Title
Synthesis, fluorescence properties, and conformational analysis of ether-linked (1,8)pyrenophanes
Author
Hajime Maeda, Makoto Geshi, Kenji Hirose, Taniyuki Furuyama, Masahito Segi
Year
2019
Journal
Tetrahedron
Abstract
Mono-, di- and oligo-ether linked (1,8)pyrenophanes 1–7 were synthesized, and their fluorescence and conformational properties in the absence and presence of metal ions were elucidated. Fluorescence spectra of 1.0 × 10−5 M solutions of the mono- and di-ether linked pyrenophanes 1–5 were comprised of only monomer emission bands, while those of the oligoethylene glycol linked analogs 6 and 7 contained both monomer and intramolecular excimer emission bands. Addition of perchlorate salts of Ba2+, Na+ and Li+ to 1:1 v/v CH3CN:CH2Cl2 solutions of 6 and 7 caused decreases in the intensities of the corresponding intramolecular excimer emission bands and, in some cases, increases in the intensities of the monomer emission. Monomer and intramolecular excimer emission from the (1,8)pyrenophanes are suggested to arise from the respective anti and syn conformers, whose ratios are dependent on solvent polarity, temperature and kinds of added metal ions.
Instrument
FP-8500
Keywords
Fluorescence, Ligand binding, Chemical stability, Thermal stability, Organic chemistry, Materials