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New Fluorenocrownophanes with Naphthalene Fragments: Synthesis, Structure, Properties and Interaction with Paraquat

A. Yu. Lyapunov,a A. V. Lobach,a I. S. Yakovenko,a E. Yu. Kulygina,a S. V. Shishkina,b,c R. I. Zubatyuk,b and T. I. Kirichenkoa@
aA.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, 65080 Odessa, Ukraine
bSSI “Institute for Single Crystals”, National Academy of Sciences of Ukraine, 61001 Kharkiv, Ukraine
cV.N. Karazin Kharkiv National University, 61022 Kharkiv, Ukraine
@Corresponding author E-mail: ti-kirichenko@rambler.ru
 
DOI: 10.6060/mhc150766k
Macroheterocycles 2015 8(4) 394-401
 
New crownophanes containing fragments of 1,5-dioxynaphthalene and 2,7-dioxyfluorene or 2,7-dioxyfluorene were synthesized by reduction of the corresponding fluorenonocrownophanes. H2–Pd/C or Wolff-Kishner methods were utilized. Molecular structure of bis(fluoreno)crownophane with tetraethyleneglycol linkers was confirmed by single-crystal X-ray diffraction. The formation of pseudorotaxane-type host-guest complexes of the obtained crownophanes with paraquat dication was detected by FABMS, 1H NMR and UV-Vis spectroscopy.
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