo-alkanone Containing Azo Groups in the Polymer Backbone: Synthesis and Characterization. Int J Polym Mat 2010; 59: 553-69. http://dx.doi.org/10.1080/00914031003760667 DOI: https://doi.org/10.1080/00914031003760667
Aly KI, Hussein MA. New polymer syntheses, part 45: Corrosion inhibition behavior of novel polyurea derivatives based on diarylidenecyclo-alkanone moieties in the polymers backbone. J Polym Res 2010; 17: 607-20. http://dx.doi.org/10.1007/s10965-009-9349-9 DOI: https://doi.org/10.1007/s10965-009-9349-9
Aly KI, Wahdan MH, Hussein MA. New Polymer Syntheses, Part 43: Novel Polyamides-Based Diarylidenecyclo-pentanone: Synthesis, Characterization, and Corrosion Inhibition Behavior. J Appl Polym Sci 2009; 112: 513-23. http://dx.doi.org/10.1002/app.29344 DOI: https://doi.org/10.1002/app.29344
Al-Muaikel NS, Aly KI, Hussein MA. Synthesis, Characterization and Antimicrobial Properties of New Poly(ether-ketone)s and Copoly(ether-ketone)s Containing Diarylidenecycloalkanone Moieties in the Main Chain. J Appl Polym Sci 2008; 108: 3138-47. http://dx.doi.org/10.1002/app.27963 DOI: https://doi.org/10.1002/app.27963
Aly KI, Abdel Monem MI. New Polymer Synthesis. XXX. Synthesis and Thermal Behavior of New Organometallic Polyketones and Copolyketones Based on Diferrocenyli-denecycloheptanone. J Appl Polym Sci 2005; 98: 2394-401. http://dx.doi.org/10.1002/app.22420 DOI: https://doi.org/10.1002/app.22420
Aly KI, Abbady MA, Mahgoub SA, Hussein MA. New polymer syntheses. Part 14. Synthesis and properties of new polyketoamine polymers containing cycloalkanone moieties in the main chain. J Polym Int 2002; 51: 125-33. http://dx.doi.org/10.1002/pi.798 DOI: https://doi.org/10.1002/pi.798
Khalaf AA, Aly KI, Mohammed IA. New polymer synthesis XIII. Synthesis and characterization of novel polyketones via Friedel-Crafts reaction and based on diarylidene derivatives. J Macromol Sci - Pure Appl Chem 2002; A39: 333-50. DOI: https://doi.org/10.1081/MA-120003283
Aly KI. New polymer syntheses. V. Synthesis, characterization, and morphology of new conjugated polymers, copolymers, and terpolymers containing piperidone moiety in main chain. J Appl Polym Sci 1999; 74: 2369-77. http://dx.doi.org/10.1002/(SICI)1097-4628(19991205)74:10<2369::AID-APP4>3.0.CO;2-T DOI: https://doi.org/10.1002/(SICI)1097-4628(19991205)74:10<2369::AID-APP4>3.0.CO;2-T
Aly KI, Khalaf AA. New polymer syntheses. IX. Synthesis and properties of new conducting polyazomethine polymers containing main chain cycloalkanone and pyridine moieties. J Appl Polym Sci 2000; 77: 1218-29. http://dx.doi.org/10.1002/1097-4628(20000808)77:6<1218::AID-APP6>3.0.CO;2-G DOI: https://doi.org/10.1002/1097-4628(20000808)77:6<1218::AID-APP6>3.0.CO;2-G
Aly KI. New polymer syntheses part: 54 novel conducting polymers and copolymers based on 4-Teriary butyl-cyclohexanone moiety in the main chain. J Appl Polym Sci 2012; 123: 3390-401. http://dx.doi.org/10.1002/app.34421 DOI: https://doi.org/10.1002/app.34421
Abo Zaid EF. Study of Electrical and Thermophysical Properties of Basalt and Granite Rock Samples (Msc) thesis. Assiut University, Faculty of Science, Assiut, Egypt 2001.
Silverstein RM, Bassler GC, Morrill TC. Spectrometric Identification of Organic Compounds. New York: Wiley 1974.
Skoog DA, West DM. Principles of Instrumental Analysis. New York: Holt Rinhart Winston 1971.
Li Z, Fu W, Yu M, Zhao X, Chen Y. The synthesis and properties of phenolic Schiff bases based on 1,8-naphthyridine. Dyes Pigm 2007; 75: 516-20. http://dx.doi.org/10.1016/j.dyepig.2006.06.030 DOI: https://doi.org/10.1016/j.dyepig.2006.06.030
Kumar V, Jaggi M, Singh AT, Madaan A, Sanna V, Singh P, Sharma PK, Irchhaiya R, Burman AC. 1,8-Naphthyridine-3-carboxamide derivatives with anticancer and anti-inflammatory activity. Eur J Med Chem 2009; 44: 3356-62. http://dx.doi.org/10.1016/j.ejmech.2009.03.015 DOI: https://doi.org/10.1016/j.ejmech.2009.03.015
Di-Braccio M, Grossi G, Roma G, Piras D, Mattioli F, Gosmar M. 1,8-Naphthyridines VI. Synthesis and anti-inflammatory activity of 5-(alkylamino)-N,N-diethyl[1,2,4]triazolo[4,3-a][1,8] naphthyridine-6-carboxamid-es with a new substitution pattern on the triazole ring. Eur J Med Chem 2008; 43: 584-94. http://dx.doi.org/10.1016/j.ejmech.2007.04.016 DOI: https://doi.org/10.1016/j.ejmech.2007.04.016
Tager A. Physical Chemistry of Polymers. Mir: Moscow 1972.
Mandelkern L. Crystallization of Polymers. McGraw-Hill: New York 1964. DOI: https://doi.org/10.1063/1.3051751
Sheng-Huei H, Guey-Sheng L. A New Class of Aromatic Poly(1,3,4-oxadiazole)s and Poly(amide-1,3,4-oxadiazole)s Containing (Naph-thalenedioxy)diphenylene Groups. Polym J 2002; 34: 917-24. http://dx.doi.org/10.1295/polymj.34.917 DOI: https://doi.org/10.1295/polymj.34.917
Hussein MA, Asiri AM, Aly KI. New Polyamides and Polyoxazoles Based on Diphenyl Ether Segments in the Polymers' Backbone. Int J Polym Mater 2012; 6: 154-75. http://dx.doi.org/10.1080/00914037.2011.593059 DOI: https://doi.org/10.1080/00914037.2011.593059
Hussein MA, Abdel Rahman MA, Aly KI. New Polymer Syntheses Part 56: Novel Friedel-Crafts Polyketones Containing Naphthalene Moiety: Synthesis, Characterization and Antimicrobial Activity. J Macromol Sci - Pure Appl Chem 2013; A50: 99-109. DOI: https://doi.org/10.1080/10601325.2013.736268
Ander ME. Geophysical study of the crust and upper mantle beneath the central Rio Grande rift and adjacent Great Plains and Colorado Plateau. Tech. Rept. LA – 8676-T, Los Alamos Natl. Lab., Los Alamos, N. Mex., Dec. 218. 1980. DOI: https://doi.org/10.2172/6577821
Kaufman A, Keller GR. The Magnetotelluric Sounding Method. Elsevier: New York 1981; p. 595.
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