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• W2950287736 endingPage "2243" @default.
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• W2950287736 abstract "Methods are described for the synthesis of a series of functionalized derivatives of 9-butyl-1,2,3,4,5,6,7,8-octahydroacridine (9), a building block for several types of highly preorganized host compounds. A key intermediate is 5-benzylidene-9-butyl-2,3,5,6,7,8-hexahydroacridin-4(1H)-one (23), which can also be used in the syntheses of torands and hydrogen-bonding hexagonal lattice receptors. A tridentate cleft (20), consisting of 2,2‘;6‘,2‘‘-terpyridine imbedded in a heptacyclic framework, and a corresponding pentadentate diketone (6) were synthesized from 9 in five and seven steps, respectively. The picrate extraction method was used to estimate the solution stabilities of alkali metal complexes of heptacyclic terpyridyls 6 and 20, which was also compared with a flexible terpyridyl (37). Alkali metal complexes of both heptacyclic terpyridyls showed relatively high Ks values, but low size selectivity. Pentadentate host 6 binds Na+ and K+ more strongly than do most hexadentate crown ethers; flexible tridentate analogue 37 failed to extract alkali metal picrates into chloroform. The complexation abilities of 6 and 20 are attributed to enforced orientation of functional group dipoles toward the center of the molecular cleft. Sodium and potassium picrate complexes of pentadentate cleft 6 were synthesized (1:1 stoichiometry), and a 2:1 complex of calcium triflate (62·Ca(CF3SO3)2) was also prepared." @default.
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• W2950287736 date "1998-03-13" @default.
• W2950287736 modified "2023-10-14" @default.
• W2950287736 title "Molecular Architecture. 2.¹ Synthesis and Metal Complexation of Heptacyclic Terpyridyl Molecular Clefts" @default.
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• W2950287736 doi "https://doi.org/10.1021/jo9720041" @default.
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