Abstract
This manuscript presents the preparation of polymer layers based on polythiophene (PTh) and its 3-substituted derivatives (substituents 4-(CH3O)C6H4 and 4-(CF3)C6H4 marked as PThOCH3 and PThCF3, respectively) on platinum electrodes by cyclic voltammetry (CV). The polymerization process and the morphology of resulting layers were discussed analysing of CV-voltammograms and scanning electron microscopy (SEM), respectively. Subsequently, the prepared polymers were tested as active/sensitive media of two types of sensors: (i) electrochemical sensor detecting ammonia in aqueous environment, whose response was evaluated by electrochemical impedance spectroscopy (EIS); (ii) chemiresistor detecting NH3 in atmosphere, whose response was evaluated by measurement of resistance. It was found that both the physical (morphology, homogeneity, relative thickness) and receptor properties of the polymer layer deposited on electrode surface are significantly affected by the nature of substituent attached to the thiophene ring. The mutual context of ammonia detection in both environments is discussed.
Graphical Abstract
Similar content being viewed by others
References
Wang Y, Liu A, Han Y, Li T (2020) Sensors based on conductive polymers and their composites: a review. Polym Int 69:7–17. https://doi.org/10.1002/pi.5907
Wong YC, Ang BC, Haseeb ASMA, Baharuddin AA, Wong YH (2019) Review - conducting polymers as chemiresistive gas sensing materials: a review. J Electrochem Soc 167:037503. https://doi.org/10.1149/2.0032003JES
Lan R, Tao S (2014) Ammonia as a suitable fuel for fuel cells. Front Energy Res 2:35. https://doi.org/10.3389/fenrg.2014.00035
Appl M (2011) Ammonia, 1. Introdution. In: Ullmann's encyclopedia of industrial chemistry, 7th edn. Wiley-VCH, Germany https://doi.org/10.1002/14356007.a02_143.pub3
Meulenbelt J (2007) Ammon Med 35:583–584. https://doi.org/10.1016/j.mpmed.2007.08.004
Ammonia exposure limits in the United Kingdom: https://www.hse.gov.uk/pUbns/priced/eh40.pdf. Accessed 20 Apr 2020
Ammonia exposure limits in the Czech Republic: https://www.irz.cz/repository/latky/amoniak.pdf. Accessed 15 Apr 2020
https://www.tfi.org/sites/default/files/documents/HealthAmmoniaFINAL.pdf. Accessed 7 Apr 2020
https://assets.publishing.service.gov.uk/government/uploads/system/uploads/attachment_data/file/455704/Ammonia_TO_PHE_240815.pdf. Accessed 20 Apr 2020
Aarya S, Kumar Y, Chahota RK (2020) Recent advances in materials, parameters, performance and technology in ammonia sensors: a review. J Inorg Organomet Polym Mater 30:269–290. https://doi.org/10.1007/s10904-019-01208-x
Timmer B, Olthuis W, Avd B (2005) Ammonia sensors and their applications - a review. Sens Actuators B Chem 107:666–677. https://doi.org/10.1016/j.snb.2004.11.054
Tanguy NR, Thompson M, Yan N (2018) A review on advances in application of polyaniline for ammonia detection. Sens Actuators B Chem 257:1044–1064. https://doi.org/10.1016/j.snb.2017.11.008
Šetka M, Drbohlavová J, Hubálek J (2017) Nanostructured polypyrrole-based ammonia and volatile organic compound sensors. Sensors 17:562. https://doi.org/10.3390/s17030562
Guernion NJL, Hayes W (2004) 3- and 3,4-substituted pyrroles and thiophenes and their corresponding polymers - a review. Curr Org Chem 8:637–651. https://doi.org/10.2174/1385272043370771
Li C, Shi G (2013) Polythiophene-based optical sensors for small molecules. ACS App Mater Interfaces 5:4503–4510. https://doi.org/10.1021/am400009d
Huynh T-P, Sharma PS, Sosnowska M, D’Souza F, Kutner W (2015) Functionalized polythiophenes: recognition materials for chemosensors and biosensors of superior sensitivity, selectivity, and detectability. Prog Polym Sci 47:1–25. https://doi.org/10.1016/j.progpolymsci.2015.04.009
Kwak D, Lei Y, Maric R (2019) Ammonia gas sensors: a comprehensive review. Talanta 204:713–730. https://doi.org/10.1016/j.talanta.2019.06.034
Yoon H (2013) Current trends in sensors based on conducting polymer nanomaterials. Nanomaterials 3:524–549. https://doi.org/10.3390/nano3030524
Bai H, Shi G (2007) Gas sensors based on conducting polymers. Sensors 7:267–307. https://doi.org/10.3390/s7030267
Chang A, Peng Y, Li Z, Yu X, Hong K, Zhou S, Vu W (2016) Assembly of polythiophenes on responsive polymer microgels for the highly selective detection of ammonia gas. Polym Chem 7:3179–3188. https://doi.org/10.1039/c5py02014j
Liao F, Yin S, Toney MF, Subramanian V (2010) Physical discrimination of amine vapor mixtures using polythiophene gas sensor arrays. Sens Actuators B 150:254–263. https://doi.org/10.1016/j.snb.2010.07.006
Al-Refai H, Ganash AA, Hussein A (2021) Polythiophene and its derivatives-based nanocomposites in electrochemical sensing: a mini review. Mater Today Communs 26:101935. https://doi.org/10.1016/j.mtcomm.2020.101935
Faisal M, Harraz FA, Al-Salami AE, Al-Sayari SA, Al-Hajry A, Al-Assiri MS (2018) Polythiophene/ZnO nanocomposite-modified glassy carbon electrode as efficient electrochemical hydrazine sensor. Mater Chem Phys 214:126–134. https://doi.org/10.1016/j.matchemphys.2018.04.085
Vijeth H, Ashokkumar SP, Yesappa L, Vandana M, Dvendrappa H (2019) Camphor sulfonic acid surfactant assited polythiophene nanocomposite for efficient electrochemical hydrazine sensor. Mater Res Express 6:125375. https://doi.org/10.1088/20531591/ab5ef5
Shishkanova TV, Štěpánková N, Tlustý M, Tobrman T, Jurásek B, Kuchař M, Trchová M, Fitl P, Vrňata M (2021) Electrochemically oxidized 15-crown-5 substituted thiophene and host-guest interaction with new psychoactive substances. Electrochim Acta 373:137862. https://doi.org/10.1016/j.electacta.2021.137862
Shi S, Meng G, Szostak M (2016) Synthesis of biaryls through nickel-catalyzed Suzuki-Miyaura coupling of amides by carbon–nitrogen bond cleavage. Angew Chem Int Ed 55:6959–6963. https://doi.org/10.1002/anie.201601914
Budén ME, Guastavino JF, Rossi RA (2013) Room-temperature photoinduced direct C-H-Arylation via base-promoted homolytic aromatic substitution. Org Lett 15:1174–1177. https://doi.org/10.1021/ol3034687
Volochanskyi O, Švecová M, Prokopec V (2019) Detection and identification of medically important alkaloids using the surface-enhanced Raman scattering spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc 207:143–149. https://doi.org/10.1016/j.saa.2018.09.009
Guerrero DJ, Ren X, Ferraris JP (1994) Preparation and characterization of poly(3-arylthiophene)s. Chem Mater 6:1437–1443.
Dogbéavou R, El-Mehdi N, Naudin E, Breau L, Bélanger D (1997) Synthesis and electrochemical polymerization of poly [3-(1-naphthylthiophene)]. Synth Met 84:207–208. https://doi.org/10.1016/S0379-6779(97)80715-1
Siddekha A, Nizam A, Pasha MA (2011) An efficient and simple approach for the synthesis of pyranopyrazoles using imidazole (catalytic) in aqueous medium, and the vibrational spectroscopic studies on 6-amino-4-(4′-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole using density functional theory. Spectrochim Acta A Mol Biomol Spectrosc 81(1):431–440. https://doi.org/10.1016/j.saa.2011.06.033
Subbulakshmi RR, Palanichamy E, Arivazhagan M, Manivel S (2019) Theoretical studies on molecular structure and vibrational spectra of 2,4-difluoro-1-methoxy benzene and 1-chloro-3-methoxy benzene. Int J Sci Res Phys Appl Sci 7(3):34–48. https://doi.org/10.26438/ijsrpas/v7i3.3448
Hangarter CM, Chartuprayoon N, Hernández SC, Choa Y, Myung NV (2013) Hybridized conducting polymer chemiresistive nano-sensors. Nano Today 8:39–55. https://doi.org/10.1016/j.nantod.2012.12.005
Besar K, Yang S, Guo X, Huang W, Rule AM, Breysse PN, Kymissis IJ, Katz HE (2014) Printable ammonia sensor based on organic field effect transistor. Org Electron 15:3221–3230. https://doi.org/10.1016/j.orgel.2014.08.023
Marr I, Moos R (2017) Resistive NOx dosimeter to detect very low NOx concentrations—proof-of-principle and comparison with classical sensing devices. Sens Actuators B Chem 248:848–855. https://doi.org/10.1016/j.snb.2016.12.112
Smith MK, Jensen KE, Pivak PA, Mirica KA (2016) Direct self-assembly of conductive nanorods of metal–organic frameworks into chemiresistive devices on shrinkable polymer films. Chem Mater 28:5264–5268. https://doi.org/10.1021/acs.chemmater.6b02528
Zhu R, Desroches M, Yoon B, Swager TM (2017) Wireless oxygen sensors enabled by Fe (II)-polymer wrapped carbon nanotubes. ACS Sensors 2:1044–1050. https://doi.org/10.1021/acssensors.7b00327
Na W, Kim J, Kim YK, Kim SG, Jang J (2020) Fluorination of shape-controlled porous carbon nanoweb layers for ammonia gas sensor applications. Carbon 165:185–195. https://doi.org/10.1016/j.carbon.2020.04.085
