Structure determination of liquid molecules by encapsulation in an aromatic cavity with hydrogen bonding and enhanced C–H⋯π interactions

Abstract

Guanidinium−naphthalenedisulfonic acid (GNPS) was used as a molecular catcher because (i) it contains cavity and channel in the network; (ii) the NH2+ can be used as the hydrogen bond donor,...

A new fan-like adaptive porous organic cage for the structure determination of liquid perfume molecules

“…However, the energies of C–H⋯π and C–H⋯O interactions were very low, 53 which might account for the very small chemical shift perturbation as compared to the typical hydrogen bonds. 54 The small chemical shift perturbation by the weak interactions was also consistent with our previous results using guanidinium–naphthalenedisulfonic acid 55 and guanidinium–biphenyldisulfonic acid 56 as the hosts.…”

A box-in-box supramolecular assembly for the highly selective recognition of natural, epigenetically and chemically modified cytosines in water

“…With the Tyndall effect and UV appearance in hand, we tried to use NMR 27,28 to probe the host and guest interactions in solution by detecting the chemical shift changes of protons on both 1 and SC4H. At pH = 7, like the weak non-covalent interactions in GNPS 29 and GBPS, 30 and the electrostatic interactions in a tetraphenylethene system, 31 the chemical shift of the peaks ascribed to 1 (Ha, Hb, Hc, Hd, He, Hf and Hg) showed marginal changes [up-field shifts of 0.02, 0.01, 0.01, 0.04, 0.01, 0.02 and 0.02 ppm (Fig. 4b), respectively.…”

Benchmarking Guanidinium Organosulfonate Hydrogen-Bonded Frameworks for Structure Determination of Encapsulated Guests

“…“molecular chaperones”, − were employed as hosts for the determination of molecular structure, including absolute configuration, for a variety of guest molecules. This method involved adding one of three different adamantoid chaperones (Figure S33) to a neat guest, in liquid form, at room temperature, heating the mixture to achieve a homogeneous solution, followed by cooling with the aim of producing a cocrystal of the adamantoid chaperone and guest. ,, Subsequently, other research groups reported the use of GS frameworks for structure determination of target molecules, , and very recently, a report in this journal described an anthracene-modified adamantoid molecular chaperone for structure determination of guests …”

“…Examples 8S and 24S denote data collected using synchrotron radiation. Examples of the structure determination of 21 other guests (not shown here) using GS hosts have been reported elsewhere. − ,, …”

“…This method involved adding one of three different adamantoid chaperones (Figure S33) to a neat guest, in liquid form, at room temperature, heating the mixture to achieve a homogeneous solution, followed by cooling with the aim of producing a cocrystal of the adamantoid chaperone and guest. 17,19,21 Subsequently, other research groups reported the use of GS frameworks for structure determination of target molecules, 23,24 and very recently, a report in this journal described an anthracene-modified adamantoid molecular chaperone for structure determination of guests. 25 Over the past three decades, our laboratory has reported a substantial number of molecular host frameworks, built from two-dimensional hydrogen-bonded networks of guanidinium (G) and organosulfonate (S) ions (Figure 1), capable of encapsulating a wide range of guests and determining their molecular structure.…”