Naphthalimide–Rhodamine based chemosensors for colorimetric and fluorescent sensing Hg2+ through different signaling mechanisms in corresponding solvent systems

Abstract A couple of 1,8-naphthalimide–Rhodamine based chemosensors R6G-NA and RB-NA are successfully designed and synthesized with high selectivity and sensitivity to Hg 2+ . R6G-NA exhibits typical fluorescence resonance energy transfer (i.e. FRET) signal from 1,8-naphthalimide to Rhodamine 6G along with an obvious color change from yellow to orange when interacting with Hg 2+ in pure CH 3 CN. While RB-NA in CH 3 CN/HEPES buffer (1:1, v/v) can only act a photo-induced electron transfer off (i.e. PET-OFF) process in 1,8-naphthalimide with the fluorescence intensity centered at 525 nm increasing after adding Hg 2+ . However, in pure CH 3 CN system, the spirolactam ring of Rhodamine B in RB-NA can be opened by the Hg 2+ along with the block of PET process in 1,8-naphthalimide which leads to a new emission band emerging at 575 nm and the intensity of fluorescence enhancement at 515 nm together with the color clearly changing from yellow to pink.

[1]  Hong Zheng,et al.  Advances in modifying fluorescein and rhodamine fluorophores as fluorescent chemosensors. , 2013, Chemical communications.

[2]  Juyoung Yoon,et al.  Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives. , 2012, Chemical reviews.

[3]  A. Renzoni,et al.  Mercury levels along the food chain and risk for exposed populations. , 1998, Environmental research.

[4]  A. W. Damman,et al.  The biogeochemistry of an ombrotrophic bog: evaluation of use as an archive of atmosphere mercury deposition. , 1998, Environmental research.

[5]  Yasuhiro Shiraishi,et al.  Cu(II)-selective green fluorescence of a rhodamine-diacetic acid conjugate. , 2007, Organic letters.

[6]  Manoj Kumar,et al.  Naphthalimide appended rhodamine derivative: through bond energy transfer for sensing of Hg2+ ions. , 2011, Organic letters.

[7]  Joel H. Hildebrand,et al.  A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons , 1949 .

[8]  J. Choe,et al.  Synthesis of thionaphthalimides and their dual Hg2+-selective signaling by desulfurization of thioimides , 2013 .

[9]  T. Gunnlaugsson,et al.  Fluorescent Photoinduced Electron Transfer (PET) Sensors for Anions; From Design to Potential Application , 2005, Journal of Fluorescence.

[10]  M. Shortreed,et al.  Fluorescent fiber-optic calcium sensor for physiological measurements. , 1996, Analytical chemistry.

[11]  Ying Zhou,et al.  Cu2+-selective ratiometric and "off-on" sensor based on the rhodamine derivative bearing pyrene group. , 2009, Organic letters.

[12]  Yuan Fang,et al.  Visualizing Hg2+ ions in living cells using a FRET-based fluorescent sensor. , 2013, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[13]  G. Shen,et al.  Efficient fluorescence resonance energy transfer-based ratiometric fluorescent cellular imaging probe for Zn(2+) using a rhodamine spirolactam as a trigger. , 2010, Analytical chemistry.

[14]  R. Mclean,et al.  Removal of elemental mercury from wastewaters using polysulfides , 1981 .

[15]  Yufang Xu,et al.  "Alive" dyes as fluorescent sensors: fluorophore, mechanism, receptor and images in living cells. , 2010, Chemical communications.

[16]  X. Qian,et al.  A highly selective and sensitive fluorescent chemosensor for Hg2+ in neutral buffer aqueous solution. , 2004, Journal of the American Chemical Society.

[17]  Haibo Yu,et al.  Convenient and efficient FRET platform featuring a rigid biphenyl spacer between rhodamine and BODIPY: transformation of 'turn-on' sensors into ratiometric ones with dual emission. , 2011, Chemistry.

[18]  T. Duong,et al.  Fluoro- and chromogenic chemodosimeters for heavy metal ion detection in solution and biospecimens. , 2010, Chemical reviews.

[19]  Xiaoling Zhang,et al.  Ratiometric fluorescence chemosensors for copper(II) and mercury(II) based on FRET systems , 2010 .

[20]  Thorfinnur Gunnlaugsson,et al.  Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors. , 2010, Chemical Society reviews.

[21]  H. Thirsk,et al.  Passivation of mercury in sulfide ion solutions , 1968 .

[22]  Wei Huang,et al.  Inorganic-organic hybrid nanoprobe for NIR-excited imaging of hydrogen sulfide in cell cultures and inflammation in a mouse model. , 2014, Small.

[23]  T. Govindaraju,et al.  FRET-based rational strategy for ratiometric detection of Cu2+ and live cell imaging , 2013 .

[24]  H. Goicoechea,et al.  Rhodamine and BODIPY chemodosimeters and chemosensors for the detection of Hg2+, based on fluorescence enhancement effects , 2013 .

[25]  Jun Feng Zhang,et al.  Pyrene excimer-based calix[4]arene FRET chemosensor for mercury(II). , 2010, The Journal of organic chemistry.

