A sandwich-type zinc complex from a rhodamine dye based ligand: a potential fluorescent chemosensor for acetate in human blood plasma and a molecular logic gate with INHIBIT function

A new fluorescent zinc complex Zn-R1 based on rhodamine-tris(hydroxymethyl)aminomethane spirolactam ligand R has been synthesised and characterised. Single crystal X-ray diffraction analyses revealed that in this complex R exists in its ring opened spirolactam form R1 and the complex Zn-R1 has a distinctive geometry in which the Zn2+ ion is sandwiched between the dye motifs of two R1 ligands. Zn-R1 exhibits very strong orange fluorescence and pink colour in acetonitrile : H2O (9.5 : 0.5%, v/v) solutions and the addition of acetate ions causes quenching of the fluorescence accompanied by a colour change from pink to colourless. The mode of interaction between Zn-R1 and acetate ions has been confirmed by absorption, fluorescence, NMR and HR-MS techniques. Further, Zn-R1 is highly selective towards acetate ions and exhibits potential as a sensor for acetate in solid state and in solutions including human blood plasma-like systems. The reversibility of acetate binding by Zn-R1 is demonstrated by adding an excess of acetate and Zn2+ ions alternately to the solution of Zn-R1 for multiple times. The fluorescence output shown by Zn-R1 on addition/non-addition of Zn2+ and acetate ions as sequential inputs can be used to construct an INHIBIT type molecular logic gate.

[1]  M. Devi,et al.  A Tris(hydroxymethyl)aminomethane‐Rhodamine Spirolactam Derivative as Dual Channel pH and Water Sensor and Its Application to Bio Imaging , 2015 .

[2]  Y. Son,et al.  A highly selective fluorescent chemosensor for Hg2+ based on a squaraine–bis(rhodamine-B) derivative: Part II , 2015 .

[3]  Manoj Kumar,et al.  A thiacalix[4]crown based chemosensor for Zn²⁺ and H₂PO₄⁻: sequential logic operations at the molecular level. , 2015, Dalton transactions.

[4]  Xingjiang Liu,et al.  Naked-eye-based selective detection of pyrophosphate with a Zn2+ complex in aqueous solution and electrospun nanofibers , 2015 .

[5]  Weihong Zhu,et al.  Fluorescent and colorimetric ion probes based on conjugated oligopyrroles. , 2015, Chemical Society reviews.

[6]  Xiaoya Liu,et al.  Highly cross-linked fluorescent poly(cyclotriphosphazene-co-curcumin) microspheres for the selective detection of picric acid in solution phase , 2015 .

[7]  Kiran Singh,et al.  A new rhodamine derivative as a single optical probe for the recognition of Cu2+ and Zn2+ ions , 2015 .

[8]  A. Gupta,et al.  Ratiometric Detection of Adenosine‐5′‐triphosphate (ATP) and Cytidine‐5′‐triphosphate (CTP) with a Fluorescent Spider‐Like Receptor in Water , 2015 .

[9]  N. Guchhait,et al.  A unique rhodamine-based ‘off–on’ molecular spy for selective detection of trivalent aluminum and chromium ions: Synthesis, crystal structure and spectroscopic properties along with living cell imaging , 2014 .

[10]  Chuluo Yang,et al.  Yellow/orange emissive heavy-metal complexes as phosphors in monochromatic and white organic light-emitting devices. , 2014, Chemical Society reviews.

[11]  Hong-Yan Zhang,et al.  A new fluorescent probe for Al(3+) based on rhodamine 6G and its application to bioimaging. , 2014, Dalton transactions.

[12]  Pooja,et al.  New triangular steroid-based A(LS)3 type gelators for selective fluoride sensing application , 2014 .

[13]  A. Misra,et al.  An efficient multichannel probe to detect anions in different media and its real application in human blood plasma , 2014 .

[14]  Pooja,et al.  A cytochrome C encapsulated metal organic framework as a bio-material for sulfate ion recognition , 2014 .

[15]  C. Pradeep,et al.  Nano dispersion of 3D Cd(II) coordination polymer: synthetic blood plasma anticoagulant , 2014 .

[16]  Shilpa Sharma,et al.  ESIPT induced AIEE active material for recognition of 2-thiobarbituric acid , 2014 .

[17]  Yongshu Xie,et al.  Macrocycle contraction and expansion of a dihydrosapphyrin isomer. , 2013, Journal of the American Chemical Society.

[18]  Weihong Zhu,et al.  Steric hindrance-enforced distortion as a general strategy for the design of fluorescence "turn-on" cyanide probes. , 2013, Chemical communications.

[19]  Chirantan Kar,et al.  Zn2+ and pyrophosphate sensing: selective detection in physiological conditions and application in DNA-based estimation of bacterial cell numbers. , 2013, Analytical chemistry.

