Malaysian Journal of Analytical Sciences Vol 21 No 6 (2017): 1342 - 1351

FLUORESCENCE QUENCHING ON MESOPOROUS CARBON NITRIDE BY PHENOL AND ANILINE

(Pelindapan Pendarfluor pada Karbon Nitrida Mesoliang oleh Fenol dan Anilina)

Leny Yuliati^1,2,3*, Ahmad Hanami Abd Kadir⁴, Siew Ling Lee^3,4, Hendrik O. Lintang^1,2,3

¹Ma Chung Research Center for Photosynthetic Pigments

²Department of Chemistry, Faculty of Science and Technology

Universitas Ma Chung, Villa Puncak Tidar N-01, Malang 65151, East Java, Indonesia

³Centre for Sustainable Nanomaterials, Ibnu Sina Institute for Scientific and Industrial Research

⁴Department of Chemistry, Faculty of Science

Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

*Corresponding author: leny.yuliati@machung.ac.id

Received: 7 November 2016; Accepted: 18 September 2017

Abstract

In this study, fluorescence quenching on mesoporous carbon nitride (MCN) was examined in the presence of phenol and aniline. The MCN was synthesized by thermal polymerization of cyanamide using nanocolloidal silica (7 nm) as a hard template and characterized by X-ray diffractometer (XRD), Fourier transform infrared (FTIR), transmission electron microscope (TEM), specific surface area, pore size distribution, and fluorescence spectrophotometer. The MCN showed two excitation wavelengths at 275 and 370 nm, owing to the presence of N=C and N-C terminal groups, respectively. These two excitation wavelengths gave only one emission peak at around 460 nm. Either in the presence of phenol or aniline, the emission intensity of the MCN was confirmed to be quenched in a linear function towards the concentration of phenol or aniline as the quencher molecule. N-C terminal groups were found to have slightly better interactions to phenol and aniline as compared to the N=C groups. Since the emission intensity of MCN was more quenched by phenol molecules than the aniline, it was proposed that the MCN would have stronger interaction to phenol than aniline. This result was also supported by the adsorption data, in which the MCN gave higher adsorption towards phenol than the aniline.

Keywords: mesoporous carbon nitride, phenol, aniline, fluorescence quenching, adsorption

Abstrak

Dalam kajian ini, pelindapan pendarfluor pada karbon nitrida mesoliang (MCN) telah diperiksa dengan kehadiran fenol dan anilina. MCN telah disintesis secara pempolimeran haba sianamida menggunakan silika nanokoloid (7 nm) sebagai templat keras dan telah dicirikan dengan pembelauan sinar-X (XRD), inframerah transformasi Fourier (FTIR), mikroskop elektron transmisi (TEM), luas permukaan, taburan saiz liang, dan spektroskopi pendafluor. MCN menunjukkan dua panjang gelombang pengujaan pada 275 dan 370 nm oleh kerana kehadiran masing – masing N=C dan N-C sebagai kumpulan terminal. Kedua-dua panjang gelombang pengujaan memberikan hanya satu puncak pelepasan pada kira-kira 460 nm.Sama ada dengan kehadiran fenol atau anilina, keamatan pemancaran daripada MCN disahkan mengalami pelindapan dalam fungsi linear terhadap kepekatan fenol atau anilina sebagai molekul pelindap. Kumpulan terminal N-C didapati mempunyai interaksi lebih baik sedikit untuk fenol dan anilina berbanding dengan kumpulan N=C. Oleh kerana keamatan pemancaran MCN didapati lebih terlindap oleh molekul fenol berbanding dengan anilina, adalah dicadangkan bahawa MCN berinteraksi lebih kuat dengan fenol dibandingkan dengan anilina. Keputusan ini juga disokong oleh data penjerapan, dengan MCN memberikan penjerapan yang lebih tinggi terhadap fenol dibandingkan dengan anilina.

Kata kunci: karbon nitrida mesoliang, fenol, anilina, pelindapan pendarfluor, penjerapan

References

1. Vinu, A. (2008). Two-dimensional hexagonally-ordered mesoporous carbon nitrides with tunable pore diameter, surface area and nitrogen content. Advanced Functional Materials, 18(5): 816 – 827.

2. Teter, D. M. and Hemley R. J. (1996). Low-compressibility carbon nitride. Science, 271(5245): 53 – 55.

3. Corkill, J. L. and Cohen, M. L. (1993). Calculated quasiparticle band gap of β-C₃N₄. Physical Review B, 48(23): 17622 – 17624.

4. Goettmann, F., Fischer, A., Antonietti, M. and Thomas, A. (2006). Chemical synthesis of mesoporous carbon nitrides using hard templates and their use as a metal-free catalyst for Friedel-Craft reaction of benzene. Angewandte Chemie International Edition, 45(27): 4467 – 4471.

5. Gillan, E. G. (2000). Synthesis of nitrogen-rich carbon nitride networks from an energetic molecular azide precursor. Chemistry of Materials, 12(12): 3906 – 3912.

6. Komatsu, T. (2001). Attempted chemical synthesis of graphite-like carbon nitride. Journal of Materials Chemistry, 11: 799 – 801.

7. Sam, M. S., Lintang, H. O., Sanagi, M. M., Lee, S. L. and Yuliati, L. (2014). Mesoporous carbon nitride for adsorption and fluorescence sensor of N-nitrosopyrrolidine. Spectrochimica Acta Part A: Molecular and Bio-molecular Spectroscopy, 124: 357 – 364.

