Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Synthesis, Characterization and Antimicrobial Activity Evaluation of the Polybenzimidazole Derivatives with Different Dicarboxylic Acid Moieties

Author(s): Bilge Eren*, Fadime Özdemir Koçak and Gülcan Erdoğan

Volume 17, Issue 7, 2020

Page: [539 - 547] Pages: 9

DOI: 10.2174/1570178617666191114105457

Price: $65

Abstract

A series of polybenzimidazole was synthesized by the solution polycondensation reaction of 3,3´-diaminobenzidine (DAB) with dicarboxylic acid derivatives. The synthesized polybenzimidazoles were characterized by using IR, 1H-NMR, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). TGA and DSC studies showed that the polybenzimidazoles have good thermal stability and are generally amorphous in nature. Glass transition temperature (Tg) values were found to be in the range of 300-410°C. This is the first detailed study to investigate the antimicrobial activities of the polybenzimidazoles. The synthesized polybenzimidazoles have high antimicrobial activity compared to benzimidazole molecules. It was also found that they are more effective against bacterial species than fungal species. The polymers 2, 5, 6, 7, having -1,3-phenyl, vinyl, -1-OH-3,5-phenyl and 4,4´- oxybisphenyl rings, showed remarkable activity against tested bacterial species (MIC = 32-500 μg/mL). Among these polymers, the polymers 6 and 7 having additional electronegative moiety have the highest activity against tested bacterial species.

Keywords: Benzimidazole, synthesis, polymer, polybenzimidazole, PBI, antimicrobial activity.

