Abstract
A new rhodamine-based Hg2+-selective fluorescent probe (I) was designed and synthesized. Compound I displays excellent selective and sensitive response to Hg2+ over other transition metal ions in neutral aqueous solutions. I itself is a colorless, nonfluorescent compound. Upon addition of Hg2+ to its solution, the thiosemicarbazide moiety of I undergoes an irreversible desulfurization reaction to form the corresponding 1,3,4-oxadiazole (II), a colorful and fluorescent product, causing instantaneous development of visible color and strong fluorescence emission. Based on this mechanism, a fluorogenic probe for Hg2+ was developed. The fluorescence increases linearly with the Hg2+ concentration up to 0.8 μmol L−1 with the detection limit of 9.4 nmol L− (3σ).
Similar content being viewed by others
References
Bae, S., & Tae, J. (2007). Rhodamine-hydroxamate-based fluorescent chemosensor for Fe(III). Tetrahedron Letters, 48, 5389–5392. DOI:10.1016/j.tetlet.2007.06.014.
Chae, M. Y., & Czarnik, A. W. (1992). Fluorimetric chemodosimetry. Mercury(II) and silver(I) indication in water via enhanced fluorescence signaling. Journal of the American Chemical Society, 114, 9704–9705. DOI: 10.1021/ja00050a085.
Coronado, E., Galán-Mascarós, J. R., Martí-Gastaldo, C., Palomares, E., Durrant, J. R., Vilar, R., Gratzel, M., & Nazeeruddin, M. K. (2005). Reversible colorimetric probes for mercury sensing. Journal of the American Chemical Society, 127, 12351–12356. DOI: 10.1021/ja0517724.
De Santis, G. D., Fabbrizzi, L., Licchelli, M., Mangano, C., & Sacchi, D. (1995). Redox switching of anthracene fluorescence through the Cu(II)/Cu(I) couple. Inorganic Chemistry, 34, 3581–3582. DOI: 10.1021/ic00118a003.
Dujols, V., Ford, F., & Czarnik, A. W. (1997). A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water. Journal of the American Chemical Society, 119, 7386–7387. DOI: 10.1021/ja971221g.
Erxleben, H., & Ruzicka, J. (2005). Atomic absorption spectroscopy for mercury, automated by sequential injection and miniaturized in lab-on-valve system. Analytical Chemistry, 77, 5124–5128. DOI: 10.1021/ac058007s.
Guo, X. F., Qian, X. H., & Jia, L. H. (2004). A highly selective and sensitive fluorescent chemosensor for Hg2+ in neutral buffer aqueous solution. Journal of the American Chemical Society, 126, 2272–2273. DOI: 10.1021/ja037604y.
Ha-Thi, M. H., Penhoat, M., Michelet, V., & Leray, I. (2007). Highly selective and sensitive phosphane sulfide derivative for the detection of Hg2+ in an organoaqueous medium. Organic Letters, 9, 1133–1136. DOI: 10.1021/ol070118l.
Ko, S.-K., Yang, Y.-K., Tae, J., & Shin, I. (2006). In vivo monitoring of mercury ions using a rhodamine-based molecular probe. Journal of the American Chemical Society, 128, 14150–14155. DOI: 10.1021/ja065114a.
Kwon, J. Y., Jang, Y. J., Lee, Y. J., Kim, K. M., Seo, M. S., Nam, W., & Yoon, J. (2005). A highly selective fluorescent chemosensor for Pb2+. Journal of the American Chemical Society, 127, 10107–10111. DOI: 10.1021/ja051075b.
Lee, M. H., Cho, B. K., Yoon, J., & Kim, J. S. (2007). Selectively chemodosimetric detection of Hg(II) in aqueous media. Organic Letters, 9, 4515–4518. DOI: 10.1021/ol7020115.
Lee, M. H., Wu, J.-S., Lee, J. W., Jung, J. H., & Kim, J. S. (2007). Highly sensitive and selective chemosensor for Hg2+ based on the rhodamine fluorophore. Organic Letters, 9, 2501–2504. DOI: 10.1021/ol0708931.
Li, Y., Jiang, Y., & Yan, X. P. (2006). Probing mercury species-DNA interactions by capillary electrophoresis with on-line electrothermal atomic absorption spectrometric detection. Analytical Chemistry, 78, 6115–6120. DOI: 10.1021/ac060644a.
Liu, B., & Tian, H. (2005). A selective fluorescent ratiometric chemodosimeter for mercury ion. Chemical Communications, 2005, 3156–3158. DOI: 10.1039/b501913c.
