Facile synthesis of rhodamine-based highly sensitive and fast responsive colorimetric and off-on fluorescent reversible chemosensors for Hg2+: preparation of a fluorescent thin film sensor.

Fluorescence-active chemosensors (L1-L4), comprising a rhodamine scaffold and a pseudo azacrown cation-binding subunit, have been proposed and characterized as a fluorescent chemosensor for Hg(2+). An on-off type fluorescent enhancement was observed by the formation of the ring-opened amide form of the rhodamine moiety, which was induced by the interactions between Hg(2+) and the chemosensor. Upon the addition of Hg(2+), an overall emission change of 350-fold was observed, and the selectivity was calculated to be 300 times higher than Cu(2+) for receptors L2-L4. A polymeric thin film can be obtained by doping poly(methyl methacrylate) or PMMA with chemosensor L2. Such a thin film sensor can be used to detect Hg(2+) with high sensitivity and can be recovered using diluted NaOH.

[1]  Jin-Gou Xu,et al.  Rhodamine thiospirolactone. Highly selective and sensitive reversible sensing of Hg(II). , 2008, Chemical communications.

[2]  J. Vicens,et al.  Novel C3v-symmetrical N7-Hexahomotriazacalix[3]cryptand: a highly efficient receptor for halide anions. , 2006, Organic letters.

[3]  Wei Huang,et al.  Recognition preference of rhodamine-thiospirolactams for mercury(II) in aqueous solution. , 2009, Inorganic chemistry.

[4]  B. Valeur,et al.  Ion-responsive fluorescent compounds. 2. Cation-steered intramolecular charge transfer in a crowned merocyanine , 1989 .

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

[6]  E. Akkaya,et al.  A monostyryl-boradiazaindacene (BODIPY) derivative as colorimetric and fluorescent probe for cyanide ions. , 2008, Organic Letters.

[7]  Kyu‐Sung Jeong,et al.  Molecular receptor for binding quaternary ammonium salts and a large anion effect on the complexation , 1998 .

[8]  Amitava Das,et al.  A rhodamine-based chemosensor that works in the biological system. , 2008, Organic letters.

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

[10]  Ken Kokubo,et al.  Supramolecular triplet photosensitizer. Effects of the cation binding mode on E-Z isomerization of 1,2-dichloroethylene. , 2006, Organic letters.

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

[12]  Yasuhiro Shiraishi,et al.  Rhodamine-based fluorescent thermometer exhibiting selective emission enhancement at a specific temperature range. , 2007, Organic letters.

[13]  N. Chaichit,et al.  Conformation-selective synthesis and binding properties of N-benzylhexahomotriaza-p-chlorocalix[3]trinaphthylamide. , 2008, The Journal of organic chemistry.

[14]  Jiasheng Wu,et al.  Highly sensitive and selective chemosensor for Hg2+ based on the rhodamine fluorophore. , 2007, Organic letters.

[15]  A. Becke.  Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[16]  Fuyou Li,et al.  Multisignaling optical-electrochemical sensor for Hg2+ based on a rhodamine derivative with a ferrocene unit. , 2007, Organic letters.

[17]  J. Tae,et al.  A rhodamine-based fluorescent and colorimetric chemodosimeter for the rapid detection of Hg2+ ions in aqueous media. , 2005, Journal of the American Chemical Society.

[18]  Jin-Gou Xu,et al.  Switching the recognition preference of rhodamine B spirolactam by replacing one atom: design of rhodamine B thiohydrazide for recognition of Hg(II) in aqueous solution. , 2006, Organic letters.

[19]  F. Arnaud-Neu,et al.  A PC compatible computer program for the calculation of equilibrium constants by the simultaneous processing of different sets of experimental results. , 1994, Talanta.

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

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

[22]  Injae Shin,et al.  In vivo monitoring of mercury ions using a rhodamine-based molecular probe. , 2006, Journal of the American Chemical Society.

[23]  Chatthai Kaewtong,et al.  Design and synthesis of thiourea based receptor containing naphthalene as oxalate selective sensor , 2010, Journal of molecular modeling.

[24]  Wei Huang,et al.  Highly sensitive fluorescent probe for selective detection of Hg2+ in DMF aqueous media. , 2007, Inorganic chemistry.

[25]  Jung Hyun Soh,et al.  Rhodamine urea derivatives as fluorescent chemosensors for Hg2 , 2007 .

[26]  Parr,et al.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. , 1988, Physical review. B, Condensed matter.

[27]  Thawatchai Tuntulani,et al.  A reversible Em-FRET rhodamine-based chemosensor for carboxylate anions using a ditopic receptor strategy , 2010 .

[28]  Shuo Wu,et al.  Highly sensitive multiresponsive chemosensor for selective detection of Hg2+ in natural water and different monitoring environments. , 2008, Inorganic chemistry.

[29]  Manoj Kumar,et al.  FRET-induced nanomolar detection of Fe2+ based on cinnamaldehyde-rhodamine derivative , 2011 .

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

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