Abstract
The hexapodal Rhodamine B derivative compound 3 containing a cyclotriphosphazene core was synthesized and characterized by spectroscopic techniques such as FT-IR, 1H, 13C and 31P NMR, HR-MS, MALDI MS and microanalysis. Compound 3 is a naked eye selective sensor with colorimetric and fluorescent properties for Hg2+ ions in the presence of other metal ions such as Na+, K+, Ca2+, Ba2+, Mg2+, Ag+, Mn2+, Cu2+, Ni2+, Co2+, Pb2+, Cd2+, Zn2+, Fe2+, Fe3+, and Cr3+. The optical sensor properties of compound 3 were investigated using UV–vis and fluorescence spectroscopy. The lowest detection limit of compound 3 was determined as 3.76 × 10−9 M (0.75 ppb) for Hg2+ ions. The stoichiometry of compound 3-Hg2+ complex was found to be 1:3 (ligand/metal ion). The reusable test strip was improved by the immobilization of compound 3 into a hydrogel network. The reusability of the sensor and test strip was tested with S2− ion solutions.
Similar content being viewed by others
References
Gupta A, Vidyarthi SR, Sankararamakrishnan N (2014) Enhanced sorption of mercury from compact fluorescent bulbs and contaminated water streams using functionalized multiwalled carbon nanotubes. J Hazard Mater 274:132–144
Nolan EM, Lippard SJ (2008) Tools and tactics for the optical detection of mercury ion. Chem Rew 108:3443–3480
Borrell A, Aguilar A, Tornero V, Drago M (2014) Concentrations of mercury in tissues of striped dolphins suggest decline of pollution in Mediterranean open waste. Chemosphere 107:319–323
Guedron S, Tisserand D, Grambois S, Spadini L, Molton F, Bounvilay B, Charlet L, Polya DA (2014) Baseline investigation of (methyl) mercury in waters, solils, sediments and key foodstuffs in the Lower Mekong Basin: The rapidly developing city of Vientiane (Lao PDR). J Geochem Expl 143:96–102
Cho JH, Eom Y, Lee TG (2014) Stabilization/solidification of mercury-contaminated waste ash using calcium sodium phosphate (CNP) and magnesium potassium phosphate (MKP) processes. J Hazard Mater 278:474–482
Renzoni A, Zino F, Franchi E (1998) Mercury levels along the food chain and risk for exposed population. Environ Res 77:68–72
Raimundo J, Pereira P, Vale C, Canario J, Gaspar M (2014) Relations between total mercury, methylmercury and selenium in five tissue of Sepia officinalis captured in the south Portuguese coast. Chemosphere 108:190–196
Li P, Feng XB, Qui GL, Shang LH, Li ZG (2009) Mercury pollution in Asia: A review of the contaminated sites. J Hazard Mater 168:591–601
Li Z, Wu L, Liu H, Lan H, Qu J (2013) Improvement of aqueous mercury adsorption on activated coke by thiol-functionalization. Chem Eng J 228:925–934
Shenashen MA, Elshehy EA, El-Safty SA, Khairy M (2013) Visual monitoring and removal of divalent copper, cadmium and mercury ions from water by using mesoporous cubic la3d aluminosilica sensors. Sep Purif Technol 116:73–86
Wang W, Chen M, Chen X, Wang J (2014) Thiol-rich polyhedral oligomeric silsesquioxane as a novel adsorbent for mercury adsorption and speciation. Chem Eng J 242:62–68
Punrat E, Chuanuwatanakul S, Kaneta T, Motomizu S, Chailapakul O (2014) Method development for the determination of mercury (II) by sequential injection/anodic stripping voltammetry using an in situ gold-film screen-printed carbon electrode. J Electroanal Chem 727:78–83
Srungaram PK, Ayyalasomayajula KK, Yu-Yueh F, Sing JP (2013) Comparison of laser induced breakdown spectroscopy and spark induced breakdown spectroscopy for determination of mercury in soils. Spectrochim Acta Part B 87:108–113
Zmozinski AV, Carneado S, Palomino CI, Sahuquillo A, Sanchez JFL, Silva MM (2014) Method development for the simultaneous determination of methylmercury and inorganic mercury in seafood. Food Control 46:351–359
Wang M, Zhang D, Li M, Fan M, Ye Y, Zhao Y (2013) A rhodamine-cyclen conjugate as chromogenic and fluorescent chemosensor for copper ion in aqueous media. J Fluoresc 23:417–423
Dong Z, Tian X, Chen Y, Hou J, Guo Y, Sun J, Ma J (2013) A highly selective fluorescent chemosensor for Hg2+ based on rhodamine B and its application as a molecular logic gate. Dyes Pigm 97:324–329
Li KB, Zhang HL, Zhu B, He XP, Xie J, Chen GR (2014) A per-acetyl glycosyl rhodamine as a novel fluorescent ratiometric probe for mercury (II). Dyes Pigm 102:273–277
Zhou X, Yan W, Zhao T, Tian Z, Wu X (2013) Rhodamine based derivative and its zinc complex: synthesis and recognition behavior toward Hg (II). Tetrahedron 69:9535–9539
Huang W, Zhou P, Yan W, He C, Xiong L, Li F, Duan C (2009) A bright water-compatible sugar-rhodamine fluorescence sensor for selective detection of Hg2+ in natural water and living cells. J Environ Monit 11:330–335
