A fluoride-selective PCT chemosensor based on formation of a static pyrene excimer.

[reaction: see text] Calixarene-based fluorescent chemosensor 1 with two fluorogenic pyrene units conjugated to amide groups as guest recognition sites is synthesized. Complexation of F(-) by 1 causes a red shift of its absorption band to 400 nm (Deltalambda = 54 nm) and a blue shift of the excimer emission to 470 nm (Deltalambda = 12 nm) together with enhanced fluorescence intensity. The blue-shifted excimer emission is attributed to a pyrene dimer formed in the ground state, a so-called static excimer.

[1]  J. Lee,et al.  An excimer-based, binuclear, on-off switchable calix[4]crown chemosensor. , 2004, Journal of the American Chemical Society.

[2]  Jong-In Hong,et al.  A fluorescent pyrophosphate sensor with high selectivity over ATP in water. , 2004, Angewandte Chemie.

[3]  Qi-yu Zheng,et al.  A C-linked peptidocalix[4]arene bearing four dansyl groups: a highly selective fluorescence chemosensor for fluoride ions , 2004 .

[4]  Jong‐In Hong,et al.  An azophenol-based chromogenic pyrophosphate sensor in water. , 2003, Journal of the American Chemical Society.

[5]  M. Ikeda,et al.  A colorimetric and ratiometric fluorescent chemosensor with three emission changes: fluoride ion sensing by a triarylborane- porphyrin conjugate. , 2003, Angewandte Chemie.

[6]  Juyoung Yoon,et al.  Molecular recognition of fluoride anion: benzene-based tripodal imidazolium receptor. , 2003, The Journal of organic chemistry.

[7]  Juyoung Yoon,et al.  A new fluorescent PET chemosensor for fluoride ions. , 2002, Chemical communications.

[8]  Jim-Min Fang,et al.  A novel phosphate chemosensor utilizing anion-induced fluorescence change. , 2002, Organic letters.

[9]  A. Hamilton,et al.  A Dual Channel Fluorescence Chemosensor for Anions Involving Intermolecular Excited State Proton Transfer. , 2001, Angewandte Chemie.

[10]  Jye‐Shane Yang,et al.  Cu2+-induced blue shift of the pyrene excimer emission: a new signal transduction mode of pyrene probes. , 2001, Organic letters.

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

[12]  I. Leray,et al.  Design principles of fluorescent molecular sensors for cation recognition , 2000 .

[13]  S. Ishihara,et al.  A simple anion chemosensor based on a naphthalene–thiouronium dyad , 2000 .

[14]  Philip A. Gale,et al.  Calix[4]pyrroles containing deep cavities and fixed walls. Synthesis, structural studies and anion binding properties of the isomeric products derived from the condensation of p-hydroxyacetophenone and pyrrole. , 1999 .

[15]  Norio Teramae,et al.  Fluorescence Sensing of Anions via Intramolecular Excimer Formation in a Pyrophosphate-Induced Self-Assembly of a Pyrene-Functionalized Guanidinium Receptor , 1999 .

[16]  P. Beer.  Transition-Metal Receptor Systems for the Selective Recognition and Sensing of Anionic Guest Species , 1998 .

[17]  M. Scherer.  A bridged pyrrolic ansa-ferrocene. A new type of anion receptor , 1998 .

[18]  E. C. Lim,et al.  Excimer Formation in van der Waals Dimers and Clusters of Aromatic Molecules , 1996 .

[19]  P. Beer,et al.  Anion recognition properties of new-rim bis[rhenium(I) bipyridyl, ruthenium(II) bis(bipyridyl), cobaltocenium]calix[4]arene receptors dictated by lower-rim substituents , 1996 .

[20]  S. Shinkai,et al.  Selective fluoride recognition with ferroceneboronic acid , 1995 .

[21]  G. Köhler,et al.  Excited state properties and deactivation pathways of 7-aminocoumarins , 1994 .

[22]  Anthony W. Czarnik,et al.  Real-Time Assay of Inorganic Pyrophosphatase Using a High-Affinity Chelation-Enhanced Fluorescence Chemosensor , 1994 .

[23]  F. Winnik.  PHOTOPHYSICS OF PREASSOCIATED PYRENES IN AQUEOUS POLYMER SOLUTIONS AND IN OTHER ORGANIZED MEDIA , 1993 .

[24]  I. Yamazaki,et al.  Transient free-exciton luminescence and exciton—lattice interaction in pyrene crystals , 1987 .

[25]  M. van der Auweraer,et al.  Intramolecular excimer formation in bichromophoric molecules linked by a short flexible chain , 1987 .

[26]  Guilford Jones,et al.  Solvent effects on emission yield and lifetime for coumarin laser dyes. Requirements for a rotatory decay mechanism , 1983 .