8. Sam, M. S., Lintang, H. O., Sanagi, M. M., Lee, S. L. and Yuliati, L. (2014). Adsorption of aniline using novel mesoporous carbon nitride. Advanced Materials Research, 95: 135–139.

9. Sam, M. S., Tiong, P., Lintang, H. O., Sanagi, M. M., Lee, S. L. and Yuliati, L. (2015). Mesoporous carbon nitride as a metal-free catalyst for the removal of aniline. RSC Advances, 5: 44578 – 44586.

10. Lee, S.C., Lintang, H.O. and Yuliati, L. (2012). A urea precursor to synthesize carbon nitride with mesoporosity for enhanced activity in the photocatalytic removal of phenol. Chemistry An Asian Journal, 7(9): 2139 – 2144.

11. Cui, Y., Zhang, J., Zhang, G., Huang, J., Liu, P., Antonietti, M. and Wang X. (2011). Synthesis of bulk and nanoporous carbon nitride polymers from ammonium thiocyanate for photocatalytic hydrogen evolution. Journal of Materials Chemistry, 21: 13032 – 13039.

12. Wang, X., Maeda, K., Chen, X., Takanabe, K., Domen, K., Hou, Y., Fu, X. and Antonietti, M. (2009). Polymer semiconductors for artificial photosynthesis: hydrogen evolution by mesoporous graphitic carbon nitride with visible light. Journal of the American Chemical Society, 131(5): 1680 – 1681.

13. Wang, Y., Wang, X. and Antonietti, M. (2012). Polymeric graphitic carbon nitrides as a heterogeneous organo-catalyst: from photochemistry to multipurpose catalysis to sustainable chemistry. Angewandte Chemie Inter-national Edition, 51(1): 68 – 89.

14. Thomas, A., Fischer, A., Goettmann, F., Antonietti, M., Müller, J.-O., Schlögl, R. and Carlsson, J. M. (2008). Graphitic carbon nitride materials: Variation of structure and morphology and their use as metal-free catalyst. Journal of Materials Chemistry, 18(41): 4893 – 4908.

15. Zhang, Y., Mori, T. and Ye, J. (2012). Polymeric carbon nitrides: Semiconducting properties and emerging applications in photocatalysis and photoelectrochemical energy conversion. Science of Advanced Materials, 4(2): 282 – 291.

16. Lee, E. Z., Jun, Y. S., Hong, W. H., Thomas, A. and Jin, M. M. (2010). Cubic mesoporous graphitic carbon(IV) nitride: an all-in-one chemosensor for selective optical sensing of metal ions. Angewandte Chemie International Edition, 49 (50): 9706 – 9710.

17. Lee, E. Z., Lee, S. U., Heo, N. S., Stucky, G. D., Jun, Y. S. and Hong, W. H. (2012). A fluorescent sensor for selective detection of cyanide using mesoporous graphitic carbon(IV) nitride. Chemical Communications, 48(33): 3942 – 3944.

18. Tian, J., Liu, Q., Asiri, A. M., Al Youbi, A. O. and Sun, X. (2013). Ultrathin graphitic carbon nitride nanosheet: a highly efficient fluorosensor for rapid, ultrasensitive detection of Cu²⁺. Analytical Chemistry, 85(11): 5595 – 5599.

19. Alim, N. S., Lintang, H. O. and Yuliati, L. (2015). Fabricated metal-free carbon nitride characterizations for fluorescence chemical sensor of nitrate ions. Jurnal Teknologi, 76(13): 1 – 6.

20. Dąbrowski, A., Podkościelny, P., Hubicki, Z. and Barczak, M. (2005). Adsorption of phenolic compounds by activated carbon - A critical review. Chemosphere, 58(8): 1049 – 1070.

21. Busca, G., Berardinelli, S., Resini, C. and Arrighi, L. (2008). Technologies for the removal of phenol from fluid streams: A short review of recent developments. Journal of Hazardous Materials, 160(2-3): 265 – 288.

22. Ahmed, S., Rasul, M. G., Martens, W. N., Brown, R. and Hashib, M.A. (2010). Heterogeneous photocatalytic degradation of phenols in wastewater: a review on current status and developments. Desalination, 261(1–2): 3 – 18.

23. Soares, B. G., Amorim, G. S., Souza Jr, F. G., Oliveira M. G. and da Silva, J. E. P. (2006). The in situ poly-merization of aniline in nitrile rubber. Synthetic Metals, 156 (2–4): 91 – 98.

24. Zhao, R., Tan, C., Xie, Y., Gao, C., Liu, H. and Jiang, Y. (2011). One step synthesis of azo compounds from nitroaromatics and anilines, Tetrahedron Letter, 52(29): 3805 – 3809.

25. Puig, A., Ormad, P., Roche, P., Sarasa, J., Gimeno, E. and Ovelleiro, J. L. (1996). Wastewater from the manu-facture of rubber vulcanization accelerators: Characterization, downstream monitoring and chemical treatment. Journal of Chromatography A, 733 (1–2): 511 – 522.

26. Haque, E., Jun, J. W., Talapaneni, S. N., Vinu, A. and Jhung, S. H. (2010). Superior adsorption capacity of mesoporous carbon nitride with basic CN framework for phenol. Journal of Materials Chemistry, 20(48): 10801 – 10803.

27. Miller, D. R., Wang, J. and Gillan, E. G. (2002). Rapid, facile synthesis of nitrogen-rich carbon nitride powders. Journals of Materials Chemistry, 12(8): 2463 – 2469.