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Hybrid materials of carbon nanotubes with fluoroalkyl- and alkyl-substituted zinc phthalocyanines

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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.

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References

  1. H. Yakan, M.S. Çavuş, E. Güzel, B.S. Arslan, T. Bakır, H. Muğlu, J. Mol. Struct. 1202, 127259 (2020)

    CAS  Google Scholar 

  2. D. Akyüz, A. Koca, Sens. Actuators 283, 848 (2019)

    Google Scholar 

  3. N. Diab, D.M. Morales, C. Andronescu, M. Masoud, W. Schuhmann, Sens. Actuators 285, 17 (2019)

    CAS  Google Scholar 

  4. 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)

    CAS  Google Scholar 

  5. N.V.S.D.K. Bhupathiraju, W. Rizvi, J.D. Batteas, C.M. Drain, Org. Biomol. Chem. 14, 389 (2016)

    CAS  Google Scholar 

  6. R. Li, X. Zhang, P. Zhu, D.K.P. Ng, N. Kobayashi, J. Jiang, Inorg. Chem. 45, 2327 (2006)

    CAS  Google Scholar 

  7. K. Hesse, D. Schlettwein, J. Electroanal. Chem. 476, 148 (1999)

    CAS  Google Scholar 

  8. Y. Liu, D. Yang, C. Wang, J. Phys. Chem. B 110, 20789 (2006)

    CAS  Google Scholar 

  9. D.D. Klyamer, A.S. Sukhikh, P.O. Krasnov, S.A. Gromilov, N.B. Morozova, T.V. Basova, Appl. Surf. Sci. 372, 79 (2016)

    CAS  Google Scholar 

  10. E.N. Carrión, A. Loas, H.H. Patel, M. Pelmuş, K. Ramji, S.M. Gorun, J. Porphyr. Phthalocyanines 22, 371 (2018)

    Google Scholar 

  11. P.A. Stuzhin, Fluorine in Heterocyclic Chemistry. 5-Membered Heterocycles and Macrocycles (Springer, Cham, 2014)

    Google Scholar 

  12. H. Brinkmann, C. Kelting, S. Makarov, O. Tsaryova, G. Schnurpfeil, D. Wöhrle, D. Schlettwein, Phys. Status Solidi Appl. Mater. Sci. 205, 409 (2008)

    CAS  Google Scholar 

  13. 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)

    CAS  Google Scholar 

  14. N.M. Kuprikova, D.D. Klyamer, A.S. Sukhikh, P.O. Krasnov, I. Mrsic, T.V. Basova, Dyes Pigment 173, 107939 (2020)

    CAS  Google Scholar 

  15. H. Jiang, J. Ye, P. Hu, F. Wei, K. Du, N. Wang, T. Ba, S. Feng, C. Kloc, Sci. Rep. 4, 7573 (2014)

    CAS  Google Scholar 

  16. Z. Bao, A.J. Lovinger, J. Brown, J. Am. Chem. Soc. 120, 207 (1998)

    CAS  Google Scholar 

  17. A. Aktaş, M. Pişkin, M. Durmuş, Z. Biyiklioğlu, J. Lumin. 145, 899 (2014)

    Google Scholar 

  18. A. Aktaş, İ Acar, E.T. Saka, Z. Biyiklioglu, H. Kantekin, J. Incl. Phenom. Macrocycl. Chem. 86, 183 (2016)

    Google Scholar 

  19. S. Tortelli, M. Cavazzini, S. Orlandi, G. Pozzi, I. Pecnikaj, S. Caramori, R. Boaretto, J. Fluor. Chem. 188, 110 (2016)

