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Calix[4]Aren Derivative Based Gas Sensor Studies

Year 2023, Volume: 2 Issue: 1, 43 - 51, 21.05.2023

Abstract

The preparation processes of organic thin films to be formed using two different components of C11AMINE and CBAMINE, which are calix[4]arene derivatives, were followed using Langmuir-Blodgett (LB), Quartz Crystal Microbalance (QCM), Atomic Force Microscopy (AFM) and Surface Plasma Resonance. With the LangmuirBlodgett technique, thin films with water-air intermediate properties were produced by using different substrates. In this study, the behavior of two different calyx[4]arene molecules against some organic solvent molecules was investigated by Surface Plasmon Resonance (SPR) technique. In the measurements made with SPR, the calix[4]arene solution was coated with Langmuir Blodgett thin film coating technique and their reactions to chloroform, benzene, toluene and ethyl alcohol molecules in the vapor phase and intermolecular interactions were investigated with the help of a special device. The sensor properties of these thin films against organic volatile compounds were investigated.

References

  • C. D. Gutsche, “Calixarenes,” Royal Society of Chemistry, Cambridge, England, 1989, pp. 210.
  • C. D. Gutsche, “Calixarenes: An Introduction (Monographs in Supramolecular Chemistry),’’ 2nd ed. London, England, RSC Publishing, vol 10, 2008.
  • G. Mc Mahon, R. Wall, K. Nolan, D. Diamond, “Characterisation of the estersubstitued products of the reaction of p-t-butyl calix[4]arene and ethyl bromoacetate using LCUV-MS and LC-DAD,” Talanta, 57 : 1119–1132, July, 2002.
  • C. Rizzoli, G.D. Andreetti, R. Ungaro, A.J. Pochini, “Molecular inclusion in functionalized macrocycles 4.the crystal and molecular structure of the cyclo{tetrakis[(5-t-butyl–2- acetoxy–1,3-phenylene)methylene]}-acetic acid (1:1) clathrate,’’ J. Mol. Struct., 82(1–2), 82–133, 1982.
  • C. D. Gutsche, B. Dhawan, J. A. Levine, K. H. No, L. J. Bauer, ‘’Calixarenes 9: Conformational isomers of the ethers and esters of calix[4]arenes,’’ Tetrahedron, 39 :409–426, 1983.
  • V. Böhmer, ‘’Claixarenes, Macrocycles with (almost) unlimited possibilities,’’ Angew. Chem. Int. Edit., 34:7, 713–745, April, 1995.
  • M. A. Markowız, V. Janout, D. G. Castner, S. L. Regen, ‘’Perforated monolayers design and Synthesis of porous and Cohesive monolayers from Mercurated Calix[n]arenes,’’ J. Am. Chem. Soc., 111 (21), 8192–8200, October, 1989.
  • M. Conner, V. Janout, I. Kudelka, p. Dedek, j. Zhu, S. L., Regen, “Perforated monolayers fabrication of Calix[6]arene-Based composite membranes that function as molecular-sieves,” Langmuir, 9, 2389–2397, September, 1993.
  • P. Vitovič, D. P. Nikolelis, T. Hianik, ‘Study of calix[4]resorcinarene–dopamine complexation in mixed phospholipid monolayers formed at the air–water interface,’’ Biochim. Biophys. Acta, 1758:11, 1852–1861, November, 2006.
  • F. Davıs, C. J. M Stirling, ‘’Calix-4- resorcinarene Monolayers and Multilayers: Formation, Structure, and Differential Adsorption,’’ Langmuir, 12:22, 5365-5374, October, 1996.
  • M.Z. Ildıko´, ‘’Selective complex formation of some chromogenic calix[4]arene derivatives detected by Fourier transform infrared spectroscopy 1. Solution experiments,‘’ Spectrochimica Acta Part A, 59:1, 19-27, January, 2003.
  • S. Kunsági-Máté, G. Nagy, L. Kollár, ‘’Host– guest interaction of kaliksarene moleküls with neutral benzotrifluorides Comparison of luminescence spectral data with results of model calculations relating to complex, formation,‘’ Analytica Chimica Acta, 428:2, 301–307, February, 2001.
  • I. Oueslati, ‘’Calix(aza)crowns: synthesis, recognition, and coordination,’’ Tetrahedron, 63:44, 10840-10851, October, 2007.