[20]  A. Gupta,et al.  A fluorescence 'turn-on' chemodosimeter for selective detection of Nb5+ ions in mixed aqueous media. , 2013, Dalton transactions.

[21]  D. Spiegel,et al.  A "turn-on" fluorescent sensor for methylglyoxal. , 2013, Journal of the American Chemical Society.

[22]  N. Bell,et al.  Homoleptic 'sandwich' complexes of substituted tris(methimazolyl)borate ligands with ruthenium, rhodium and palladium. , 2013, Dalton transactions.

[23]  Weihong Zhu,et al.  α-Monoacylated and α,α'- and α,β'-diacylated dipyrrins as highly sensitive fluorescence "turn-on" Zn2+ probes. , 2013, The Journal of organic chemistry.

[24]  M. Devi,et al.  Au microparticles mediated construction of a logic based dual channel molecular keypad lock. , 2013, Dalton transactions.

[25]  A. Banerjee,et al.  A naphthalene-thiophene hybrid molecule as a fluorescent AND logic gate with Zn2+ and OAc- ions as inputs: cell imaging and computational studies. , 2013, Dalton transactions.

[26]  A. Banerjee,et al.  Rhodamine-based fluorescent probe for Al3+ through time-dependent PET-CHEF-FRET processes and its cell staining application. , 2013, Inorganic chemistry.

[27]  Zijian Guo,et al.  Metal coordination in photoluminescent sensing. , 2013, Chemical Society reviews.

[28]  Weihong Zhu,et al.  Selective, sensitive and reversible "turn-on" fluorescent cyanide probes based on 2,2'-dipyridylaminoanthracene-Cu2+ ensembles. , 2012, Chemical communications.

[29]  Lei Zhu,et al.  Tricolor emission of a fluorescent heteroditopic ligand over a concentration gradient of zinc(II) ions. , 2012, The Journal of organic chemistry.

[30]  K. Jolliffe,et al.  Anion recognition and sensing with Zn(II)-dipicolylamine complexes. , 2012, Chemical Society reviews.

[31]  Jim A. Thomas,et al.  Ruthenium(II) polypyridyl complexes and DNA--from structural probes to cellular imaging and therapeutics. , 2012, Chemical Society reviews.

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

[33]  Bing Yin,et al.  Three rhodamine-based "off-on" chemosensors with high selectivity and sensitivity for Fe3+ imaging in living cells. , 2012, The Journal of organic chemistry.

[34]  Manoj Kumar,et al.  New terphenyl based mercury ensemble for detection of acetate ions in a plasma like system. , 2012, Dalton transactions.

[35]  Yun Zhao,et al.  A Cu(II)-based chemosensing ensemble bearing rhodamine B fluorophore for fluorescence turn-on detection of cyanide , 2012 .

[36]  Xiaoling Zhang,et al.  A copper(II) rhodamine complex with a tripodal ligand as a highly selective fluorescence imaging agent for nitric oxide. , 2011, Chemical communications.

[37]  Weihong Zhu,et al.  Selective and sensitive "turn-on" fluorescent Zn2+ sensors based on di- and tripyrrins with readily modulated emission wavelengths. , 2011, Chemical communications.

[38]  Yong-Cheng Feng,et al.  A novel colorimetric and fluorescent chemosensor for acetate ions in aqueous media based on a rhodamine 6G-phenylurea conjugate in the presence of Fe(III) ions. , 2011, Chemical communications.

[39]  C. Huang,et al.  A molecular logic gate for the highly selective recognition of pyrophosphate with a hypocrellin A-Zn(II) complex. , 2010, The Analyst.

[40]  Fuyou Li,et al.  Phosphorescent chemosensors based on heavy-metal complexes. , 2010, Chemical Society reviews.

[41]  Juyoung Yoon,et al.  Colorimetric and fluorescent sensing of pyrophosphate in 100% aqueous solution by a system comprised of rhodamine B compound and Al3+ complex. , 2010, The Analyst.

[42]  B. Tang,et al.  A superamplification effect in the detection of explosives by a fluorescent hyperbranched poly(silylenephenylene) with aggregation-enhanced emission characteristics , 2010 .

[43]  K. Shimizu,et al.  Toward the development of prochelators as fluorescent probes of copper-mediated oxidative stress. , 2010, Dalton transactions.

[44]  Wei Huang,et al.  Structural modification of rhodamine-based sensors toward highly selective mercury detection in mixed organic/aqueous media. , 2009, Dalton transactions.

[45]  J. Qin,et al.  A new rhodamine-based colorimetric cyanide chemosensor: convenient detecting procedure and high sensitivity and selectivity. , 2009, ACS applied materials & interfaces.

[46]  B. Tang,et al.  Cu2+-selective naked-eye and fluorescent probe: its crystal structure and application in bioimaging. , 2009, The Analyst.

[47]  Richard J. Gildea,et al.  OLEX2: a complete structure solution, refinement and analysis program , 2009 .

