The synthesis and preliminary solution phase ion binding properties of the N-tosylpyrrolidine calix[4]pyrrole 2 are reported. This β-octaalkyl-substituted calix[4]pyrrole, the first to be prepared via a direct condensation reaction, was obtained by reacting the 3,4-alkyl-functionalized pyrrole 8 with acetone in the presence of an acid catalyst. On the basis of (1)H NMR spectroscopic analyses and isothermal titration calorimetry, it was concluded that, compared with the parent, β-unsubstituted calix[4]pyrrole (1), compound 2 possesses significantly enhanced binding ability for halide anions in chloroform. Furthermore, 2 proved capable of solubilizing in chloroform solution the otherwise insoluble salts, CsF and CsCl. These effects are ascribed to the interactions between the four tosyl groups present in 2 and the counter cations of the halide anion salts.
The synthesis and preliminary solution phase ion binding properties of the N-tosylpyrrolidine calix[4]pyrrole 2 are reported. This β-octaalkyl-substituted n class="Chemical">calix[4]pyrrole, the first to be prepared via a direct condensation reaction, was obtained by reacting the 3,4-alkyl-functionalized pyrrole 8 with acetone in the presence of an acid catalyst. On the basis of (1)H NMR spectroscopic analyses and isothermal titration calorimetry, it was concluded that, compared with the parent, β-unsubstituted calix[4]pyrrole (1), compound 2 possesses significantly enhanced binding ability for halide anions in chloroform. Furthermore, 2 proved capable of solubilizing in chloroform solution the otherwise insoluble salts, CsF and CsCl. These effects are ascribed to the interactions between the four tosyl groups present in 2 and the counter cations of the halide anion salts.
Authors: Dae-Wi Yoon; Dustin E Gross; Vincent M Lynch; Jonathan L Sessler; Benjamin P Hay; Chang-Hee Lee Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336
Authors: Jonathan L Sessler; Won-Seob Cho; Dustin E Gross; James A Shriver; Vincent M Lynch; Manuel Marquez Journal: J Org Chem Date: 2005-07-22 Impact factor: 4.354
Authors: Jonathan L Sessler; Dustin E Gross; Won-Seob Cho; Vincent M Lynch; Franz P Schmidtchen; Gareth W Bates; Mark E Light; Philip A Gale Journal: J Am Chem Soc Date: 2006-09-20 Impact factor: 15.419
Authors: Nam Jung Heo; Ju Ho Yang; Vincent M Lynch; Byoung Joon Ko; Jonathan L Sessler; Sung Kuk Kim Journal: Chem Sci Date: 2020-07-24 Impact factor: 9.825