Chemistry Faculty Publications
Document Type
Article
Abstract
The synthesis, structure, and anion binding properties of chromogenic octamethylcalix[4] pyrroles (OMCPs) and their N-confused octamethylcalix[4] pyrrole isomers (NC-OMCPs) containing an inverted pyrrole ring connected via alpha'- and beta-positions are described. X-ray diffraction analyses proved the structures of two synthesized isomeric pairs of OMCPs and NC-OMCPs. The addition of anions to solutions of chromogenic OMCPs and NC-OMCPs resulted in different colors suggesting different anion-binding behaviors. The chromogenic NC-OMCPs showed significantly stronger anion-induced color changes compared to the corresponding chromogenic OMCP, and the absorption spectroscopy titrations indicated that chromogenic OMCPs and NC-OMCPs also possess different anion binding selectivity. Detailed NMR studies revealed that this rather unusual feature stems from a different anion-binding mode in OMCPs and NC-OMCPs, one where the beta-pyrrole C-H of the inverted pyrrole moiety participates in the hydrogen-bonded anion-NC-OMCP complex. Preliminary colorimetric microassays using synthesized chromogenic calixpyrroles embedded in partially hydrophilic polyurethane matrices allow for observation of analyte-specific changes in color when the anions are administered in the form of their aqueous solutions and in the presence of weakly competing anions.
Copyright Statement
Publisher PDF
Repository Citation
Nishiyabu, Ryuhei; Palacios, Manuel A.; Dehaen, Wim; and Anzenbacher, Pavel Jr., "Synthesis, Structure, Anion Binding, And Sensing By Calix[4] Pyrrole Isomers" (2006). Chemistry Faculty Publications. 74.
https://scholarworks.bgsu.edu/chem_pub/74
Publication Date
9-2006
Publication Title
Journal Of The American Chemical Society
DOI
https://doi.org/10.1021/ja0622150
Start Page No.
11496
End Page No.
11504