A Sensitive Ratiometric Fluorescent Sensor for Zinc(II) with High Selectivity

A new fluorescent Zn2+ chemosensor (P1) based on a functionalized porphyrin was synthesized and characterized. P1 displayed dramatic ratiometric variations in absorption and fluorescent emission spectra upon exposure to Zn2+ due to the formation of a 1:1 Zn2+/P1 complex. The sensor also exhibited high selectivity and sensitivity toward Zn2+ over other common metal ions in the physiological pH range with a detection limit of 1.8 μM. The sensor showed fast response times and excellent reproducibility, thus confirming its potential applicability as a fluorescent sensor for Zn2+ sensing.

[1]  J. B. Kim,et al.  A mechanistic study of the synthesis and spectral properties of meso-tetraarylporphyrins. , 1972, Journal of the American Chemical Society.

[2]  Ying Zhang,et al.  Colorimetric and Fluorescent Sensing of SCN- Based on meso-Tetraphenylporphyrin/meso-Tetraphenylporphyrin Cobalt(II) System , 2007, Sensors (Basel, Switzerland).

[3]  Hong-Seok Kim,et al.  Thiazole sulfonamide based ratiometric fluorescent chemosensor with a large spectral shift for zinc sensing , 2010 .

[4]  Q. Guo,et al.  Two-photon fluorescent probes of biological Zn(II) derived from 7-hydroxyquinoline. , 2009, Organic letters.

[5]  R. Purrello,et al.  Porphyrin assemblies as chemical sensors , 1999 .

[6]  R. Watts,et al.  Quantum efficiencies of transition metal complexes. III. Effect of ligand substituents on radiatiive and radiationless processes , 1972 .

[7]  Roger Y. Tsien,et al.  A New Cell-Permeable Fluorescent Probe for Zn2+ , 2000 .

[8]  Y. Urano,et al.  Improvement and biological applications of fluorescent probes for zinc, ZnAFs. , 2002, Journal of the American Chemical Society.

[9]  Zhaochao Xu,et al.  Exploiting the deprotonation mechanism for the design of ratiometric and colorimetric Zn2+ fluorescent chemosensor with a large red-shift in emission , 2006 .

[10]  J. Berg,et al.  The Galvanization of Biology: A Growing Appreciation for the Roles of Zinc , 1996, Science.

[11]  G. Shen,et al.  A porphyrin derivative containing 2-(oxymethyl)pyridine units showing unexpected ratiometric fluorescent recognition of Zn2+ with high selectivity. , 2008, Analytica chimica acta.

[12]  Shiva Agarwal,et al.  A Porphyrin Based Potentiometric Sensor for Zn2+ Determination , 2003 .

[13]  Yuqing Wu,et al.  Fluorescent chemosensor based on Schiff base for selective detection of zinc(II) in aqueous solution , 2010 .

[14]  Christopher J. Chang,et al.  Metals in Neurobiology: Probing Their Chemistry and Biology with Molecular Imaging , 2008 .

[15]  Jun Feng Zhang,et al.  Novel 2,2′-bipyridine-modified calix[4]arenes: ratiometric fluorescent chemosensors for Zn2+ ion , 2010 .

[16]  Weisheng Liu,et al.  Both visual and fluorescent sensor for Zn2+ based on quinoline platform. , 2010, Inorganic chemistry.

[17]  S. Kim,et al.  Dual-signaling fluorescent chemosensor based on bisthiazole derivatives , 2010 .

[18]  Min Xu,et al.  A new rhodamine-based chemosensor for Cu2+ and the study of its behaviour in living cells. , 2010, Dalton transactions.

[19]  Vlad Chiriac,et al.  A Novel Sensor for Monitoring of Iron(III) Ions Based on Porphyrins , 2012, Sensors.

[20]  Fengjuan Chen,et al.  A Highly Selective Fluorescent and Colorimetric Chemosensor for ZnII and Its Application in Cell Imaging , 2012 .

[21]  Hong-Seok Kim,et al.  Thiazole-based chemosensor: synthesis and ratiometric fluorescence sensing of zinc , 2009 .

[22]  He Tian,et al.  A selective fluorescent ratiometric chemodosimeter for mercury ion. , 2005, Chemical communications.

[23]  X. Tao,et al.  Synthesis, characterization, optical property of a bipyridine derivative and its application to determine trace Zn2+ in water , 2013 .

[24]  G. Shen,et al.  A ratiometric fluorescent sensor for zinc ions based on covalently immobilized derivative of benzoxazole. , 2009, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[25]  C. Redshaw,et al.  Ratiometric fluorescent receptors for both Zn2+ and H2PO4(-) ions based on a pyrenyl-linked triazole-modified homooxacalix[3]arene: a potential molecular traffic signal with an R-S latch logic circuit. , 2011, The Journal of organic chemistry.

[26]  X. Yao,et al.  A small molecular fluorescent sensor for highly selectivity of zinc ion , 2013 .

[27]  D. Spring,et al.  Zn2+-triggered amide tautomerization produces a highly Zn2+-selective, cell-permeable, and ratiometric fluorescent sensor. , 2010, Journal of the American Chemical Society.

[28]  D. Spring,et al.  Coumarin-derived transformable fluorescent sensor for Zn2+. , 2012, Chemical communications.

[29]  Shaobin Huang,et al.  A new Zn2+ chemosensor based on functionalized 8-hydroxylquinoline , 2010 .

[30]  J. Demas,et al.  Quantum efficiencies of transition-metal complexes. I. d-d Luminescence , 1970 .

[31]  Palanisamy Kalimuthu,et al.  Optochemical sensing of hydrogen chloride gas using meso-tetramesitylporphyrin deposited glass plate. , 2008, Analytica chimica acta.

[32]  S. Mashraqui,et al.  A new internal charge transfer probe for the highly selective detection of Zn(II) by means of dual colorimetric and fluorescent turn-on responses , 2012 .

[33]  X. Yao,et al.  A Highly Zinc(II)‐Selective Fluorescent Sensor Based on 8‐Aminoquinoline and Its Application in Biological Imaging , 2011 .

[34]  A. Ajayaghosh,et al.  A ratiometric fluorescence probe for selective visual sensing of Zn2+. , 2005, Journal of the American Chemical Society.

[35]  Yuncong Chen,et al.  A sulfonamidoquinoline-derived Zn2+ fluorescent sensor with 1:1 Zn2+ binding stoichiometry , 2011 .

[36]  Baoxiang Zhao,et al.  Novel pyrazoline-based selective fluorescent sensor for Zn2+ in aqueous media , 2011 .

[37]  B. Imperiali,et al.  Modular and tunable chemosensor scaffold for divalent zinc. , 2003, Journal of the American Chemical Society.

[38]  Yixiang Cheng,et al.  A highly selective ratiometric fluorescent chemosensor for Zn2+ ion based on a polyimine macrocycle , 2012 .

[39]  W. Chan,et al.  Both visual and ratiometric fluorescent sensor for Zn2+ based on spirobenzopyran platform , 2012 .

[40]  D. Spring,et al.  Fluorescent Chemosensors for Zn2 , 2010 .

[41]  D. Spring,et al.  Fluorescent chemosensors for Zn(2+). , 2010, Chemical Society reviews.

[42]  S. Quici,et al.  A critical evaluation of EFISH and THG non-linear optical responses of asymmetrically substituted meso-tetraphenyl porphyrins and their metal complexes , 2002 .

[43]  C. Choi,et al.  New regioisomeric naphthol-substituted thiazole based ratiometric fluorescence sensor for Zn2+ with a remarkable red shift in emission spectra , 2012 .