  • D. Fılenko, T. Gotszalk, Z. Kazantseva, O. Rabinovych, I. Koshets, Y. Shirshov, V.I. Kalchenko, I. Rangelow, ‘’Chemical gas sensors based on kaliksarene-coated discontinuous gold films,’’ Sensors and Actuators B ,111, 264– 270, November, 2005.
  • Yu.M. Shirshov, S.A. Zynio, E.P. Matsas, G.V. Beketov, A.V. Prokhorovich, E.F. Venger, L.N. Markovskiy, V.I. Kalchenko, A.V. Soloviov, R. Merker, “Optical parameters of thin calixarene films and their response to benzene, toluene and chloroform adsorption”, Supramolecular Science, 4:3-4, 491-494, September – December, 1997.
  • E. K. Ertürün, “Anyon-seçici elektrot hazırlanması: Dikromat-seçici elektrot”, Doktora Tezi, Fen Bilimleri Enstitüsü, Ankara Üniversitesi, Ankara, Türkiye, 2006.
  • Z. Özbek, “Kalikseren maddelerinin ince film ve elektrik özellikleri,” Yüksek Lisans Tezi, Fen Bilimleri Enstitüsü, Balıkesir Üniversitesi, Balıkesir, Türkiye, 2007.
  • I. Pockrand, “Surface plasma oscillations at silver surfaces with thin transparent and absorbing coatings,” Surf. Sci., 72:3, 577-88, April, 1978.
  • Z. Özbek, R. Çapan, H. Göktaş, S. Şen, F. G. İnce, M. E. Özel, F. Davis, “Optical parameters of calix[4]arene films and their response to volatile organic vapors,” Sensors and Actuators B, 158:1, 235–240, November, 2011.
  • A. V. Nabok, T. Richardson, C. McCartney, N. Cowlam, F. Davis, C. J. M. Stirling, A. K. Ray, V. Gacem, A. Gibaud, “Size-quantization in extremely small CdS clusters formed in calixarene LB films”, Thin Solid Films, 327–329, 510–514, August, 1998.
  • A. Nabok, A. K. Ray, Iwantono, A. Hassan and M. Simmonds A. Nabok, A. K. Ray, A. H. Iwantono, M. Simmonds, "Optical study on IIVI semiconductor nanoparticles in LangmuirBlodgett films”, IEEE Trans. Nanotech., 2:1, 44- 49, March, 2003.
  • A.K Hassan, A.V Nabok, A.K Ray, A Lucke, K Smith, C.J.M Stirling, F Davis, “[23] Thin films of calix-4-resorcinarene deposited by spin coating and Langmuir–Blodgett techniques: determination of film parameters by surface plasmon resonance”, Mat. Sci. Eng. C, 8–9, 251– 255, December, 1999.
  • A. V. Nabok, A. K. Hassan, A. K. Ray, “Condensation of organic vapours within nanoporous calixarene thin films”, J. Mater. Chem., 10, 189-194, December, 1999.
  • A.K. Hassan, A.K. Ray, A.V. Nabok, T. Wilkop, “Kinetic studies of BTEX vapour adsorption onto surfaces of calix-4-resorcinarene films”, Appl. Sur. Sci., 182:1-2, 49-54, October, 2001.
  • M. C. Oh, K. J. Kim, J. H. Lee, H. X. Chen, K. N. Koh, “Polymeric waveguide biosensors with calixarene monolayer for detecting potassium ion concentration”, Appl. Phys. Lett., 89:25, 251104, December, 2006.
  • Z.I. Kazantseva, N.V. Lavrik, A.V. Nabok, O.P. Dimitriev, B.A. Nesterenko, V.I. Kalchenko, S.V. Vysotsky, L.N. Markovskiy, A.A. Marchenko, “Structure and electronic properties of Langmuir-Blodgett films of calixarene/fullerene composites”, Supramolecular Sci., 4:3-4, 341-347, December, 1997.
  • R. Çapan, T. H. Richardson, “Pyroelectric effect in a mixed polysiloxane/eicosylamine Langmuir-Blodgett Thin Film,” Materials Letters, vol. 25, pp. 3131-3135, 2004.
  • D. Lacey, T. Richardson, F. Davis, and R. Capan, “Pyroelectric Superlattices Based on Polysiloxane / Calix[n]arene Alternate LB Films,” Materials Science & Engineering C, vol. 8-9 pp. 377-384, 1999.
  • R. Çapan, “Pyroelectric and Dielectric Characterisation of Alternate Layer LangmuirBlodgett Films Incorporating Ions,” Materials Letters, vol. 61, no. 4-5, pp. 1231-1234, 2007.
  • R. Çapan, T. H. Richardson, D. Lacey, “Pyroelectric Effect in Langmuir-Blodgett Films Incorporating Ions,” Thin Solid Films, vol. 468, no. 1-2, pp. 262-267, 2004.
  • R. Capan, T. Richardson, D. Lacey, “Cd 2+ and Mn 2+ Incorporation in Copolysiloxane/Eicosylamine Alternate Layer LB Films:Influence on Pyroelectric Activity,” Thin Solid Films, vol: 327-329, pp. 369-372, 1998.

