3-(Dicyanomethylidene)indan-1-one-Functionalized Calix[4]arene-Calix[4]pyrrole Hybrid: An Ion-Pair Sensor for Cesium Salts.

A chromogenic calix[4]arene-calix[4]pyrrole hybrid ion pair receptor bearing an indane substituent at a β-pyrrolic position has been prepared. On the basis of solution-phase UV-vis spectroscopic analysis and (1)H NMR spectroscopic studies carried out in 10% methanol in chloroform, receptor 1 is able to bind only cesium ion pairs (e.g., CsF, CsCl, and CsNO3) but not the constituent cesium cation (as its perchlorate salt) or the F(-), Cl(-), or NO3(-) anions (as the tetrabutylammonium salts). It thus displays rudimentary AND logic gate behavior. Receptor 1 shows a colorimetric response to cesium ion pairs under conditions of solid-liquid (nitrobenzene) and liquid-liquid (D2O-nitrobenzene-d5) extraction.

[1]  B. Moyer,et al.  Capture and metathesis-based release of potassium salts by a multitopic ion receptor. , 2013, Chemical communications.

[2]  Mika Rottenberg.  SQUEEZE , 2012, Kunst fördert Wirtschaft.

[3]  B. Moyer,et al.  KF and CsF recognition and extraction by a calix[4]crown-5 strapped calix[4]pyrrole multitopic receptor. , 2012, Journal of the American Chemical Society.

[4]  N. Robertson,et al.  Naphthyl Derivatives Functionalised with Electron Acceptor Units – Synthesis, Electronic Characterisation and DFT Calculations , 2012 .

[5]  L. Delmau,et al.  A calix[4]arene strapped calix[4]pyrrole: an ion-pair receptor displaying three different cesium cation recognition modes. , 2010, Journal of the American Chemical Society.

[6]  Jaeduk Yoo,et al.  Strapped calix[4]pyrroles bearing a 1,3-indanedione at a beta-pyrrolic position: chemodosimeters for the cyanide anion. , 2009, Organic letters.

[7]  P. Anzenbacher,et al.  1,3-indane-based chromogenic calixpyrroles with push-pull chromophores: synthesis and anion sensing. , 2006, Organic letters.

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

[9]  Philip A. Gale,et al.  Calix[4]pyrrole: an old yet new ion-pair receptor. , 2005, Angewandte Chemie.

[10]  C. Brückner,et al.  Synthesis of 5,10-diphenylporphyrin , 2002 .

[11]  S. Bella.  Second-order nonlinear optical properties of transition metal complexes , 2001 .

[12]  J. Sessler,et al.  Calix[4]pyrrole dimers bearing rigid spacers: towards the synthesis of cooperative anion binding agents , 2000 .

[13]  R. Dabestani,et al.  Calix[4]arene-based Cs+ selective optical sensor , 1999 .

[14]  Ian R. Whittall,et al.  Organometallic Complexes in Nonlinear Optics I: Second-Order Nonlinearities , 1998 .

[15]  A. Berinstain,et al.  Tuning the Singlet−Triplet Energy Gap in a Non-Kekulé Series by Designed Structural Variation. The Singlet States of N-Substituted-3,4-dimethylenepyrrole Biradicals , 1997 .