[48]  R. Goyal,et al.  Anion recognition using newly synthesized hydrogen bonding disubstituted phenylhydrazone-based receptors: poly(vinyl chloride)-based sensor for acetate. , 2008, Talanta.

[49]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[50]  Yasuhiro Shiraishi,et al.  Unmodified fluorescein as a fluorescent chemosensor for fluoride ion detection , 2007 .

[51]  Jiasheng Wu,et al.  Anion-induced ring-opening of fluorescein spirolactam: fluorescent OFF-ON , 2007 .

[52]  Galina Melman,et al.  A molecular keypad lock: a photochemical device capable of authorizing password entries. , 2007, Journal of the American Chemical Society.

[53]  A. Listorti,et al.  Photochemistry and Photophysics of Coordination Compounds: Copper , 2007 .

[54]  Pankaj Kumar,et al.  PVC-based membranes of dicyclohexano-24-crown-8 as Cd(II) selective sensor , 2006 .

[55]  M. Licchelli,et al.  What anions do to N-H-containing receptors. , 2006, Accounts of chemical research.

[56]  P. Anzenbacher,et al.  Sensing of antipyretic carboxylates by simple chromogenic calix[4]pyrroles. , 2005, Journal of the American Chemical Society.

[57]  A. P. de Silva,et al.  Fluorescent polymeric AND logic gate with temperature and pH as inputs. , 2004, Journal of the American Chemical Society.

[58]  R. Martínez‐Máñez,et al.  Towards the development of colorimetric probes to discriminate between isomeric dicarboxylates. , 2003, Angewandte Chemie.

[59]  F. Muller‐Karger,et al.  Acetate cycling in the water column of the Cariaco Basin: Seasonal and vertical variability and implication for carbon cycling , 2002 .

[60]  T. Gunnlaugsson,et al.  Fluorescent sensing of pyrophosphate and bis-carboxylates with charge neutral PET chemosensors. , 2002, Organic letters.

[61]  T. Gunnlaugsson,et al.  Lanthanide macrocyclic quinolyl conjugates as luminescent molecular-level devices. , 2001, Journal of the American Chemical Society.

[62]  J. Sessler,et al.  Sapphyrins: versatile anion binding agents. , 2001, Accounts of chemical research.

[63]  Philip A. Gale.  Anion receptor chemistry: highlights from 1999 , 2001 .

[64]  Philip A. Gale,et al.  Anion Recognition and Sensing: The State of the Art and Future Perspectives. , 2001, Angewandte Chemie.

[65]  L. Mu,et al.  The Crystal Structure of Zn(II) Complex of Rhodamine B{Zn(RB)(OAc)2 H2O, RB=9-[2-Ethoxycarbonyl)phenyl]-3,6-bis(ethylamino)-2,7-dimethylxanthylium} : The First Solid Free Radical Species of Rhodamine B Metal Complexes , 2000 .

[66]  Philip A. Gale.  Anion coordination and anion-directed assembly: highlights from 1997 and 1998 , 2000 .

[67]  Thorfinnur Gunnlaugsson,et al.  Luminescent molecular logic gates: the two-input inhibit (INH) function , 2000 .

[68]  E. Anslyn,et al.  Anion recognition: synthetic receptors for anions and their application in sensors. , 1999, Current opinion in chemical biology.

[69]  A. W. Czarnik,et al.  A LONG-WAVELENGTH FLUORESCENT CHEMODOSIMETER SELECTIVE FOR CU(II) ION IN WATER , 1997 .

[70]  F. Schmidtchen,et al.  Artificial Organic Host Molecules for Anions. , 1997, Chemical reviews.

[71]  P. Beer.  Anion selective recognition and optical/electrochemical sensing by novel transition-metal receptor systems , 1996 .

[72]  T. Strasser,et al.  Biocompatible membranes in acute renal failure: prospective case-controlled study , 1994, The Lancet.

[73]  A. Davenport,et al.  Hyperlactataemia and metabolic acidosis during haemofiltration using lactate-buffered fluids. , 1991, Nephron.

[74]  D. F. Eaton,et al.  International Union of Pure and Applied Chemistry Organic Chemistry Division Commission on Photochemistry. Reference materials for fluorescence measurement. , 1988, Journal of photochemistry and photobiology. B, Biology.

[75]  R. Tsien,et al.  A new generation of Ca2+ indicators with greatly improved fluorescence properties. , 1985, The Journal of biological chemistry.

[76]  E. Voigtman,et al.  Reduction of electronic noise in inductively coupled plasma atomic emission and fluorescence spectrometric measurements , 1983 .

[77]  C. Lieber,et al.  Role of acetate in the reduction of plasma free fatty acids produced by ethanol in man. , 1968, Journal of lipid research.

[78]  E. Sandell,et al.  Rhodamine B Equilibria , 1956 .