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Influence of metals and substituent on interaction behaviour of metal phthalocyanines combinations with organic vapors

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Abstract

In the present work, we have studied the interaction behaviour of various metal phthalocyanines (MPcs); functionalized copper and nickel Phthalocyanines (CuPcS and NiPcS) and Aluminium Phthalocyanine hydroxide (AlPcOH) and their combinations dispersed in sol–gel glass towards organic vapors. Addition of AlPcOH in MPcs combinations has enabled faster response-recovery times with better stability of MPcs composites under ambient conditions. The concept of primary and secondary charge transfer mechanism coupled with steric hindrance effect explains the varied sensing responses of MPcs. Amendment in the sensing responses towards organic vapors has been observed after combining MPcs. Significant shifts in Q bands of MPcs after DEA exposure and distortions observed in central metal ion coordinated vibration bands confirm the primary participation of MPcs during charge transfer with organic vapors. Consistencies of the optical and spectroscopic results with electrical sensing results confirm better sensitivity of MPcs towards DEA vapors as compared to methanol under ambient conditions.

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References

  1. Z. Ahmad, M.H. Sayyad, M. Yaseen, K.C. Aw, M.M. Tahir, M. Alie, Potential of 5,10,15,20-Tetrakis(3’,5’-di-tertbutylphenyl) porphyrinatocopper(II) for a multifunctional sensor. Sens. Actuators B 155, 81–85 (2011)

    Article  CAS  Google Scholar 

  2. P. Peumans, S.R. Forrest, Very high efficiency double hetrostructure copper pthalocyanine/C60 photovoltaic cells. Appl. Phys. Lett. 79, 126–128 (2001)

    Article  CAS  Google Scholar 

  3. T. Sekrafi, B. Bouricha, Z. Denden, S. Tascu, A. Labidi, H. Nasri, C. Dridi, Development of cost-effective, selective and stable room temperature methanol sensor. IEEE Sens. J. 21, 2589–2596 (2021)

    Article  CAS  Google Scholar 

  4. M. Evyapan, A.D.F. Dunbar, Controlling surface adsorption to enhance the selectivity of porphyrin based gas sensors. Appl. Surf. Sci. 362, 191–201 (2016)

    Article  CAS  Google Scholar 

  5. M. Evyapan, A.D.F. Dunbar, Improving the selectivity of a free base tetraphenylporphyrin based gas sensor for NO2 and carboxylic acid vapors. Sens. Actuators B 206, 74–83 (2015)

    Article  CAS  Google Scholar 

  6. E. Kakı, N. Gögsu, A. Altındal, B. Salih, Ö. Bekaroğlu, Synthesis, characterization and VOCs adsorption kinetics of diethylstilbestrol-substituted metallophthalocyanines. J. Porphyr Phthalocyanines 23, 166–174 (2019)

    Article  Google Scholar 

  7. R. Ridhi, S. Sachdeva, G.S.S. Saini, S.K. Tripathi, Sensing response of copper phthalocyanine salt dispersed glass with organic vapours. AIP. Conf. Proc. 1728, 020290 (2016)

    Article  Google Scholar 

  8. G.P. Shaposhnikov, V.E. Maizlish, V.P. Kulinich, Bifunctional octasubstituted phthalocyanines. Synthesis and properties. Russ. J. Gen. Chem. 77, 138–146 (2007)

    Article  CAS  Google Scholar 

  9. A. Aykanat, Z. Meng, G. Benedetto, K.A. Mirica, Molecular engineering of multifunctional metallophthalocyanine-containing framework materials. Chem. Mater. 32, 5372–5409 (2020)

    Article  CAS  Google Scholar 

  10. M.S. Fakir, Z. Ahmad, K. Sulaiman, Modification of optical band gap and surface morphology of NiTsPc thin films. Chin. Phys. Lett. 12(126802), 1–5 (2012)

    Google Scholar 

  11. M. Shah, M. Sayyad, K.S. Karimov, F. Wahab, Electrical characterization of the ITO/NiPc/PEDOT: PSS junction diode. J. Phys. D: Appl. Phys. 43, 405104 (2010)

    Article  Google Scholar 

  12. G.S.S. Saini, S.D. Dogra, G. Singh, S.K. Tripathi, S. Kaur, V. Sathe, B.C. Choudhary, Effects of chemical analytes on zinc tetraphenylporphine thin films studied by vibrational spectroscopy and density functional theory. Vib. Spectrosc. 61, 188–198 (2012)