Chu KH, Zhou Y, Fang Y, Wang LH, Li JY, Yao C (2013) Rhodamine-pyrene conjugated chemosensors for ratiometric detection of Hg2+ ions: Different sensing behavior between a spirolactone and a spirothiolactone. Dyes Pigm 98:339–346
Cheng ZH, Li G, Zhang N, Liu HO (2014) A novel functionalized silver nanoparticles solid chemosensor for detection of Hg (II) in aqueous media. Dalton Trans 43:4762–4769
Huang W, Wu D, Wu G, Wang Z (2012) Dual functional rhodamine-immobilized silica toward sensing and extracting mercury ions in natural water samples. Dalton Trans 41:2620–2625
Allcock HR (2013) Generation of structural diversity in polyphosphazenes. Appl Organomet Chem 27:620–629
Kagit R, Yildirim M, Ozay O, Yesilot S, Ozay H (2014) Phosphazene based multicentered naked-eye fluorescent sensor with high selectivity for Fe3+ ions. Inorg Chem 53:2144–2151
Caminade AM, Majoral JP (2013) Positively charged phosphorus dendrimers. An overview of their properties. New J Chem 37:3358–3373
Badetti E, Lloveras V, Wurst K, Sebastian RM, Caminade AM, Majoral JP, Veciana J, Vidal-Gancedo J (2013) Synthesis and structural characterization of a dendrimer model compound based on a cyclotriphosphazene core with tempo radicals as substituents. Org Lett 15:3490–3493
Keller M, Colliere V, Reiser O, Caminade AM, Majoral JP, Ouali A (2013) Pyrene-tagged dendritic catalysts noncovalently grafted onto magnetic Co/C nanoparticles: An efficient and recyclable system for drug synthesis. Angew Chem Int Ed 52:3626–3629
Ozay H, Ozay O (2014) Synthesis and characterization of drug microspheres containing phosphazene for biomedical applications. Colloids Surf A 450:99–105
Bolink HJ, Santamaria SG, Sudhakar S, Zhen C, Sellinger A (2008) Solution processable phosphorescent dendrimers based on cyclic phosphazenes for use in organic light emitting diodes (OLEDs). Chem Commun 2008:618–620
Zhang D, Li M, Jiang Y, Wang C, Wang Z, Ye Y (2013) A new sensitive and selective chromogenic and fluorescent chemodosimeter for Hg (II) in aqueeous media and its application in live cell imaging. Dyes Pigm 99:607–612
Wang M, Yan F, Zou Y, Chen L, Yang N, Zhou X (2014) Recognition of Cu2+ in physiological conditions by a new rhodamine based dual channel fluorescent probe. Sens Actuators B 192:512–521
Yan F, Cao D, Yang N, Wang M, Dai L, Li C, Chen L (2013) A rhodamine based fluorescent probe for Hg2+ and its application to cellular imaging. Spectrochim Acta Part A 106:19–24
Wang M, Yan FY, Zou Y, Yang N, Chen L, Chen LG (2014) A rhodamine derivative as selective fluorescent and colorimetric chemosensor for mercury (II) in buffer solution, test strips and living cells. Spectrochim Acta Part A 123:216–223
Bhalla V, Vij V, Tejpal R, Singh G, Kumar M (2013) Solvent dependent competition between fluorescence resonance energy transfer and through bond energy transfer in rhodamine appended hexaphenylbenzene derivatives for sensing of Hg2+ ions. Dalton Trans 42:4456–4463
Park S, Kim W, Swamy KMK, Lee HY, Jung JY, Kim G, Kim Y, Kim SJ, Yoon J (2013) Rhodamine hydrazone derivatives bearing thiophene group as fluorescent chemosensors for Hg2+. Dyes Pigm 99:323–328
Mandal S, Banerjee A, Lohar S, Chattopadhyay A, Sarkar B, Mukhopadhyay SK, Sahana A, Das D (2013) Selective sensing of Hg2+ using rhodamine- thiophene conjugate: Red light emission and visual detection of intracellular Hg2+ at nanomolar level. J Hazard Mater 261:198–205
Wang HF, Wu SP (2013) Highly selective fluorescent sensors for mercury (II) ions and their applications in living cell imaging. Tetrahedron 69:1965–1969
Li L-Q, Meng L-P (2014) A selective fluorescent sensor for Hg2+. J Fluoresc 24:301–303
Ozay H, Ozay O (2013) Rhodamine based reusable and colorimetric naked-eye hydrogel sensors for Fe3+ ion. Chem Eng J 232:364–371
Acknowledgements
This work was financially supported by the Scientific and Technological Research Council of Turkey (TUBITAK, Project 112 T278).
Electronic supplementary material
The online version of this article contains supplementary material, which is available to authorized users.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
ESM 1
(DOCX 1085 kb)
Rights and permissions
About this article
Cite this article
Ozay, H., Kagit, R., Yildirim, M. et al. Novel hexapodal triazole linked to a cyclophosphazene core rhodamine-based chemosensor for selective determination of Hg2+ ions. J Fluoresc 24, 1593–1601 (2014). https://doi.org/10.1007/s10895-014-1444-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-014-1444-6