[26]  Richa Rani,et al.  FRET-based ratiometric detection of Hg2+ and biothiols using naphthalimide-rhodamine dyads. , 2012, Organic & biomolecular chemistry.

[27]  J. Scaiano,et al.  Effect of cyclodextrin complexation on the photochemistry of xanthone. Absolute measurement of the kinetics for triplet-state exit , 1990 .

[28]  Manoj K. Kesharwani,et al.  Ratiometric detection of Cr3+ and Hg2+ by a naphthalimide-rhodamine based fluorescent probe. , 2012, Inorganic chemistry.

[29]  Muhammed Üçüncü,et al.  A rhodamine/BODIPY-based fluorescent probe for the differential detection of Hg(II) and Au(III). , 2014, Chemical communications.

[30]  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.

[31]  C. Afonso,et al.  Synthesis and applications of Rhodamine derivatives as fluorescent probes. , 2009, Chemical Society reviews.

[32]  Juyoung Yoon,et al.  A new trend in rhodamine-based chemosensors: application of spirolactam ring-opening to sensing ions. , 2008, Chemical Society reviews.

[33]  D. Karatza,et al.  Capture of mercury ions by natural and industrial materials. , 2006, Journal of hazardous materials.

[34]  Minghui Liu,et al.  A New Rhodamine B-coumarin Fluorochrome for Colorimetric Recognition of Cu 2+ and Fluorescent Recognition of Fe3+ in Aqueous Media , 2011 .

[35]  Juyoung Yoon,et al.  Recent progress on fluorescent chemosensors for metal ions , 2012 .

[36]  Yanlin Song,et al.  Highly Fluorescent Contrast for Rewritable Optical Storage Based on Photochromic Bisthienylethene-Bridged Naphthalimide Dimer , 2006 .

[37]  G. Shen,et al.  Through bond energy transfer: a convenient and universal strategy toward efficient ratiometric fluorescent probe for bioimaging applications. , 2012, Analytical chemistry.

[38]  Nantanit Wanichacheva,et al.  Dual optical Hg2+-selective sensing through FRET system of fluorescein and rhodamine B fluorophores , 2014 .

[39]  Xiaoling Zhang,et al.  A ratiometric fluorescent probe based on FRET for imaging Hg2+ ions in living cells. , 2008, Angewandte Chemie.

[40]  H. Tian,et al.  Near-infrared cell-permeable Hg2+-selective ratiometric fluorescent chemodosimeters and fast indicator paper for MeHg+ based on tricarbocyanines. , 2010, Chemistry.

[41]  J. Berg,et al.  Principles Of Bioinorganic Chemistry , 1994 .

[42]  Jing Liu,et al.  A naphthalimide–rhodamine ratiometric fluorescent probe for Hg2+ based on fluorescence resonance energy transfer , 2012 .

[43]  B. Valeur,et al.  Molecular Fluorescence: Principles and Applications , 2001 .

[44]  B. Ahamed,et al.  An integrated system of pyrene and rhodamine-6G for selective colorimetric and fluorometric sensing of mercury(II) , 2011 .

[45]  Yong Ye,et al.  A ratiometric fluorescent chemosensor for Hg2+ based on FRET and its application in living cells , 2014 .

[46]  Kwang Soo Kim,et al.  Rhodamine-based Hg2+-selective chemodosimeter in aqueous solution: fluorescent OFF-ON. , 2007, Organic letters.

[47]  Yuan Fang,et al.  Rhodamine–pyrene conjugated chemosensors for ratiometric detection of Hg2+ ions: Different sensing behavior between a spirolactone and a spirothiolactone , 2013 .

[48]  Jiasheng Wu,et al.  Calix[4]arene-based, Hg2+ -induced intramolecular fluorescence resonance energy transfer chemosensor. , 2007, The Journal of organic chemistry.

[49]  Qichun Zhang,et al.  Rhodamine-modified upconversion nanophosphors for ratiometric detection of hypochlorous acid in aqueous solution and living cells. , 2014, Small.

[50]  Igor L. Medintz,et al.  Materials for fluorescence resonance energy transfer analysis: beyond traditional donor-acceptor combinations. , 2006, Angewandte Chemie.

[51]  H. Tian,et al.  Near-IR core-substituted naphthalenediimide fluorescent chemosensors for zinc ions: ligand effects on PET and ICT channels. , 2010, Chemistry.

[52]  E. Akkaya,et al.  Design strategies for ratiometric chemosensors: modulation of excitation energy transfer at the energy donor site. , 2009, Journal of the American Chemical Society.

[53]  Daoben Zhu,et al.  A multianalyte chemosensor on a single molecule: promising structure for an integrated logic gate. , 2008, The Journal of organic chemistry.

[54]  Mei Chen,et al.  A Novel Hg2+ Selective Ratiometric Fluorescent Chemodosimeter Based on an Intramolecular FRET Mechanism , 2008, Journal of Fluorescence.

[55]  Xiaoling Zhang,et al.  Dithiolane linked thiorhodamine dimer for Hg2+ recognition in living cells. , 2009, Organic & biomolecular chemistry.

[56]  Huimin Ma,et al.  Rhodamine B thiolactone: a simple chemosensor for Hg2+ in aqueous media. , 2008, Chemical communications.