Sensors for detecting metal ions and protons based on new green fluorescent poly(amidoamine) dendrimers peripherally modified with 1,8-naphthalimides

Abstract Two recently synthesized poly(amidoamine) dendrimers from zero and second generation whose periphery comprises fluorescent 4-piperidino-1,8-naphthalimide units have been investigated as potential sensors of metal cations and protons. The photophysical characteristics of the dendrimers have been determined by fluorescence and absorption spectroscopy. Experiments have been performed in the presence of Zn 2+ , Ni 2+ , Ce 3+ , Cu 2+ , Co 2+ and Ag + cations. The increase in the fluorescence intensity of the dendrimers in the presence of protons indicates their sensitivity to the protons. The response of the dendrimers ligands depends on the nature of the added metal cations. The best performance is accomplished for detecting Cu 2+ and Co 2+ cations. The results obtained reveal the capacities of these systems to act as reliable detectors of environment pollution by metal cations and protons.

[1]  V. Balzani,et al.  Coordination of Co2+ Ions in the Interior of Poly(propylene amine) Dendrimers Containing Fluorescent Dansyl Units in the Periphery , 2000 .

[2]  J. Chovelon,et al.  Synthesis, photophysical and photochemical properties of fluorescent poly(amidoamine) dendrimers , 2003 .

[3]  X. Qian,et al.  THE SYNTHESIS, APPLICATION AND PREDICTION OF STOKES SHIFT IN FLUORESCENT DYES DERIVED FROM 1,8-NAPHTHALIC ANHYDRIDE , 1989 .

[4]  V. Bojinov,et al.  Synthesis and characterisation of fluorescent polyacrylonitrile copolymers with 1,8-naphthalimide side chains , 2000 .

[5]  P. Meallier,et al.  Photochemistry of Some 1,8-naphthalic Anhydride Derivatives , 1997 .

[6]  I. Grabchev,et al.  Copolymerization and photostabilization of methylmethacrylate with 1,8-naphthalimide fluorescent brighteners , 2001 .

[7]  X. Qian,et al.  Synthesis and photophysical properties of 1,8-naphthalimide-labelled PAMAM as PET sensors of protons and of transition metal ions , 2002 .

[8]  Lajos P. Balogh,et al.  Poly(Amidoamine) Dendrimer-Templated Nanocomposites. 1. Synthesis of Zerovalent Copper Nanoclusters , 1998 .

[9]  James R. Dewald,et al.  A New Class of Polymers: Starburst-Dendritic Macromolecules , 1985 .

[10]  M. Politi,et al.  Intramolecular excimer formation from 1,8-N-alkyldinaphthalimides , 1995 .

[11]  J. Chovelon,et al.  A polyamidoamine dendrimer with peripheral 1,8-naphthalimide groups capable of acting as a PET fluorescent sensor for metal cations , 2003 .

[12]  T. Majima,et al.  Synthesis of ODNs containing 4-methylamino-1,8-naphthalimide as a fluorescence probe in DNA. , 2002, Bioorganic & medicinal chemistry letters.

[13]  J. Olmsted.  Calorimetric determinations of absolute fluorescence quantum yields , 1979 .

[14]  V. Bojinov,et al.  SYNTHESIS OF POLYMERIZABLE 1,8-NAPHTHALIMIDE DYES CONTAINING HINDERED AMINE FRAGMENT , 2002 .

[15]  K. Rurack,et al.  Flipping the light switch 'on'--the design of sensor molecules that show cation-induced fluorescence enhancement with heavy and transition metal ions. , 2001, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[16]  W. Goddard,et al.  Poly(amidoamine) Dendrimers: A New Class of High Capacity Chelating Agents for Cu(II) Ions , 1999 .

[17]  M. Schuster,et al.  Selective separation and recovery of heavy metal ions using water-soluble N-benzoylthiourea modified PAMAM polymers , 2003 .

[18]  K. Koyama,et al.  Nanoscale solution structure and transfer capacity of amphiphilic Poly(amidoamine) dendrimers having water and polar guest molecules inside , 2003 .

[19]  V. Bojinov,et al.  Synthesis and Photophysical Investigations of Novel Polymerizable Blue Emitting Fluorophores – Combination of a Hindered Amine with a Benzo[de]isoquinoline-1,3-dione , 2004 .

[20]  V. Bojinov,et al.  Poly(amidoamine) dendrimers peripherally modified with 1,8-naphthalimides. Photodegradation and photostabilization on polyamide matrix , 2004 .

[21]  V. Balzani,et al.  Dendrimers as luminescent hosts for metal cations and organic molecules , 2003 .

[22]  C. Saudan,et al.  Luminescent dendrimers. Recent advances. , 2003, Topics in current chemistry.

[23]  Terence E. Rice,et al.  Signaling Recognition Events with Fluorescent Sensors and Switches. , 1997, Chemical reviews.

[24]  J. Chovelon,et al.  Poly(amidoamine) dendrimers peripherally modified with 4-ethylamino-1,8-naphthalimide. Synthesis and photophysical properties , 2003 .

[25]  M. Refat,et al.  Charge-transfer interaction of iodine with some polyamidoamines. , 2005, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[26]  J. Soumillion,et al.  Poly(amidoamine) dendrimer peripherally modified with 4-N,N-dimethylaminoethyleneamino-1,8-naphthalimide as a sensor of metal cations and protons , 2004, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[27]  Vincenzo Balzani,et al.  Light-harvesting dendrimers: efficient intra- and intermolecular energy-transfer processes in a species containing 65 chromophoric groups of four different types. , 2002, Angewandte Chemie.

[28]  P. Meallier,et al.  THE SYNTHESIS OF SOME 1,8-NAPHTHALIC ANHYDRIDE DERIVATIVES AS DYES FOR POLYMERIC MATERIALS , 1993 .

[29]  A. P. Silva,et al.  Newer optical-based molecular devices from older coordination chemistry , 2003 .

[30]  R. Weigand,et al.  Solvent dependence of the inhibition of intramolecular charge-transfer in N-substituted 1,8-naphthalimide derivatives as dye lasers , 1996 .

[31]  Richard M. Crooks,et al.  Preparation of Cu Nanoclusters within Dendrimer Templates , 1998 .

[32]  V. Balzani,et al.  Luminescent lanthanide ions hosted in a fluorescent polylysin dendrimer. Antenna-like sensitization of visible and near-infrared emission. , 2002, Journal of the American Chemical Society.

[33]  Steve P. Rannard,et al.  Dendrimers: a new class of nanoscopic containers and delivery devices , 2003 .

[34]  Xin-liang Wang,et al.  The synthesis and spectral properties of novel 4-phenylacetylene-1,8-naphthalimide derivatives , 2005 .

[35]  R. Crooks,et al.  Dendrimer-Encapsulated Metals and Semiconductors: Synthesis, Characterization, and Applications , 2001 .