Synthesis of Double-Armed Lariat Ethers with Pyrene Moieties at Each End of Two Sidearms and Their Fluorescence Properties in the Presence of Alkali Metal and Alkaline Earth Metal Cations
- 1 June 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (13), 4403-4411
- https://doi.org/10.1021/jo0498056
Abstract
Two types of double-armed lariat ether derivatives having pyrene moieties at each end of two sidearms, (3x + 1)-crown-x derivatives 1 (x = 5), 2 (x = 6), and 3 (x = 4) (type A) and 3y-crown-y derivatives, 6 (y = 5) and 7 (y = 6) (type B), were synthesized, and their complexation behavior toward alkali metal and alkaline earth metal cations was examined by fluorescence spectroscopy. Pyrene excimer emission decreased accompanied by an increase in monomer emission upon metal ion complexation. This finding is ascribed to the change of the spatial distance of two pyrene rings by movement suppression of both the crown ring and one of the two sidearms based on complexation with the metal cation. The selectivity for alkaline earth metal cations was highly dependent on the fitness of the host cavity and the guest size. Although most of the fluorophores did not respond to alkali metal cations, only trans-7a containing an 18-crown-6 ring showed K(+) selectivity.Keywords
This publication has 27 references indexed in Scilit:
- Fluorescence signaling of transition metal ions: a new approachNew Journal of Chemistry, 2002
- Synthesis and Complexing Ability of a C-Pivot Type of Double-Armed 15-Crown-5 Ethers toward Alkali Metal CationsBulletin of the Chemical Society of Japan, 2002
- Switching of Cation Selectivity toward Na+and K+by a New Type of pH-Responsive 16-Crown-5 in a Countercurrent Double Uphill Transport SystemJournal of the American Chemical Society, 2000
- Double Uphill Transport of Ca2+−Na+ or Ca2+−K+ in Opposite Directions by Lipophilic Crown Ethers with Two Carboxylic Acid MoietiesThe Journal of Organic Chemistry, 1997
- Photophysics of preassociated pyrenes in aqueous polymer solutions and in other organized mediaChemical Reviews, 1993
- Ionic recognition by proton-ionizable lariat ethers and their polymersPublished by Walter de Gruyter GmbH ,1993
- Lariat ethers: from simple sidearms to supramolecular systemsChemical Society Reviews, 1992
- Cellular Magnesium and Na/Mg Exchange in Heart CellsAnnual Review of Physiology, 1991
- C-pivot lariat ethers bearing an electron-donating side arm as lithium cation selective extractantsThe Journal of Organic Chemistry, 1990
- Molecular design of the electron-donating sidearm of lariat ethers: effective coordination of the quinoline moiety in complexation toward alkali-metal cationsJournal of the American Chemical Society, 1988