Dimeric resorcinarene salt capsules with very tight encapsulation of anions and guest molecules

Fangfang Pan,N. Kodiah Beyeh,Kari Rissanen

doi:10.1039/c5ra11905g

Fangfang Pan, N. Kodiah Beyeh + Show 1 more

Open Access

https://doi.org/10.1039/c5ra11905g

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Journal: RSC advances	Publication Date: Jan 1, 2015
Citations: 15	License type: cc-by

Affiliation: Center for NanoScience, University of Jyväskylä

Abstract

The N-cyclohexyl ammonium resorcinarene triflate forms two structurally different capsules with cavity volumes of 341 and 679 Å3 encapsulating either four or eight guest molecules, with very high packing coefficients of 0.74 and 0.67.

Highlights

Crystallization of N-cyclohexyl ammonium resorcinarene triflate from methanol results in a dimeric capsule capable of trapping two triflate anions and two methanol molecules within a 341 A3 cavity while with 1,4-dioxane as a guest it forms a new larger dimeric capsule with volume of 679 A3 encapsulating four 1,4-dioxane and four water molecules, resulting in packing coefficients of 0.75 and 0.67, respectively
While the picrate salt was synthesized from the corresponding cleavage of the tetrabenzoxazine with picric acid, the nitrate and tri ate were obtained through anion exchange of the corresponding chloride salts with silver nitrate and silver tri ate, respectively.[14]
The 1,4-dioxane at the bottom of the cavity is tightly bound from its O-atoms to the host 4(OTf)[4] via one ammonium group and to one water molecule, which is hydrogen bonded to a tri ate anion and to another ammonium group on the other aside of each cavity

Summary

Introduction

Crystallization of N-cyclohexyl ammonium resorcinarene triflate from methanol results in a dimeric capsule capable of trapping two triflate anions and two methanol molecules within a 341 A3 cavity while with 1,4-dioxane as a guest it forms a new larger dimeric capsule with volume of 679 A3 encapsulating four 1,4-dioxane and four water molecules, resulting in packing coefficients of 0.75 and 0.67, respectively. The 1H NMR in DMSO-d6 reveals the salts to be as symmetrical as the corresponding halide analogues NARXs in solution.[11] the effect of the anions which are participating in the intramolecular hydrogen bond seam involving the –NH2 and –OH groups of the resorcinarenes is apparent from the signal changes of the 4(OTf)[4] protons as compared to the 4(Cl)4/4(Br)[4] analogues (Fig. S1†).

Results

Conclusion