Long, S. E., & Kelly, W. R. (2002). Determination of mercury in coal by isotope dilution cold-vapor generation inductively coupled plasma mass spectrometry. Analytical Chemistry, 74, 1477–1483. DOI: 10.1021/ac010954n.
Mahajan, R. K., Kaur, R., Bhalla, V., Kumar, M., Hattori, T., & Miyano, S. (2008). Mercury(II) sensors based on calix[4]arene derivatives as receptor molecules. Sensors and Actuators B, 130, 290–294. DOI: 10.1016/j.snb.2007.08.006.
Mao, J., Wang, L. N., Dou, W., Tang, X. L., Yan, Y., & Liu, W. S. (2007). Tuning the selectivity of two chemosensors to Fe(III) and Cr(III). Organic Letters, 9, 4567–4570. DOI: 10.1021/ol7020687.
Mei, L., Xiang, Y., Li, N., & Tong, A. J. (2007). A new fluorescent probe of rhodamine B derivative for the detection of copper ion. Talanta, 72, 1717–1722. DOI: 10.1016/j.talanta. 2007.02.002.
Nolan, E. M., Racine, M. E., & Lippard, S. J. (2006). Selective Hg(II) detection in aqueous solution with thiol derivatized fluoresceins. Inorganic Chemistry, 45, 2742–2749. DOI: 10.1021/ic052083w.
Ros-Lis, J. V., Marcos, M. D., Mártinez-Máńez, R., Rurack, K., & Soto, J. (2005). A regenerative chemodosimeter based on metal-induced dye formation for the highly selective and sensitive optical determination of Hg2+ ions. Angewandte Chemie International Edition, 44, 4405–4407. DOI: 10.1002/anie.200500583.
Sheng, R. L., Wang, P. F., Liu, W. M., Wu, X. H., & Wu, S. K. (2008). A new colorimetric chemosensor for Hg2+ based on coumarin azine derivative. Sensors and Actuators B, 128, 507–511. DOI: 10.1016/j.snb.2007.07.069.
Shi, W., & Ma, H. M. (2008). Rhodamine B thiolactone: a simple chemosensor for Hg2+ in aqueous media. Chemical Communications, 2008, 1856–1858. DOI: 10.1039/b717718f
Smith, R. C., Tennyson, A. G., Lim, M. H., & Lippard, S. J. (2005). Conjugated polymer-based fluorescence turn-on sensor for nitric oxide. Organic Letters, 7, 3573–3575. DOI: 10.1021/ol0513903.
Soh, J. H., Swamy, K. M. K., Kim, S. K., Kim, S., Lee, S. H., & Yoon, J. (2007). Rhodamine urea derivatives as fluorescent chemosensors for Hg2+. Tetrahedron Letters, 48, 5966–5969. DOI: 10.1016/j.tetlet.2007.06.114.
Song, K. C., Kim, J. S., Park, S. M., Chung, K. C., Ahn, S., & Chang, S. K. (2006). Fluorogenic Hg2+-selective chemodosimeter derived from 8-hydroxyquinoline. Organic Letters, 8, 3413–3416. DOI: 10.1021/ol060788b.
Wu, D., Huang, W., Duan, C., Lin, Z., & Meng, Q. (2007a). Highly sensitive fluorescent probe for selective detection of Hg2+ in DMF aqueous media. Inorganic Chemistry, 46, 1538–1540. DOI: 10.1021/ic062274e.
Wu, J.-S., Hwang, I.-C., Kim, K. S., & Kim, J. S. (2007b). Rhodamine-based Hg2+-selective chemodosimeter in aqueous solution: fluorescent OFF-ON. Organic Letters, 9, 907–910. DOI: 10.1021/ol070109c.
Xiang, Y., Mei, L., Li, N., & Tong, A. J. (2007). Sensitive and selective spectrofluorimetric determination of chromium(VI) in water by fluorescence enhancement. Analytica Chimica Acta, 581, 132–136. DOI: 10.1016/j.aca.2006.08.006.
Xiang, Y., & Tong, A. J. (2006). A new rhodamine-based chemosensor exhibiting selective Fe(III)-amplified fluorescence. Organic Letters, 8, 1549–1552. DOI: 10.1021/ol060001h.
Xiang, Y., & Tong, A. J. (2008). Ratiometric and selective fluorescent chemodosimeter for Cu(II) by Cu(II)-induced oxidation. Luminescence, 23, 28–31. DOI: 10.1002/bio.1012.