Kaliks[4]Aren Türevi Temelli Gaz Sensör Çalışmaları

Year 2023, Volume: 2 Issue: 1, 43 - 51, 21.05.2023

Abstract

Kaliks[4]aren türevi olan iki farklı C11AMINE ve CBAMINE maddeleri kullanılarak oluşturulacak organik ince filmlerin hazırlanma süreçleri, Langmuir-Blodgett (LB), Kuartz Kristal Mikrobalans (QCM), Atomik Kuvvet Mikroskopi (AFM) ve Yüzey Plazma Rezonansı teknikleri ile takip edilmiştir. Langmuir-Blodgett tekniği ile farklı alttaşlar kullanılarak su-hava ara yüzeyinde ince filmlerin üretimi gerçekleştirilmiştir. Bu çalışmada, iki farklı kaliks[4]aren moleküllerinin bazı organik çözücü moleküllerine karşı davranışları Yüzey Plazmon Rezonans (SPR) tekniği ile incelenmiştir. SPR ile yapılan ölçümlerde kaliks[4]aren çözeltisi ile Langmuir-Blodgett ince film kaplama tekniği ile kaplanmış ve özel bir düzenek yardımı ile buhar fazındaki kloform, benzen, toluen ve etil alkol moleküllerine karşı tepkileri ve moleküler arası etkileşimler incelenmiştir. Bu ince filmlerin, organik uçucu bileşiklere karşı olan sensör özellikleri incelenmiştir.