    Article  CAS  Google Scholar 

  13. R. Ridhi, G.S.S. Saini, S.K. Tripathi, Study of interaction mechanism of metal phthalocyanines dispersed sol-gel glasses with chemical vapors. Sens. Actuators B 255, 1849–1868 (2018)

    Article  CAS  Google Scholar 

  14. R. Ridhi, G.S.S. Saini, S.K. Tripathi, Sensing of organic vapors by sulfonated copper phthalocyanine salt thin films. Mat. Focus 6, 386–393 (2017)

    Article  Google Scholar 

  15. R. Ridhi, G.S.S. Saini, S.K. Tripathi, Sensing of volatile organic compounds by copper phthalocyanine thin films. Mat. Res. Xpress 4(025102), 1–13 (2017)

    Google Scholar 

  16. K. Arnold, T.S. Balaban, M.N. Blom, O.T. Ehrler, S. Gilb, O. Hampe, J.E.V. Lier, J.M. Weber, M.M. Kappes, Electron autodetachment from isolated nickel and copper phthalocyanine-tetrasulfonate tetraanions: isomer specific rates. J. Phys. Chem. A 107, 794–803 (2003)

    Article  CAS  Google Scholar 

  17. M.P. Polat, D. Akyüz, H.Y. Yenilmez, A. Koca, A. Altındal, Z.A. Bayır, Sensing alcohol vapours with novel unsymmetrically substituted metallophthalocyanines. Dalton Trans. 48, 9194–9204 (2019)

    Article  Google Scholar 

  18. S.N. Işık, G.K. Karaoğlan, B.C. Ömür, A. Altındal, G.G. Köse, Synthesis, characterization and ethanol sensing properties of carboxylic acid-terminated naphthoxy substituted phthalocyanines. Synth. Met. 246, 7–15 (2018)

    Article  Google Scholar 

  19. J.W. Namgoong, H.M. Kima, S.H. Kim, S.B. Yuk, J. Choi, J.P. Kim, Synthesis and characterization of metal phthalocyanine bearing carboxylic acid anchoring groups for nanoparticle dispersion and their application to color filters. Dyes Pigm. 184, 108737 (2021)

    Article  CAS  Google Scholar 

  20. A.M. Paoletti, G. Pennesi, G. Rossi, A. Generosi, B. Paci, V.R. Albertini, Titanium and ruthenium phthalocyanines for NO2 sensors: a mini-review. Sensors 9, 5277–5297 (2009)

    Article  CAS  Google Scholar 

  21. T. Basova, V. Plyashkevich, A. Hassan, A.G. Gürek, G. Gümüs, V. Ahsen, Phthalocyanine films as active layers of optical sensors for pentachlorophenol detection. Sens. Actuators B 139, 557–562 (2009)

    Article  CAS  Google Scholar 

  22. S.Z. Topal, Ü. İşci, U. Kumru, D. Atilla, A.G. Gürek, C. Hirel, M. Durmuş, J.B. Tommasino, D. Luneau, S. Berber, F. Dumoulin, V. Ahsen, Modulation of the electronic and spectroscopic properties of Zn(II) phthalocyanines by their substitution pattern. Dalton Trans. 43, 6897–6908 (2014)

    Article  CAS  Google Scholar 

  23. X. Liu, C. Qi, T. Bing, X. Cheng, D. Shangguan, Highly selective phthalocyanine-thymine conjugate sensor for Hg2+ based on target induced aggregation. Anal. Chem. 81, 3699–3704 (2009)

    Article  CAS  Google Scholar 

  24. M. Evyapan, B. Kadem, T.V. Basova, I.V. Yushina, A.K. Hassan, Study of the sensor response of spun metal phthalocyanine films to volatile organic vapors using surface plasmon resonance. Sens. Actuators B 236, 605–613 (2016)

    Article  CAS  Google Scholar 

  25. Y. Açıkbaşa, M. Evyapan, T. Ceyhan, R. Çapan, Ö. Bekaroğlu, Characterization and organic vapor sensing properties of Langmuir-Blodgett film using a new three oxygen-linked phthalocyanine incorporating lutetium. Sens. Actuators B 135, 426–429 (2009)

