Guest-dependent complexation of triptycene-based macrotricyclic host with paraquat derivatives and secondary ammonium salts: a chemically controlled complexation process.
The triptycene-based macrotricyclic host containing two dibenzo-[24]-crown-8 moieties has been found to form stable 1:1 or 1:2 complexes in different complexation modes with different functional paraquat derivatives and secondary ammonium salts in solution and in the solid state. Consequently, the alkyl-substituted paraquat derivatives thread the lateral crown cavities of the host to form 1:1 complexes. It was interestingly found that the paraquat derivatives containing two beta-hydroxyethyl or gamma-hydroxypropyl groups form 1:2 complexes, in which two guests thread the central cavity of the host. Other paraquat derivatives containing terminal hydroxy, methoxy, 9-anthracylmethyl, and amide groups were included in the cavity of the host to form 1:1 complexes. Moreover, the host also forms a 1:2 complex with two 9-anthracylmethylbenzylammonium salts, in which the 9-anthracyl groups were selectively positioned outside the lateral crown cavities. The competition complexation process between the host and two different guests (the propyl-substituted paraquat derivative and a dibenzylammonium salt) could be chemically controlled.
Zhao
Jian-Min
JM
Beijing National Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Zong
Qian-Shou
QS
Han
Tao
T
Xiang
Jun-Feng
JF
Chen
Chuan-Feng
CF
D000478:Alkylation; D000577:Amides / Q000737:chemistry; D000873:Anthracenes / Q000138:chemical synthesis*; D001593:Benzyl Compounds / Q000737:chemistry; D043844:Crown Ethers / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010269:Paraquat / Q000031:analogs & derivatives*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
D000577:Amides; D000873:Anthracenes; D001593:Benzyl Compounds; D043844:Crown Ethers; D000644:Quaternary Ammonium Compounds; C071087:dibenzo-24-crown-8; C520712:triptycene; D010269:Paraquat