    CAS  Google Scholar 

  20. T. Qiu, X. Xu, J. Liu, X. Qian, Dyes Pigment 83, 127 (2009)

    CAS  Google Scholar 

  21. M. Harbeck, C. Taşaltın, I. Gürol, E. Musluoğlu, V. Ahsen, Z.Z. Öztürk, Sens. Actuators B 150, 616 (2010)

    CAS  Google Scholar 

  22. T.V. Basova, A. Hassan, P.O. Krasnov, I. Gürol, V. Ahsen, Sens. Actuators B 216, 204 (2015)

    CAS  Google Scholar 

  23. D. Klyamer, A. Sukhikh, S. Gromilov, P. Krasnov, T. Basova, Sensors (Switz.) 18, 1 (2018)

    Google Scholar 

  24. D.P. Jiang, A.D. Lu, Y.J. Li, X.M. Pang, Y.L. Hua, Thin Solid Films 199, 173 (1991)

    CAS  Google Scholar 

  25. X. Ding, H. Xu, L. Zhang, D. Jiang, A. Lu, Mol. Cryst. Liq. Cryst. Sci. Technol. A 337, 481 (1999)

    CAS  Google Scholar 

  26. B. Wang, X. Zhou, Y. Wu, Z. Chen, C. He, X. Zuo, Sens. Actuators B 161, 498 (2012)

    CAS  Google Scholar 

  27. 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)

    CAS  Google Scholar 

  28. 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)

    CAS  Google Scholar 

  29. A.K. Sharma, A. Mahajan, S. Kumar, A.K. Debnath, D.K. Aswal, RSC Adv. 8, 32719 (2018)

    CAS  Google Scholar 

  30. D. Kwak, Y. Lei, R. Maric, Talanta 204, 713 (2019)

    CAS  Google Scholar 

  31. M. Insausti, R. Timmis, R. Kinnersley, M.C. Rufino, Sci. Total Environ. 706, 135124 (2020)

    CAS  Google Scholar 

  32. N.T. Brannelly, J.P. Hamilton-Shield, A.J. Killard, Crit. Rev. Anal. Chem. 46, 490 (2016)

    CAS  Google Scholar 

  33. J.E. Ellis, A. Star, ChemPlusChem 81, 1248 (2016)

    CAS  Google Scholar 

  34. M.S. Polyakov, T.V. Basova, M. Göksel, A. Şenocak, E. Demirbaş, M. Durmuş, B. Kadem, A. Hassan, Synth. Met. 227, 78 (2017)

    CAS  Google Scholar 

  35. A. Şenocak, C. Göl, T.V. Basova, E. Demirbaş, M. Durmuş, H. Al-Sagur, B. Kadem, A. Hassan, Sens. Actuators 256, 853 (2018)

    Google Scholar 

  36. M.M. El-Nahass, Z. El-Gohary, H.S. Soliman, Opt. Laser Technol. 35, 523 (2003)

    CAS  Google Scholar 

  37. K.A. Wepasnick, B.A. Smith, J.L. Bitter, D. Howard Fairbrother, Anal. Bioanal. Chem. 396, 1003 (2010)

    CAS  Google Scholar 

  38. E.N. Kaya, T. Basova, M. Polyakov, M. Durmuş, B. Kadem, A. Hassan, RSC Adv. 5, 91855 (2015)

    CAS  Google Scholar 

  39. B. Wang, X. Zhou, Y. Wu, Z. Chen, C. He, Sens. Actuators B 171–172, 398 (2012)

    Google Scholar 

  40. N.A. Travlou, T.J. Bandosz, Carbon N. Y. 121, 114 (2017)

    CAS  Google Scholar 

  41. Y. Li, B. Wang, Z. Yu, X. Zhou, D. Kang, Y. Wu, Z. Chen, C. He, X. Zhou, RSC Adv. 7, 34215 (2017)

    CAS  Google Scholar 

  42. M.S. Polyakov, T.V. Basova, Macroheterocycles 10, 31 (2017)

    CAS  Google Scholar 

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Acknowledgements

Authors acknowledge Volchek V.V. for analytical (ICP-AES) measurements.

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The work was partially supported by the Ministry of Science and Education of the Russian Federation.

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Correspondence to Tamara Basova.

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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

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