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  • Molecular recognition of hydrocarbon guests by a supramolecular capsule formed by the 4:4 self-assembly of tris(Zn(2+)-cyclen) and trithiocyanurate in aqueous solution.

Molecular recognition of hydrocarbon guests by a supramolecular capsule formed by the 4:4 self-assembly of tris(Zn(2+)-cyclen) and trithiocyanurate in aqueous solution.

Chemistry, an Asian journal (2012-02-09)
Shin Aoki, Satoshi Suzuki, Masanori Kitamura, Takeharu Haino, Motoo Shiro, Mohd Zulkefeli, Eiichi Kimura
ABSTRACT

We have previously reported that the trimeric Zn(2+)-cyclen complex (tris(Zn(2+)-cyclen), [Zn(3)L(1)](6+)) and the trianion of trithiocyanuric acid (TCA(3-)) assembled in a 4:4 ratio to form a cuboctahedral supramolecular cage, [(Zn(3)L(1))(4)(TCA(3-))(4)](12+) (hereafter referred to as a Zn-cage), in neutral aqueous solution (cyclen=1,4,7,10-tetraazacyclododecane). Herein, we examined the molecular recognition of C(1)-C(12) hydrocarbons (C(n)H((2n+2)) (n≈1-12)), cyclopentane, cyclododecane, cis-decalin, and trans-decalin by the Zn-cage under normal atmospheric pressure. This cage complex was also able to encapsulate guest molecules that had larger volumes than that of the inner cavity of the Zn-cage, thereby suggesting that the inner shape of the Zn-cage was flexible. Computational simulations of Zn-cage-guest complexes provided support for this conclusion. Moreover, the solvent-accessible surface areas (SASA) of the Zn-cage host, guest molecules, and the Zn-cage-guest complexes were calculated and the data were used to explain the order of stability determined by the guest-replacement experiments. The storage of volatile molecules in aqueous solution by the Zn-cage is also discussed.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Decane, SAJ special grade, ≥99.0%
Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, SAJ first grade, ≥98.0%
Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, SAJ special grade, ≥99.0%
Sigma-Aldrich
Decane, anhydrous, ≥99%
Sigma-Aldrich
cis-Decahydronaphthalene, 99%
Sigma-Aldrich
trans-Decahydronaphthalene, 99%
Sigma-Aldrich
Trithiocyanuric acid trisodium salt hydrate, 98%
Supelco
Decane, analytical standard
Sigma-Aldrich
Decane, ≥95%
Sigma-Aldrich
1,3,5-Triazine-2,4,6-trithiol trisodium salt solution, ~15% in H2O, light yellow
Supelco
Decane, analytical standard
Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, anhydrous, ≥99%
Sigma-Aldrich
Trithiocyanuric acid, 95%
Sigma-Aldrich
Cyclen, 97%
Sigma-Aldrich
Decane, ReagentPlus®, ≥99%
Sigma-Aldrich
Decahydronaphthalene, mixture of cis + trans, reagent grade, 98%