Host-Guest Sensing Interactions of Calixarene-Entrapped Para-Aminobenzoic Acid Using the Langmuir Technique


  • Yeong Yi Wong Department of Physics, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900, Tanjong Malim, Perak, Malaysia
  • Faridah Lisa Supian Department of Physics, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900, Tanjong Malim, Perak, Malaysia
  • Nur Farah Nadia Abd Karim Department of Physics, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900, Tanjong Malim, Perak, Malaysia
  • Mazlina Musa Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900, Tanjong Malim, Perak, Malaysia
  • Mohd Syahriman Mohd Azmi Department of Physics, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900, Tanjong Malim, Perak, Malaysia
  • Ratnawulan Department of Physics, Faculty of Mathematics and Natural Sciences, Universitas Negeri Padang, 25171, Kota Padang, Sumatera Barat, Indonesia



Calixarenes, drug sensor, host-guest, isotherm, Langmuir, PABA


Calixarenes are frequently studied as the host supramolecule in drug carrier applications. The ability to encapsulate and control drug delivery is due to their unique structures with a hydrophobic upper rim and a hydrophilic lower rim. Para-aminobenzoic acid (PABA) is a drug used as the main ingredient in sunscreen products with photoallergic contact dermatitis effects. This study has been motivated by the necessity of developing a PABA sensor even at a deficient concentration. In this work, the uses of two calixarenes, calix[4]arene (C4) and calix[6]arene (C6), in entrapping the PABA drug have been studied using the Langmuir technique. In the Langmuir-Blodgett trough, calixarenes in solution form were prepared and spread on the subphase to form the Langmuir monolayer. The formation of Langmuir films by C4 and C6 has been investigated based on the surface pressure-area ( - ) isotherm and surface potential-area ( - ) isotherm recorded using Langmuir apparatus KSV 2000 System 2. The differences and changes of the isotherms with the presence of para-aminobenzoic acid (PABA) in the subphase during the formation of Langmuir films have been observed and studied. The interactions between calixarenes and PABA have been shown by the effective dipole moment ( ) of the calixarene-PABA complexes calculated based on the  results using the Helmholtz equation. Host-guest interaction shown by the sensing of PABA by calixarenes happens most probably at the lower rim of calixarenes due to the amphiphilic property of calixarenes. The findings of this study can be applied to the potential application of drug sensors using C4 and C6.


Download data is not yet available.


Al-Alwani AJ, Mironyuk VN, Pozharov MV, Gavrikov MV, Glukhovskoy EG. (2022). Formation and phase behavior of porphyrin/arachidic acid mixed systems and morphology study of Langmuir-Schaefer thin films. Soft Materials, 20(3), 310-321.

Azahari NA, Supian FL, Richardson TH, Malik SA. (2014). Properties of calix4-lead (Pb) films using Langmuir-Blodgett (LB) technique as an application of ion sensor. Advanced Materials Research, 895, 8-11.

Baklouti L. (2007). Calixarenes in the Nanoworld. Springer, Dordrecht.

Becher J, Schaumburg K. (2013). Molecular engineering for advanced materials. Springer Science & Business Media, Berlin.

Bland HC, Moilanen JA, Ekholm FS, Paananen RO. (2019). Investigating the role of specific tear film lipids connected to dry eye syndrome: A study on O-Acyl-ω-hydroxy fatty acids and diesters. Langmuir, 35(9), 3545-3552.

Chachaj-Brekiesz A, Kobierski J, Wnętrzak A, Dynarowicz-Latka P. (2021). Electrical properties of membrane phospholipids in Langmuir monolayers. Membranes, 11(1), 53.

da Rocha Rodrigues R, da Silva RLCG, Caseli L, Peres LO. (2020). Conjugated polymers as Langmuir and Langmuir-Blodgett films: Challenges and applications in nanostructured devices. Advances in Colloid and Interface Science, 285, 102277.

da Silva RLCG, Sharma SK, Paudyal S, Mintz KJ, Caseli L, Leblanc RM. (2020). Surface chemistry and spectroscopic studies of the native phenylalanine dehydrogenase Langmuir monolayer at the air/aqueous NaCl interface. Journal of Colloid and Interface Science, 560, 458-466.

De Leener G, Over D, Reinaud O, Jabin I. (2022). Turning on anion and betaine hosting by a small structural change of a biomimetic cavity: A case study. Supramolecular Chemistry, 33(7), 370-379.

DeLeo V A. (2018). Photoallergy. Routledge, Oxfordshire.

Drozd KV, Arkhipov SG, Boldyreva EV, Perlovich GL. (2018). Crystal structure of a 1: 1 salt of 4-aminobenzoic acid (vitamin B10) with pyrazinoic acid. Acta Crystallographica Section E: Crystallographic Communications, 74(12), 1923-1927.

Dynarowicz-Łątka P, Kita K, Milart P, Dhanabalan A, Cavalli A, da Silva Filho DA, dos Santos d MC, Oliveira Jr ON. (2002). Influence of apolar group structure on the properties of Langmuir monolayers of polyphenyl carboxylic acids. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 198, 141-150.

Español ES, Villamil MM. (2019). Calixarenes: Generalities and their role in improving the solubility, biocompatibility, stability, bioavailability, detection, and transport of biomolecules. Biomolecules, 9(3), 90.

Fahmy SA, Ponte F, Abd El-Rahman MK, Russo N, Sicilia E, Shoeib T. (2018). Investigation of the host-guest complexation between 4-sulfocalix[4]arene and nedaplatin for potential use in drug delivery. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 193, 528-536.

Gontero D, Lessard-Viger M, Brouard D, Bracamonte AG, Boudreau D, Veglia AV. (2017). Smart multifunctional nanoparticles design as sensors and drug delivery systems based on supramolecular chemistry. Microchemical Journal, 130, 316-328.

