QCM sensors coated with calixarenes bearing sensitive chiral moieties for chiral discrimination of 1-phenylethylamine enantiomers
- 95 Downloads
This article describes the enantiomeric discrimination properties of new chiral calixarene derivatives bearing (S)-/(R)-1-phenylethylamine moieties (5a and 5b, respectively) towards the 1-phenylethylamine enantiomers on QCM surface. Initial experiments demonstrated that the 5b coated QCM sensor was the most effective sensing material for enantiomeric discrimination of (R)-/(S)-1-phenylethylamine by exhibiting much more sensing ability towards (R)-enantiomer than (S)-enantiomer. Sensitivity, detection limit and time constant of the 5b coated QCM sensor has been were calculated as 0.082 Hz/µM, 2.7 µM, and 319.2 s, respectively. Additionally, effects of calixarene content and different coating technique on enantiomeric discrimination, and Langmuir and Freundlich isotherms of the sensing results also were studied. As a result, it has been demonstrated that the coating of QCM sensor with a chiral calixarene (5b) having (S)-1-phenylethylamine moieties provides substantially enantiomeric discrimination of 1-phenylethylamine enantiomers.
Keywords1-Phenylethylamine Organic coatings Calixarene Enantiomeric discrimination Quartz crystal microbalance sensor
We thank the Technical Research Council of Turkey (TUBITAK—Grant No. 115Z249) and the Research Foundation of the Selçuk University (SUBAP-Grant No. 16401003), Konya, Turkey and for financial support of this work produced from Egemen Ozcelik’s M.Sc. Thesis.
- 8.Mishra, S.K., Chaudhari, S.R., Lakshmipriya, A., Pal, I., Lokesh, N., Suryaprakash, N.: Novel synthetic as well as natural auxiliaries with a blend of NMR methodological developments for chiral analysis in isotropic media. In Annual Reports on NMR Spectroscopy, Vol. 91, pp. 143–292. Academic Press, Cambridge (2017)Google Scholar
- 10.Kertész, J., Huszthy, P., Kormos, A., Bertha, F., Horváth, V., Horvai, G.: Synthesis of new optically active acridino-18-crown-6 ligands and studies of their potentiometric selectivity toward the enantiomers of protonated 1-phenylethylamine and metal ions. Tetrahedron 20(24), 2795–2801 (2009)CrossRefGoogle Scholar
- 11.Wang, L., Zhang, Y., Wu, A., Wei, G.: Designed graphene-peptide nanocomposites for biosensor applications: a review. Anal. Chim. Acta 985, 24–40 (2017)Google Scholar
- 16.Jearanaikoon, P., Prakrankamanant, P., Leelayuwat, C., Wanram, S., Limpaiboon, T., Promptmas, C.: The evaluation of loop-mediated isothermal amplification-quartz crystal microbalance (LAMP-QCM) biosensor as a real-time measurement of HPV16 DNA. J. Virol. Methods 229, 8–11 (2016)CrossRefGoogle Scholar
- 23.Juaristi, E., León-Romo, J.L., Reyes, A., Escalante, J.: Recent applications of α-phenylethylamine (α-PEA) in the preparation of enantiopure compounds. Part 3: α-PEA as chiral auxiliary. Part 4: α-PEA as chiral reagent in the stereodifferentiation of prochiral substrates. Tetrahedron 10(13), 2441–2495 (1999)CrossRefGoogle Scholar
- 27.Long, G.L., Winefordner, J.D.: Limit of detection a closer look at the IUPAC definition. Anal. Chem. 55(07), 712A–724A (1983)Google Scholar
- 34.Grate, J.W., Snow, A., Ballantine, D.S., Wohltjen, H., Abraham, M.H., McGill, R.A., Sasson, P.: Determination of partition coefficients from surface acoustic wave vapor sensor responses and correlation with gas-liquid chromatographic partition coefficients. Anal. Chem. 60(9), 869–875 (1988)CrossRefGoogle Scholar
- 41.Weber, W.J.: Physicochemical Processes for Water Quality Control. Wiley, New York (1972)Google Scholar