Xiang, Y., Tong, A. J., Jin, P. Y., & Ju, Y. (2006). New fluorescent rhodamine hydrazone chemosensor for Cu(II) with high selectivity and sensitivity. Organic Letters, 8, 2863–2866. DOI: 10.1021/ol0610340.
Yang, H., Zhou, Z. G., Huang, K. W., Yu, M. X., Li, F. Y., Yi, T., & Huang, C. H. (2007). Multisignaling optical-electrochemical sensor for Hg2+ based on a rhodamine derivative with a ferrocene unit. Organic Letters, 9, 4729–4732. DOI: 10.1021/ol7020143.
Yang, X. F., Guo, X. Q., & Zhao, Y. B. (2002). Development of a novel rhodamine-type fluorescent probe to determine peroxynitrite. Talanta, 57, 883–890. DOI: S0039-9140(02)00120-0.
Yang, X. F., Li, Y., & Bai, Q. (2007). A highly selective and sensitive fluorescein-based chemodosimeter for Hg2+ ions in aqueous media. Analytica Chimica Acta, 584, 95–100. DOI: 10.1016/j.aca.2006.11.015.
Yang, Y.-K., Yook, K.-J., & Tae, J. (2005). A rhodamine-based fluorescent and colorimetric chemodosimeter for the rapid detection of Hg2+ ions in aqueous media. Journal of the American Chemical Society, 127, 16760–16761. DOI: 10.1021/ja054855t.
Yoon, S., Miller, E. W., He, Q. W., Patrick, H. D., & Chang, C. J. (2007). A bright and specific fluorescent sensor for mercury in water, cells, and tissue. Angewandte Chemie International Edition, 46, 6658–6661. DOI: 10.1002/anie.200701785.
Yu, Y., Lin, L. R., Yang, K. B., Zhong, X., Huang, R. B., & Zheng, L. S. (2006). p-Dimethylaminobenzaldehyde thiosemicarbazone: A simple novel selective and sensitive fluorescent sensor for mercury(II) in aqueous solution. Talanta, 69, 103–106. DOI: 10.1016/j.talanta.2005.09.015.
Yuan, M. J., Li, Y. L., Li, J. B., Li, C. H., Liu, X. F., Lv, J., Xu, J. L., Liu, H. B., Wang, S., & Zhu, D. B. (2007). A colorimetric and fluorometric dual-modal assay for mercury ion by a molecule. Organic Letters, 9, 2313–2316. DOI: 10.1021/ol0706399.
Zhan, X. Q., Qian, Z. H., Zheng, H., Su, B. Y., Lan, Z., & Xu, J. G. (2008). Rhodamine thiospirolactone. Highly selective and sensitive reversible sensing of Hg(II). Chemical Communications, 2008, 1859–1861. DOI: 10.1039/b719473k.
Zhang, G. X., Zhang, D. Q., Yin, S. W., Yang, X. D., Shuai, Z. G., & Zhu, D. B. (2005). 1,3-Dithiole-2-thione derivatives featuring an anthracene unit: new selective chemodosimeters for Hg(II) ion. Chemical Communications, 2005, 2161–2163. DOI: 10.1039/b417952h.
Zhang, M., Gao, Y. H., Li, M. Y., Yu, M. X., Li, F. Y., Li, L., Zhu, M. W., Zhang, J. P., Yi, T., & Huang, C. H. (2007). A selective turn-on fluorescent sensor for FeIII and application to bioimaging. Tetrahedron Letters, 48, 3709–3712. DOI: 10.1016/j.tetlet.2007.03.112.
Zhang, X., Shiraishi, Y., & Hirai, T. (2007). Cu(II)-selective green fluorescence of a rhodamine-diacetic acid conjugate. Organic Letters, 9, 5039–5042. DOI: 10.1021/ol7022714.
Zheng, H., Qian, Z. H., Xu, L., Yuan, F. F., Lan, L. D., & Xu, J. G. (2006). Switching the recognition preference of rhodamine B spirolactam by replacing one atom: design of rhodamine B thiohydrazide for recognition of Hg(II) in aqueous solution. Organic Letters, 8, 859–861. DOI: 10.1021/ol0529086.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Zhao, M., Yang, XF., He, S. et al. A rhodamine-based Hg2+-selective fluorescent probe in aqueous solution. Chem. Pap. 63, 261–267 (2009). https://doi.org/10.2478/s11696-009-0016-8
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11696-009-0016-8