Graphical Abstract

[1]
Munoz-Bonilla, A.; Fernández-García, A. Prog. Polym. Sci., 2012, 37, 281-339.
[http://dx.doi.org/10.1016/j.progpolymsci.2011.08.005]
[2]
Tahlan, S.; Kumar, S.; Narasimhan, B. BMC Chem., 2019, 13(1), 18-44.
[http://dx.doi.org/10.1186/s13065-019-0521-y] [PMID: 31384767]
[3]
Mallakpour, S.; Abdolmaleki, A.; Borandeh, S.; Sabzalian, M.R. J. Polym. Res., 2015, 22, 129-137.
[http://dx.doi.org/10.1007/s10965-015-0743-1]
[4]
Usta, A.; Yılmaz, F.; Kapucu, G.; Baltas, N.; Mentese, E. Lett. Org. Chem., 2015, 12, 227-232.
[http://dx.doi.org/10.2174/1570178612666150203233804]
[5]
Kumbharkar, S.C.; Islam, M.N.; Potrekar, R.A.; Kharul, U.K. Polymer (Guildf.), 2009, 50, 1403-1413.
[http://dx.doi.org/10.1016/j.polymer.2009.01.043]
[6]
Eren, E.; Sarihan, A.; Eren, B.; Gumus, H.; Ozdemir Kocak, F. J. Membr. Sci., 2015, 475, 1-8.
[http://dx.doi.org/10.1016/j.memsci.2014.10.010]
[7]
Eren, B.; Yılmaz, O.; Cetin, G.; Darcan, C. Lett. Drug Des. Discov., 2018, 15, 621-633.
[http://dx.doi.org/10.2174/1570180814666170823162419]
[8]
Eren, B.; Aydin, R.; Eren, E. J. Therm. Anal. Calorim., 2014, 115, 1525-1531.
[http://dx.doi.org/10.1007/s10973-013-3470-z]
[9]
Iwakura, Y.; Uno, K.; Imal, Y. J. Polym. Sci. A, 1964, 2, 2605-2615.
[http://dx.doi.org/10.1002/pol.1964.100020611]
[10]
Preston, P.N. Benzimidazoles and Cogeneric Tricyclic Compounds. The Chemistry of Heterocyclic Compounds; Weisberger, A; Taylor, E.C., Ed.; John Wiley & Sons: New York, 2009, Vol. 40, pp. 38-154.
[11]
Sundaraganesan, N.; Ilakiamani, S.; Subramani, P.; Dominic Joshua, B. Spectrochim. Acta A., 2007, 67, 628-635.
[http://dx.doi.org/10.1016/j.saa.2006.08.020]
[12]
Ozdemir, N.; Eren, B. Int. J. Quantum Chem., 2011, 111, 3112-3124.
[13]
Unal, A.; Eren, B. Spectrochim. Acta A., 2013, 114, 129-136.
[http://dx.doi.org/10.1016/j.saa.2013.05.045]
[14]
Sridharan, V.; Saravanan, S.; Muthusubramanian, S.; Sivasubramanian, S. Magn. Reson. Chem., 2005, 43(7), 551-556.
[http://dx.doi.org/10.1002/mrc.1588] [PMID: 15861488]
[15]
Kojima, T. J. Polym. Sci. B, 1980, 18, 1791-1800.
[16]
Kim, S.K.; Kim, T.H.; Ko, T.; Lee, J.C. J. Membr. Sci., 2011, 373, 80-88.
[http://dx.doi.org/10.1016/j.memsci.2011.02.039]
[17]
Vogel, H.; Marvel, C.S. J. Polym. Sci. A, 1961, 50, 511-539.
[18]
Jing, J.A.; Zhang, A.; Wu, Z. Thermal Analysis of Polymer Fibers.Handbook of Thermal Analysis and Calorimetry; Z.D; Cheng, S., Ed.; Elsevier Science B. V: Amsterdam, 2002, Vol. 3, pp. 474-476.
[19]
Samms, S.R.; Wasmus, S.; Savinell, R.F. J. Electrochem. Soc., 1996, 143, 1225-1232.
[http://dx.doi.org/10.1149/1.1836621]
[20]
Nores-Pondal, F.J.; Buera, M.P.; Corti, H.R. J. Power Sources, 2010, 195, 6389-6397.
[http://dx.doi.org/10.1016/j.jpowsour.2010.04.009]
[21]
Ma, T.; Li, Y.F.; Zhang, S.J.; Yang, F.C.; Gong, C.L.; Zhao, J.J. Chin. Chem. Lett., 2010, 21, 1976-1978.
[22]
Liu, C.; Li, X.; Xu, J.; Jian, X. Eur. Polym. J., 2011, 47, 1852-1860.
[http://dx.doi.org/10.1016/j.eurpolymj.2011.06.018]
[23]
Maity, S.; Sannigrahi, A.; Ghosh, S.; Jana, T. Eur. Polym. J., 2013, 49, 2280-2292.
[http://dx.doi.org/10.1016/j.eurpolymj.2013.05.011]
[24]
Ansari, K.F.; Lal, C. Eur. J. Med. Chem., 2009, 44(10), 4028-4033.
[http://dx.doi.org/10.1016/j.ejmech.2009.04.037] [PMID: 19482384]
[25]
Küçükbay, H.; Durmaz, R.; Orhan, E.; Günal, S. Farmaco, 2003, 58(6), 431-437.
[http://dx.doi.org/10.1016/S0014-827X(03)00068-5] [PMID: 12767382]
[26]
Sharma, M.C. J. Saudi Chem. Soc., 2012, 19, 265-273.
[27]
Sharma, D.; Narasimhan, B.; Kumar, P.; Jalbout, A. Eur. J. Med. Chem., 2009, 44(3), 1119-1127.
[http://dx.doi.org/10.1016/j.ejmech.2008.06.009] [PMID: 18657885]
[28]
Abdel Ghani, N.T.; Mansour, A.M. Inorg. Chim. Acta, 2011, 373, 249-258.
[http://dx.doi.org/10.1016/j.ica.2011.04.036]
[29]
Eren, B.; Bekdemir, Y. Quim. Nova, 2014, 37, 643-647.
[http://dx.doi.org/10.5935/0100-4042.20140096]
[30]
Paul Hiemenz, C.; Lodge, P.T. Polymer Chemistry, 2nd ed; CRC P: Boca Raton, 2007.
[31]
Buckley, A.; Stuetz, D.; Serad, G. Polybenzimidazoles.Encyclopedia of Polymer Science and Engineering; Kroschwitz, J.I., Ed.; Wiley: New York, 1987, pp. 572-601.
[32]
Amsterdam, D. Susceptibility Testing of antimicrobials in liquid media.Antibiotics in laboratory medicine, 4th ed; Loman, V., Ed.; Williams and Wilkins: Baltimore, MD, 1996, pp. 52-111.
[33]
Clin. Microbiol. Infect., 2003, 9, 1-7.
[34]
Performance Standards for Antimicrobial Susceptibility Testing. 2016.
[35]
Wiegand, I.; Hilpert, K.; Hancock, R.E. Nat. Protoc., 2008, 3(2), 163-175.
[http://dx.doi.org/10.1038/nprot.2007.521] [PMID: 18274517]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy