Abstract
In this work, hybrid materials of single-walled carbon nanotubes (SWCNT) noncovalently functionalized with fluoroalkyl- (SWCNT/ZnPc-CF) and alkyl- (SWCNT/ZnPc-CH) substituted zinc(II) phthalocyanines were prepared. The effect of fluorination of the substituents in phthalocyanine macrocycle on the functionalization degree of carbon nanotubes and sensor response to ammonia was investigated. It was shown that the type of substituents in the phthalocyanine macrocycle showed noticeable effect both on the degree of functionalization of carbon nanotubes and on the sensing performance of the investigated hybrids. The amount of phthalocyanine molecules adsorbed on SWCNT walls was shown to be 1.5 times higher in the SWCNT/ZnPc-CH hybrid. The SWCNT/ZnPc-CF layer exhibited 2 times less chemiresistive sensor response to ammonia than SWCNT/ZnPc-CH, while its sensor response was more stable at 70% relative humidity.
Similar content being viewed by others
Data availability
Not applicable.
Code availability
Not applicable.
References
H. Yakan, M.S. Çavuş, E. Güzel, B.S. Arslan, T. Bakır, H. Muğlu, J. Mol. Struct. 1202, 127259 (2020)
D. Akyüz, A. Koca, Sens. Actuators 283, 848 (2019)
N. Diab, D.M. Morales, C. Andronescu, M. Masoud, W. Schuhmann, Sens. Actuators 285, 17 (2019)
Y. Wang, H. Shan, X. Sun, L. Dong, Y. Feng, Q. Hu, W. Ye, V.A.L. Roy, J. Xu, Z.-X. Xu, Org. Electron. 55, 15 (2018)
N.V.S.D.K. Bhupathiraju, W. Rizvi, J.D. Batteas, C.M. Drain, Org. Biomol. Chem. 14, 389 (2016)
R. Li, X. Zhang, P. Zhu, D.K.P. Ng, N. Kobayashi, J. Jiang, Inorg. Chem. 45, 2327 (2006)
K. Hesse, D. Schlettwein, J. Electroanal. Chem. 476, 148 (1999)
Y. Liu, D. Yang, C. Wang, J. Phys. Chem. B 110, 20789 (2006)
D.D. Klyamer, A.S. Sukhikh, P.O. Krasnov, S.A. Gromilov, N.B. Morozova, T.V. Basova, Appl. Surf. Sci. 372, 79 (2016)
E.N. Carrión, A. Loas, H.H. Patel, M. Pelmuş, K. Ramji, S.M. Gorun, J. Porphyr. Phthalocyanines 22, 371 (2018)
P.A. Stuzhin, Fluorine in Heterocyclic Chemistry. 5-Membered Heterocycles and Macrocycles (Springer, Cham, 2014)
H. Brinkmann, C. Kelting, S. Makarov, O. Tsaryova, G. Schnurpfeil, D. Wöhrle, D. Schlettwein, Phys. Status Solidi Appl. Mater. Sci. 205, 409 (2008)
R.G. Parkhomenko, A.S. Sukhikh, D.D. Klyamer, P.O. Krasnov, S. Gromilov, B. Kadem, A.K. Hassan, T.V. Basova, J. Phys. Chem. C 121, 1200 (2017)
N.M. Kuprikova, D.D. Klyamer, A.S. Sukhikh, P.O. Krasnov, I. Mrsic, T.V. Basova, Dyes Pigment 173, 107939 (2020)
H. Jiang, J. Ye, P. Hu, F. Wei, K. Du, N. Wang, T. Ba, S. Feng, C. Kloc, Sci. Rep. 4, 7573 (2014)
Z. Bao, A.J. Lovinger, J. Brown, J. Am. Chem. Soc. 120, 207 (1998)
A. Aktaş, M. Pişkin, M. Durmuş, Z. Biyiklioğlu, J. Lumin. 145, 899 (2014)
A. Aktaş, İ Acar, E.T. Saka, Z. Biyiklioglu, H. Kantekin, J. Incl. Phenom. Macrocycl. Chem. 86, 183 (2016)
S. Tortelli, M. Cavazzini, S. Orlandi, G. Pozzi, I. Pecnikaj, S. Caramori, R. Boaretto, J. Fluor. Chem. 188, 110 (2016)
T. Qiu, X. Xu, J. Liu, X. Qian, Dyes Pigment 83, 127 (2009)
M. Harbeck, C. Taşaltın, I. Gürol, E. Musluoğlu, V. Ahsen, Z.Z. Öztürk, Sens. Actuators B 150, 616 (2010)
T.V. Basova, A. Hassan, P.O. Krasnov, I. Gürol, V. Ahsen, Sens. Actuators B 216, 204 (2015)
D. Klyamer, A. Sukhikh, S. Gromilov, P. Krasnov, T. Basova, Sensors (Switz.) 18, 1 (2018)
D.P. Jiang, A.D. Lu, Y.J. Li, X.M. Pang, Y.L. Hua, Thin Solid Films 199, 173 (1991)
X. Ding, H. Xu, L. Zhang, D. Jiang, A. Lu, Mol. Cryst. Liq. Cryst. Sci. Technol. A 337, 481 (1999)
B. Wang, X. Zhou, Y. Wu, Z. Chen, C. He, X. Zuo, Sens. Actuators B 161, 498 (2012)
S.M. Hong, A.K. Mutyala, M.J. Cha, J.H. Seo, Y.A. Kang, J.S. Park, Bull. Korean Chem. Soc. 38, 1190 (2017)
B. Yuan, H. Wang, J. Cai, Y. Peng, Y. Niu, H. Chen, L. Bai, S. Zhang, J. Jin, L. Liu, C. Xu, Sens. Actuators B 288, 180 (2019)
A.K. Sharma, A. Mahajan, S. Kumar, A.K. Debnath, D.K. Aswal, RSC Adv. 8, 32719 (2018)
D. Kwak, Y. Lei, R. Maric, Talanta 204, 713 (2019)
M. Insausti, R. Timmis, R. Kinnersley, M.C. Rufino, Sci. Total Environ. 706, 135124 (2020)
N.T. Brannelly, J.P. Hamilton-Shield, A.J. Killard, Crit. Rev. Anal. Chem. 46, 490 (2016)
J.E. Ellis, A. Star, ChemPlusChem 81, 1248 (2016)
M.S. Polyakov, T.V. Basova, M. Göksel, A. Şenocak, E. Demirbaş, M. Durmuş, B. Kadem, A. Hassan, Synth. Met. 227, 78 (2017)
A. Şenocak, C. Göl, T.V. Basova, E. Demirbaş, M. Durmuş, H. Al-Sagur, B. Kadem, A. Hassan, Sens. Actuators 256, 853 (2018)
M.M. El-Nahass, Z. El-Gohary, H.S. Soliman, Opt. Laser Technol. 35, 523 (2003)
K.A. Wepasnick, B.A. Smith, J.L. Bitter, D. Howard Fairbrother, Anal. Bioanal. Chem. 396, 1003 (2010)
E.N. Kaya, T. Basova, M. Polyakov, M. Durmuş, B. Kadem, A. Hassan, RSC Adv. 5, 91855 (2015)
B. Wang, X. Zhou, Y. Wu, Z. Chen, C. He, Sens. Actuators B 171–172, 398 (2012)
N.A. Travlou, T.J. Bandosz, Carbon N. Y. 121, 114 (2017)
Y. Li, B. Wang, Z. Yu, X. Zhou, D. Kang, Y. Wu, Z. Chen, C. He, X. Zhou, RSC Adv. 7, 34215 (2017)
M.S. Polyakov, T.V. Basova, Macroheterocycles 10, 31 (2017)
Acknowledgements
Authors acknowledge Volchek V.V. for analytical (ICP-AES) measurements.
Funding
The work was partially supported by the Ministry of Science and Education of the Russian Federation.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Bonegardt, D., Klyamer, D., Köksoy, B. et al. Hybrid materials of carbon nanotubes with fluoroalkyl- and alkyl-substituted zinc phthalocyanines. J Mater Sci: Mater Electron 31, 11021–11028 (2020). https://doi.org/10.1007/s10854-020-03650-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10854-020-03650-x