Makhloufi C, Roizard D, Favre E (2013) Reverse selective NH3/CO2 permeation in fluorinated polymers using membrane gas separation. J Membr Sci 441:63–72. https://doi.org/10.1016/j.memsci.2013.03.048
Chabukswar VV, Pethkar S, Athawale AA (2001) Acrylic acid doped polyaniline as an ammonia sensor. Sens Actuators B Chem 77:657–663. https://doi.org/10.1016/S0925-4005(01)00780-8
Virji S, Huang J, Kaner RB, Weiller BH (2004) Polyaniline nanofiber gas sensors: examination of response mechanisms. Nano Lett 4:491–496. https://doi.org/10.1021/nl035122e
Hernandez SC, Chaudhuri D, Chen W, Myung NV, Mulchandani A (2007) Single polypyrrole nanowire ammonia gas sensor. Electroanalysis 19:2125–2130. https://doi.org/10.1002/elan.200703933
Patois T, Sanchez J-B, Berger F, Rauch J-Y, Fievet P, Lakard B (2012) Ammonia gas sensors based on polypyrrole films: influence of electrodeposition parameters. Sens Actuators B Chem 171–172:431–439. https://doi.org/10.1016/j.snb.2012.05.005
Dunst KJ, Cysewska K, Kalinowski P, Jasiński P (2016) Polypyrrole based gas sensor for ammonia detection. IOP Conf Ser Mater Sci Eng 104:012028. https://doi.org/10.1088/1757-899X/104/1/012028
Oudenhoven JFM, Knoben W, van Schaijk R (2015) Electrochemical detection of ammonia using a thin ionic liquid film as the electrolyte. Procedia Eng 120:983–986. https://doi.org/10.1016/j.proeng.2015.08.636
Zhang L, Liu T, Ren R, Zhang J, He D, Zhao C, Suo H (2020) In situ synthesis of hierarchical platinum nanosheets-polyaniline array on carbon cloth for electrochemical detection of ammonia. J Hazard Mater 392:122342. https://doi.org/10.1016/j.jhazmat.2020.122342
Zhang L, Wei L, Liu J, Gu J, Suo H, Zhao C (2022) One step and in situ synthesis of Ni foam-supported Pt-Ni(OH)2 nanosheets as electrochemical sensor for ammonia–nitrogen detection. Mater Lett 318:132197. https://doi.org/10.1016/j.matlet.2022.132197
Prabhu CPK, Aralekallu S, Palanna M, Palanna M, Sajjan V, Renuka B, Sannegowda LK (2022) Novel polymeric zinc phthalocyanine for electro-oxidation and detection of ammonia. J Appl Electrochem 52:325–338. https://doi.org/10.1007/s10800-021-01640-3
Tadi KK, Pal S, Narayanan TN (2016) Fluorographene based ultrasensitive ammonia sensor. Sci Rep 6:25221. https://doi.org/10.1038/srep25221
Morakchi ZK, Zazoua A, Saad S, Kherrat R, Jaffrezic-Renault N (2008) Characterization of ammonium ion - sensitive membranes in solution with electrochemical impedance spectroscopy. Mater Sci Eng C 28:1020–1023. https://doi.org/10.1016/j.msec.2007.10.081
Zhybak MT, Vagin MY, Beni V, Liu X, Dempsey E, Turner APF, Korpan YI (2016) Direct detection of ammonium ion by means of oxygen electrocatalysis at a copper-polyaniline composite on a screen-printed electrode. Microchim Acta 183:1981–1987. https://doi.org/10.1007/s00604-016-1834-3
Deng AP, Cheng JT, Huang HJ (2002) Application of a polyaniline based ammonium sensor for the amperometric immunoassay of a urease conjugated Tal 1 protein. Anal Chim Acta 461:49–55
Saiapina OY, Kharchenko SG, Vishnevskii SG, Pyeshkova VM, Kalchenko VI, Dzyadevych SV (2016) Development of conductometric sensor based on 25, 27-di-(5-thio-octyloxy)calix [4] arene-crown-6 for determination of ammonium. Nanoscale Res Lett 11:105–115. https://doi.org/10.1186/s11671-016-1317-9
Acknowledgements
Authors are grateful to S. Effenberková for assistance in electrochemical measurements, M. Trchová for spectroscopic measurements, professor P. Matějka for discussion of spectroscopic results. This work was supported by a specific University research grant (Ministry of Education, Youth and Sports of the Czech Republic UCT Prague, CZ, 402850061). M. Vrňata, J. Otta and P. Fitl acknowledge the support from Czech Science Foundation (GAČR) project No. 22-14886S and Ministry of Education, Youth and Sports of the Czech Republic project No. 8F21008 and project No. JP22420 from the International Visegrad Fund.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflicts of interest.
Additional information
Handling Editor: Chris Cornelius.
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Shishkanova, T.V., Tobrman, T., Otta, J. et al. Substituted polythiophene-based sensor for detection of ammonia in gaseous and aqueous environment. J Mater Sci 57, 17870–17882 (2022). https://doi.org/10.1007/s10853-022-07694-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10853-022-07694-8