Hidalgo AA, Caetano W, Tabak M, Oliveira Jr ON. (2004). Interaction of two phenothiazine derivatives with phospholipid monolayers. Biophysical chemistry, 109(1), 85-104.

Hua Y, Angle CW. (2013). Brewster angle microscopy of Langmuir films of athabasca bitumens, n-C5 asphaltenes, and SAGD bitumen during pressure-area hysteresis. Langmuir, 29(1), 244-263.

Jurak M, Szafran K, Cea P, Martín S. (2021). Analysis of molecular interactions between components in phospholipid-immunosuppressant-antioxidant mixed Langmuir films. Langmuir, 37(18), 5601-5616.

Kumar S, Chawla S, Zou MC. (2017). Calixarenes based materials for gas sensing applications: A review. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 88(3), 129-158.

Kurniawan YS, Sathuluri RR, Ohto K. (2020). Droplet microfluidic device for rapid and efficient metal separation using host-guest chemistry. Advances in Microfluidic Technologies for Energy and Environmental Applications, 3, 1-19.

Lim DC, Supian FL, Hamzah Y. (2020). Langmuir, Raman, and electrical properties comparison of calixarene and calixarene-rGO using Langmuir Blodgett (LB) technique. Journal of Materials Science: Materials in Electronics, 31(21), 18487-18494.

Liu Z, Dai X, Sun Y, Liu Y. (2020). Organic supramolecular aggregates based on water‐soluble cyclodextrins and calixarenes. Aggregate, 1(1), 31-44.

McMahon G, O’Malley S, Nolan K, Diamond D. (2003). Important calixarene derivatives-their synthesis and applications. Arkivoc, 7, 23-31.

Mirzaei M, Khayat M, Saeidi A. (2012). Determination of para-aminobenzoic acid (PABA) in B-complex tablets using the Multivariate Curve Resolution-Alternating Least Squares (MCR-ALS) method. Scientia Iranica, 19(3), 561-564.

Pellegrini F. (2011). CliffsQuickReview Organic Chemistry II. Houghton Mifflin Harcourt, Boston.

Priyangga KTA, Kurniawan YS, Ohto K, Jumina J. (2022). A review on calixarene fluorescent chemosensor agents for various analytes. Journal of Multidisciplinary Applied Natural Science, 2(1), 23-40.

Razali AS, Supian FL, Al Naim AF, Ayop SK, Azahari NA. (2021). Raman, FTIR, UV-Visible and FESEM studies on calix [8] arene embedded multi-walled carbon nanotubes nanocomposites using spin coating technique. Journal of Science and Mathematics Letters, 9(2), 1-8.

Ruwoldt J. (2020). A critical review of the physicochemical properties of lignosulfonates: Chemical structure and behavior in aqueous solution, at surfaces and interfaces. Surfaces, 3(4), 622-648.

Sanku RK, Karakus OO, Ilies M, Ilies MA. (2019). Inclusion complexes in drug delivery and drug targeting: Formation, characterization, and biological applications. American Chemical Society, Washington.

Shah A. (2020). A novel electrochemical nanosensor for the simultaneous sensing of two toxic food dyes. ACS Omega, 5(11), 6187-6193.

Singh A, Čížková M, Bišová K, Vítová M. (2021). Exploring mycosporine-like amino acids (MAAs) as safe and natural protective agents against UV-induced skin damage. Antioxidants, 10(5), 683.

Singh RS. (2022). Langmuir and Langmuir-Blodgett films of aromatic amphiphiles. Soft Materials, 20(1), 57-98.

Supian FL, Azahari NA, Juahir Y, Abd Karim NFN, Naim AF. (2021). Correlation of Langmuir isotherm, optical, surface potential and morphological characterizations of two functionalized dihydroxycalix[4]arene for lead cation entrapment. Malaysian Journal of Microscopy, 17(2), 9-19.

Supian FL, Richardson TH, Deasy M, Kelleher F, Ward JP, McKee V. (2010). Interaction between Langmuir and Langmuir-Blodgett films of two calix[4]arenes with aqueous copper and lithium ions. Langmuir, 26(13), 10906-10912.

Troian-Gautier L, Mattiuzzi A, Reinaud O, Lagrost C, Jabin I. (2020). Use of calixarenes bearing diazonium groups for the development of robust monolayers with unique tailored properties. Organic & Biomolecular Chemistry, 18(19), 3624-3637.

Wagner BD. (2020). Host-guest chemistry. De Gruyter, Berlin.

Wang J, Zhu H. (2021). Interaction between polyene antifungal drug and saturated phospholipid monolayer regulated by calcium ions at the air-water interface. Colloids and Surfaces B: Biointerfaces, 207, 111998.

Wong YY, Supian FL, Musa M, Abd Karim NFN, Naim AF. (2022). Calixarenes as host molecules for drug carriers in the cosmetic and medical field. Macromolecular Research, 30(12), 853-862.

Yang SF, Zhang X, Chen PL, Liu ZT, Tian JW, Zhang GX, Zhang DQ. (2017). Diketopyrrolopyrrole‐based semiconducting polymer with both hydrophobic alkyl and hydrophilic tetraethylene glycol chains for monolayer transistor and sensing application. Advanced Electronic Materials, 3(11), 1700120.




How to Cite

Wong , Y. Y., Supian, F. L., Abd Karim, N. F. N., Musa, M., Mohd Azmi, M. S., & Ratnawulan. (2023). Host-Guest Sensing Interactions of Calixarene-Entrapped Para-Aminobenzoic Acid Using the Langmuir Technique. Journal of Science and Mathematics Letters, 11, 63–72.




Most read articles by the same author(s)