Guest-Dependent Complexation of Triptycene-Based Macrotricyclic Host with Paraquat Derivatives and Secondary Ammonium Salts: A Chemically Controlled Complexation Process

✍ Scribed by Zhao, Jian-Min; Zong, Qian-Shou; Han, Tao; Xiang, Jun-Feng; Chen, Chuan-Feng

• Book ID: 115524588
• Publisher: American Chemical Society
• Year: 2008
• Tongue: English
• Weight: 377 KB
• Volume: 73
• Category: Article
• ISSN: 0022-3263
• DOI: 10.1021/jo801170t

✦ Synopsis

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 alkylsubstituted 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 β-hydroxyethyl or γ-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.