Calix[6]pyrrole and hybrid calix[n]furan[m]pyrroles (n+m=6): syntheses and host-guest chemistry.
Calix[6]pyrrole 2 and the "hybrid systems" calix[3]furan[3]pyrrole 12, calix[2]furan[4]pyrrole 13, and calix[1]furan[5]pyrrole 14, have been synthesized by increasing conversion of the furan units present in the readily accessible calix[6]furan 3 to pyrroles. The host-guest chemistry of these novel macrocycles towards a number of anions, including halogen ions, dihydrogen phosphate, hydrogen sulfate, nitrate, and cyanide has been investigated in solution by (1)H NMR titration techniques and/or phase transfer experiments. The solid-state structures of the free receptors 2, 12, and 13, the 1:1 complexes of calix[6]pyrrole 2 with chloride and bromide, and the 1:1 complex of 14 with chloride are also reported.
Dipartimento di Chimica Organica e Biologica, Università di Messina, Italy.
Grazia
G
Cafeo
Franz H
FH
Kohnke
Giovanna L
GL
La Torre
Melchiorre F
MF
Parisi
Rosetta
R
Pistone Nascone
Andrew J P
AJ
White
David J
DJ
Williams
D001665:Binding Sites; D047250:Calixarenes; D003486:Cyanides / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D006219:Halogens / Q000737:chemistry; D006860:Hydrogen Bonding; D007477:Ions / Q000737:chemistry*; D046911:Macromolecular Substances; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009566:Nitrates / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D013431:Sulfates / Q000737:chemistry; D017186:Titrimetry
D003486:Cyanides; D005663:Furans; D006219:Halogens; D007477:Ions; D046911:Macromolecular Substances; D009566:Nitrates; D010710:Phosphates; D011166:Porphyrins; D011758:Pyrroles; D013431:Sulfates; C476175:calix(1)furan(5)pyrrole; C476174:calix(3)furan(3)pyrrole; C476173:calix(6)pyrrole; D047250:Calixarenes