References

  • C. D. Gutsche, “Calixarenes,” Royal Society of Chemistry, Cambridge, England, 1989, pp. 210.
  • C. D. Gutsche, “Calixarenes: An Introduction (Monographs in Supramolecular Chemistry),’’ 2nd ed. London, England, RSC Publishing, vol 10, 2008.
  • G. Mc Mahon, R. Wall, K. Nolan, D. Diamond, “Characterisation of the estersubstitued products of the reaction of p-t-butyl calix[4]arene and ethyl bromoacetate using LCUV-MS and LC-DAD,” Talanta, 57 : 1119–1132, July, 2002.
  • C. Rizzoli, G.D. Andreetti, R. Ungaro, A.J. Pochini, “Molecular inclusion in functionalized macrocycles 4.the crystal and molecular structure of the cyclo{tetrakis[(5-t-butyl–2- acetoxy–1,3-phenylene)methylene]}-acetic acid (1:1) clathrate,’’ J. Mol. Struct., 82(1–2), 82–133, 1982.
  • C. D. Gutsche, B. Dhawan, J. A. Levine, K. H. No, L. J. Bauer, ‘’Calixarenes 9: Conformational isomers of the ethers and esters of calix[4]arenes,’’ Tetrahedron, 39 :409–426, 1983.
  • V. Böhmer, ‘’Claixarenes, Macrocycles with (almost) unlimited possibilities,’’ Angew. Chem. Int. Edit., 34:7, 713–745, April, 1995.
  • M. A. Markowız, V. Janout, D. G. Castner, S. L. Regen, ‘’Perforated monolayers design and Synthesis of porous and Cohesive monolayers from Mercurated Calix[n]arenes,’’ J. Am. Chem. Soc., 111 (21), 8192–8200, October, 1989.
  • M. Conner, V. Janout, I. Kudelka, p. Dedek, j. Zhu, S. L., Regen, “Perforated monolayers fabrication of Calix[6]arene-Based composite membranes that function as molecular-sieves,” Langmuir, 9, 2389–2397, September, 1993.
  • P. Vitovič, D. P. Nikolelis, T. Hianik, ‘Study of calix[4]resorcinarene–dopamine complexation in mixed phospholipid monolayers formed at the air–water interface,’’ Biochim. Biophys. Acta, 1758:11, 1852–1861, November, 2006.
  • F. Davıs, C. J. M Stirling, ‘’Calix-4- resorcinarene Monolayers and Multilayers: Formation, Structure, and Differential Adsorption,’’ Langmuir, 12:22, 5365-5374, October, 1996.
  • M.Z. Ildıko´, ‘’Selective complex formation of some chromogenic calix[4]arene derivatives detected by Fourier transform infrared spectroscopy 1. Solution experiments,‘’ Spectrochimica Acta Part A, 59:1, 19-27, January, 2003.
  • S. Kunsági-Máté, G. Nagy, L. Kollár, ‘’Host– guest interaction of kaliksarene moleküls with neutral benzotrifluorides Comparison of luminescence spectral data with results of model calculations relating to complex, formation,‘’ Analytica Chimica Acta, 428:2, 301–307, February, 2001.
  • I. Oueslati, ‘’Calix(aza)crowns: synthesis, recognition, and coordination,’’ Tetrahedron, 63:44, 10840-10851, October, 2007.
  • D. Fılenko, T. Gotszalk, Z. Kazantseva, O. Rabinovych, I. Koshets, Y. Shirshov, V.I. Kalchenko, I. Rangelow, ‘’Chemical gas sensors based on kaliksarene-coated discontinuous gold films,’’ Sensors and Actuators B ,111, 264– 270, November, 2005.
  • Yu.M. Shirshov, S.A. Zynio, E.P. Matsas, G.V. Beketov, A.V. Prokhorovich, E.F. Venger, L.N. Markovskiy, V.I. Kalchenko, A.V. Soloviov, R. Merker, “Optical parameters of thin calixarene films and their response to benzene, toluene and chloroform adsorption”, Supramolecular Science, 4:3-4, 491-494, September – December, 1997.
  • E. K. Ertürün, “Anyon-seçici elektrot hazırlanması: Dikromat-seçici elektrot”, Doktora Tezi, Fen Bilimleri Enstitüsü, Ankara Üniversitesi, Ankara, Türkiye, 2006.
  • Z. Özbek, “Kalikseren maddelerinin ince film ve elektrik özellikleri,” Yüksek Lisans Tezi, Fen Bilimleri Enstitüsü, Balıkesir Üniversitesi, Balıkesir, Türkiye, 2007.
  • I. Pockrand, “Surface plasma oscillations at silver surfaces with thin transparent and absorbing coatings,” Surf. Sci., 72:3, 577-88, April, 1978.
  • Z. Özbek, R. Çapan, H. Göktaş, S. Şen, F. G. İnce, M. E. Özel, F. Davis, “Optical parameters of calix[4]arene films and their response to volatile organic vapors,” Sensors and Actuators B, 158:1, 235–240, November, 2011.
  • A. V. Nabok, T. Richardson, C. McCartney, N. Cowlam, F. Davis, C. J. M. Stirling, A. K. Ray, V. Gacem, A. Gibaud, “Size-quantization in extremely small CdS clusters formed in calixarene LB films”, Thin Solid Films, 327–329, 510–514, August, 1998.
  • A. Nabok, A. K. Ray, Iwantono, A. Hassan and M. Simmonds A. Nabok, A. K. Ray, A. H. Iwantono, M. Simmonds, "Optical study on IIVI semiconductor nanoparticles in LangmuirBlodgett films”, IEEE Trans. Nanotech., 2:1, 44- 49, March, 2003.
  • A.K Hassan, A.V Nabok, A.K Ray, A Lucke, K Smith, C.J.M Stirling, F Davis, “[23] Thin films of calix-4-resorcinarene deposited by spin coating and Langmuir–Blodgett techniques: determination of film parameters by surface plasmon resonance”, Mat. Sci. Eng. C, 8–9, 251– 255, December, 1999.
  • A. V. Nabok, A. K. Hassan, A. K. Ray, “Condensation of organic vapours within nanoporous calixarene thin films”, J. Mater. Chem., 10, 189-194, December, 1999.
  • A.K. Hassan, A.K. Ray, A.V. Nabok, T. Wilkop, “Kinetic studies of BTEX vapour adsorption onto surfaces of calix-4-resorcinarene films”, Appl. Sur. Sci., 182:1-2, 49-54, October, 2001.
  • M. C. Oh, K. J. Kim, J. H. Lee, H. X. Chen, K. N. Koh, “Polymeric waveguide biosensors with calixarene monolayer for detecting potassium ion concentration”, Appl. Phys. Lett., 89:25, 251104, December, 2006.
  • Z.I. Kazantseva, N.V. Lavrik, A.V. Nabok, O.P. Dimitriev, B.A. Nesterenko, V.I. Kalchenko, S.V. Vysotsky, L.N. Markovskiy, A.A. Marchenko, “Structure and electronic properties of Langmuir-Blodgett films of calixarene/fullerene composites”, Supramolecular Sci., 4:3-4, 341-347, December, 1997.
  • R. Çapan, T. H. Richardson, “Pyroelectric effect in a mixed polysiloxane/eicosylamine Langmuir-Blodgett Thin Film,” Materials Letters, vol. 25, pp. 3131-3135, 2004.
  • D. Lacey, T. Richardson, F. Davis, and R. Capan, “Pyroelectric Superlattices Based on Polysiloxane / Calix[n]arene Alternate LB Films,” Materials Science & Engineering C, vol. 8-9 pp. 377-384, 1999.
  • R. Çapan, “Pyroelectric and Dielectric Characterisation of Alternate Layer LangmuirBlodgett Films Incorporating Ions,” Materials Letters, vol. 61, no. 4-5, pp. 1231-1234, 2007.
  • R. Çapan, T. H. Richardson, D. Lacey, “Pyroelectric Effect in Langmuir-Blodgett Films Incorporating Ions,” Thin Solid Films, vol. 468, no. 1-2, pp. 262-267, 2004.
  • R. Capan, T. Richardson, D. Lacey, “Cd 2+ and Mn 2+ Incorporation in Copolysiloxane/Eicosylamine Alternate Layer LB Films:Influence on Pyroelectric Activity,” Thin Solid Films, vol: 327-329, pp. 369-372, 1998.
There are 31 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Research Articles
Authors