    Article  Google Scholar 

  26. Z.H. Wen, T.F. Kang, Determination of nitrite using sensors based on nickel phthalocyanine polymer modified electrodes. Talanta 62, 351–355 (2004)

    Article  CAS  Google Scholar 

  27. T. Pustelny, J. Ignac-Nowicka, B. Jarzabek, A. Burian, Optical investigations on layered metalphthalocyanines nanostructures affected by NO2 applying the surface Plasmon resonance method. Opt. Appl. 34, 563–572 (2004)

    CAS  Google Scholar 

  28. T.V. Basova, E.K. Kol’tsov, I.K. Igumenov, Spectral investigation of interaction of copper phthalocyanine with nitrogen dioxide. Sens. Actuators B 105, 259–265 (2005)

    Article  CAS  Google Scholar 

  29. G.S.S. Saini, S. Singh, S. Kaur, R. Kumar, V. Sathe, S.K. Tripathi, Zinc phthalocyanine thin film and chemical analyte interaction studies by density functional theory and vibrational techniques. J. Phys. Condens. Matter 21, 1–9 (2009)

    Article  Google Scholar 

  30. R. Pandeeswari, B.G. Jeyaprakash, High sensing response of ß-Ga2O3thin film towards ammoniavapors: influencing factors at room temperature. Sens. Actuators B 195, 206–214 (2014)

    Article  CAS  Google Scholar 

  31. Y. Açıkbaşa, M. Evyapan, T. Ceyhan, R. Çapan, Ö. Bekaroğlu, Characterisation of Langmuir-Blodgett films of new multinuclear copper and zinc phthalocyanines and their sensing properties to volatile organic vapours. Sens. Actuators B 123, 1017–1024 (2007)

    Article  Google Scholar 

  32. R. Ridhi, G.S.S Saini, S.K. Tripathi, Study of interaction mechanism of chemical vapors in copper phthalocyanine sol-gel glass, Book: Nanotechnology: Novel Perspectives and Prospects. ISBN-13: 978-93-39221-09-6, ISBN-10: 93-39221-09-5, pp 302–308

  33. T.M. Tsubone, G. Braga, B.H. Vilsinski, A.P. Gerola, N. Hioka, A.L. Tessaro, W. Caetano, Aggregation of aluminum phthalocyanine hydroxide in water/ethanol mixtures. J. Braz. Chem. Soc. 25, 890–897 (2014)

    CAS  Google Scholar 

  34. B. Popanda, M. Środa, Porphyrin and phthalocyanine as materials for glass coating—structure and properties. Adv. Glass Res. 16426, 241–317 (2023)

    Article  Google Scholar 

  35. L. Zan, J.W. Rui, W. Xiaohong, S. Yunbo, Preparation and characterization of novel octa-iso- pentyloxymetallophthalocyanines(M= Pb, Ni, Cu) gas sensors. Int. J. Electrochem. Sci. 8, 7044–7052 (2013)

    Google Scholar 

  36. M. Wang, K. Torbensen, D. Salvatore, S. Ren, D. Joulié, F. Dumoulin, D. Mendoza, B.L. Kaiser, U. Işci, C.P. Berlinguette, M. Robert, CO2 electrochemical catalytic reduction with a highly active cobalt phthalocyanine. Nat. Commun. 3602, 1–8 (2019)

    Google Scholar 

  37. R. Ridhi, S. Singh, G.S.S. Saini, S.K. Tripathi, Comparison of interaction mechanisms of copper phthalocyanine and nickel phthalocyanine thin films with chemical vapors. J. Phys. Chem. Solids 115, 119–126 (2018)

    Article  CAS  Google Scholar 

  38. R. Ridhi, J. Kang, G.S.S. Saini, S.K. Tripathi, Spectroscopic interaction studies of substituted and unsubstituted copper phthalocyanine with adsorbed organic vapours. AIP Conf. Proc. 1953(030172), 1–4 (2018)

    Google Scholar 

  39. E. Ahmetali, H.P. Karaoğlu, Y. Urfa, A. Altındal, M.B. Koçak, A series of asymmetric zinc (II) phthalocyanines containing fluoro and alkynyl groups: synthesis and examination of humidity sensing performance by using QCM based sensor. Mater. Chem. Phys. 254, 123477 (2020)

