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Synthesis and Host-Guest Properties of Acyclic Pillar[n]naphthalenes.

ABSTRACT: Here we report a new class of synthetic receptors, acyclic pillar[n]naphthalene (n = 2-4, Dimer, Trimer, and Tetramer) oligomers, which are made up of 2,3-diethoxynaphthalene units linked by methylene bridges at the 1- and 4-positions. They can be synthesized through a one-step condensation of 2,3-diethoxynaphthalene monomer and paraformaldehyde in the presence of BF₃•(Et)₂O catalyst. The crystal structure of Tetramer has an interesting pseudo-cycle shaped structure in the solid state. Their complexation behaviors toward several organic ammonium cations (1 ⁺-15 ⁺) and electron-deficient neutral guests (16-17), were examined by means of ¹H NMR spectroscopy. Tetramer shows good host-guest properties toward the ammonium guests, giving association constants (K _a) in the magnitude of 10²-10⁴ M^-1, which are comparable with those for some macrocyclic hosts.

SUBMITTER: Jia Y

PROVIDER: S-EPMC6901500 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Synthesis and Host-Guest Properties of Acyclic Pillar[n]naphthalenes.

Jia Yuanyin Y Dong Ming M Wang Bin B Li Chunju C

Frontiers in chemistry 20191203

Here we report a new class of synthetic receptors, acyclic pillar[n]naphthalene (n = 2-4, Dimer, Trimer, and Tetramer) oligomers, which are made up of 2,3-diethoxynaphthalene units linked by methylene bridges at the 1- and 4-positions. They can be synthesized through a one-step condensation of 2,3-diethoxynaphthalene monomer and paraformaldehyde in the presence of BF3•(Et)2O catalyst. The crystal structure of Tetramer has an interes ...[more]

PMID: 31850316

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