Zikriye Özbek 0000-0002-9112-1478

Publication Date May 21, 2023
Published in Issue Year 2023 Volume: 2 Issue: 1

Cite

APA Özbek, Z. (2023). Kaliks[4]Aren Türevi Temelli Gaz Sensör Çalışmaları. Türk Mühendislik Araştırma Ve Eğitimi Dergisi, 2(1), 43-51.
AMA Özbek Z. Kaliks[4]Aren Türevi Temelli Gaz Sensör Çalışmaları. TMAED. May 2023;2(1):43-51.
Chicago Özbek, Zikriye. “Kaliks[4]Aren Türevi Temelli Gaz Sensör Çalışmaları”. Türk Mühendislik Araştırma Ve Eğitimi Dergisi 2, no. 1 (May 2023): 43-51.
EndNote Özbek Z (May 1, 2023) Kaliks[4]Aren Türevi Temelli Gaz Sensör Çalışmaları. Türk Mühendislik Araştırma ve Eğitimi Dergisi 2 1 43–51.
IEEE Z. Özbek, “Kaliks[4]Aren Türevi Temelli Gaz Sensör Çalışmaları”, TMAED, vol. 2, no. 1, pp. 43–51, 2023.
ISNAD Özbek, Zikriye. “Kaliks[4]Aren Türevi Temelli Gaz Sensör Çalışmaları”. Türk Mühendislik Araştırma ve Eğitimi Dergisi 2/1 (May 2023), 43-51.
JAMA Özbek Z. Kaliks[4]Aren Türevi Temelli Gaz Sensör Çalışmaları. TMAED. 2023;2:43–51.
MLA Özbek, Zikriye. “Kaliks[4]Aren Türevi Temelli Gaz Sensör Çalışmaları”. Türk Mühendislik Araştırma Ve Eğitimi Dergisi, vol. 2, no. 1, 2023, pp. 43-51.
Vancouver Özbek Z. Kaliks[4]Aren Türevi Temelli Gaz Sensör Çalışmaları. TMAED. 2023;2(1):43-51.