    Article  CAS  Google Scholar 

  40. G.S.S. Saini, S.D. Dogra, K. Sharma, S. Singh, S.K. Tripathi, V. Sathe, R.K. Singh, Experimental and density functional theoretical study of the effects of chemical vapors on the vibrational spectra of nickel phthalocyanine thin films. Vib. Spectrosc. 57, 61–71 (2011)

    CAS  Google Scholar 

  41. M.E. Azim-Araghi, S. Haji Mirza Mohamadi, Z. Bisadi, Morphology, optical and AC electrical properties of copper phthalocyanine thin films. Acta Phys. Pol. A 125, 87–92 (2014)

    Article  Google Scholar 

  42. F.S.D. Torre, J.R.D. Rosa, B.I. Kharisov, C.J.L. Ortiz, Preparation and characterization of Cu and Ni on alumina supports and their use in the synthesis of low-temperature metal-phthalocyanine using a parallel-plate reactor. Materials 6, 4324–4344 (2013)

    Article  Google Scholar 

  43. R. Ridhi, G.S.S. Saini, S.K. Tripathi, Study of the effect of methanol vapors on copper phthalocyanine salt sol-gel glass. J. Basic Appl. Eng. Res. 13, 47–49 (2014)

    Google Scholar 

  44. R. Ridhi, S. Gautam, G.S. Saini, S.K. Tripathi, J.S. Rawat, P. Jha, Study of the effect of orbital on interaction behaviour of SWCNT- metal phthalocyanines composites with ammonia gas. Sens. Actuators B 337, 129767 (2021)

    Article  CAS  Google Scholar 

  45. R. Ridhi, A. Chouksey, S. Gautam, J.S. Rawat, P. Jha, Study of the effect of flow rate and decomposition temperature on sensing of ammonium nitrate by carbon nanotubes. Sens. Actuators B 334, 129658 (2021)

    Article  CAS  Google Scholar 

  46. J. Peng, L. Weiab, Y. Liuc, W. Zhugea, Q. Huanga, W. Huanga, G. Xianga, C. Zhang, Novel porous iron phthalocyanine based metal–organic framework electrochemical sensor for sensitive vanillin detection. RSC Adv. 10, 36828–36835 (2020)

    Article  CAS  Google Scholar 

  47. I. Musa, G. Raffin, M. Hangouet, M. Martin, A. Alcacer, N. Zine, F. Bellagambi, N.J. Renault, A. Errachid, Development of a chitosan/nickel phthalocyanine composite based conductometric micro-sensor for methanol detection. Electroanalysis 34, 1338–1347 (2022)

    Article  CAS  Google Scholar 

  48. D. Klyamer, R. Shutilov, T. Basova, Recent advances in phthalocyanine and porphyrin-based materials as active layers for nitric oxide chemical sensors. Sensors 22(3), 895 (2022). https://doi.org/10.3390/s22030895

    Article  CAS  Google Scholar 

  49. A. Yazici, N. Dalbula, A. Altındal, B. Salih, Ö. Bekaroğlu, Ethanol sensing property of novel phthalocyanines substituted with 3,4-dihydroxy-3-cyclobuten-1,2-dione. Sensor. Actuators B 202, 14–22 (2014)

    Article  CAS  Google Scholar 

  50. S. Singh, S.K. Tripathi, G.S.S. Saini, Optical and infrared spectroscopic studies of chemical sensing by copper phthalocyanine thin films. Mater. Chem. Phys. 112, 793–797 (2008)

    Article  CAS  Google Scholar 

  51. H. Banimuslem, A. Hassan, T. Basova, A.A. Esenpınar, S. Tuncel, M. Durmuş, A.G. Gürek, V. Ahsen, Dye-modified carbon nanotubes for the optical detection of amines vapors. Sens. Actuators B 207, 224–234 (2015)

    Article  CAS  Google Scholar 

  52. R. Ridhi, S. Gautam, G.S. Saini, S.K. Tripathi, J.S. Rawat, P. Jha, Amendment in sensing response of single walled carbon nanotube (SWCNT) towards ammonia gas with copper phthalocyanine functionalization. Mater. Today: Proc. 28, 1759–1763 (2020)

    CAS  Google Scholar 

  53. Z.L. Qi, Y.H. Cheng, Z. Xu, M.L. Chen, Recent advances in porphyrin-based materials for metal ions detection. Int. J. Mol. Sci. 21(5839), 1–27 (2020)

    Google Scholar 

  54. R. Ridhi, I. Gawri, S.J. Abbas, G.S.S. Saini, S.K. Tripathi, Chemical sensing of copper phthalocyanine sol-gel glass through organic vapors. AIP. Conf. Proc. 1661, 110015 (2015). https://doi.org/10.1063/1.4915460

    Article  Google Scholar 

  55. S. Singh, G.S.S. Saini, S.K. Tripathi, Sensing of chemical vapors by copper phthalocyanine (CuPc) thin films. J. Optoelectron. Adv. Mater. 10, 185–189 (2008)

    CAS  Google Scholar 

  56. R. Ridhi, G.S.S. Saini, S.K. Tripathi, Comparison of interaction mechanisms of substituted and unsubstituted copper phthalocyanine thin films towards organic vapours. J. Basic Appl. Eng. Res. 5, 111–113 (2018)

    Google Scholar 

  57. J. Xiong, W. Tan, J. Cai, K. Lu, X. Mo, Photoelectrochemical sensor based on nickel phthalocyanine–based metal–organic framework for sensitive detection of curcumin. Int. J. Electrochem. Sci. 17, 1–13 (2022)

    Google Scholar 

  58. J. Ma, H. Fan, Z. Li, Y. Jia, A.K. Yadav, G. Dong, W. Wang, W. Dong, S. Wang, Multi-walled carbon nanotubes/polyaniline on the ethylenediamine modified polyethylene terephthalate fibers for a flexible room temperature ammonia gas sensor with high responses. Sens. Actuators B 334, 129677 (2021)

    Article  CAS  Google Scholar 

  59. D.V. Konarev, M.A. Faraonov, A.V. Kuzmin, S.S. Khasanov, Y. Nakano, S.I. Norko, M.S. Batov, A. Otsuka, H. Yamochi, G. Saito, R.N. Lyubovskaya, Crystalline salts of metal phthalocyanine radical anions [M(Pc3-)] (M = CuII, PbII, VIVO, SnIVCl2) with cryptand(Na+) cations: structure, optical and magnetic properties. New J. Chem. 41, 6866–6874 (2017)

    Article  CAS  Google Scholar 

  60. O. Adegoke, T. Nyokong, Unsymmetrically substituted nickel triazatetra-benzcorrole and phthalocynanine complexes: conjugation to quantum dots and applications as fluorescent “Turn ON” sensors. J. Fluoresc. 24, 481–491 (2014)

    Article  CAS  Google Scholar 

  61. H.Z. Gok, B. Farsak, H. Keles, M. Keles, Novel metal-free and metallophthalocyanines containing four 21-membered pentathiadiaza macrocycles: synthesis, characterization, and study of aggregation properties. Turk. J. Chem. 38, 1073–1082 (2014)

    Article  Google Scholar 

  62. H.P. Karaoglu, A.K. Burat, α- and β-substituted metal-free phthalocyanines: synthesis, photophysical and electrochemical properties. Molecules 25, 363–377 (2020)

    Article  Google Scholar 

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Acknowledgements

Dr. R. Ridhi is thankful to Department of Science and Technology, Inspire for providing the fellowship and SAIF Department, Panjab University Chandigarh for providing necessary facilities and technical support for the work.

Funding

Funding was provided by Department of Science and Technology (DST), New Delhi, India (Grant No. DST Inspire Fellow).

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Authors and Affiliations

  1. Department of Physics, Panjab University, Chandigarh, 160014, India

    R. Ridhi, G. S. S. Saini & S. K. Tripathi

  2. Mehr Chand Mahajan DAV College, Sector-36, Chandigarh, 160036, India

    R. Ridhi

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Contributions

RR: conceptualization, methodology, investigation, formal analysis, writing-original draft preparation. GSSS: conceptualization, validation, writing-review and editing, supervision. SKT: conceptualization, validation, writing-review and editing, supervision.

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Ridhi, R., Saini, G.S.S. & Tripathi, S.K. Influence of metals and substituent on interaction behaviour of metal phthalocyanines combinations with organic vapors. J Mater Sci: Mater Electron 34, 549 (2023). https://doi.org/10.1007/s10854-023-09985-5

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