Abstract:The affinity of small
molecules for biomolecular cavities is tuned
through a combination of primary and secondary interactions. It has
been challenging to mimic these features in organic synthetic host
molecules, however, where the cavities tend to be highly symmetric
and nonpolar, and less amenable to chemical manipulation. Here, a
host molecule composed of a TREN ligand and cyclotriveratrylene moiety
was investigated. Size-matched polar guests were encapsulated within
the cavity via triple protonation of the… Show more
“…By triply protonating the capsule to generate [3H-L] 3+ , we previously enhanced its affinity for a series of size-matched polar molecules and modulated guest binding with sulfonate counteranions in aprotic organic solvents. 68 To expand its hostguest chemistry, [3H-L] 3+ can be made water-soluble through the judicious choice of counteranions. Here, we report a protonated tren-based hemicryptophane [3H-L][OMs] 3 ( -OMs = methanesulfonate anion) that operates as a 'turn-on' fluorescent probe for selective detection of aqueous fluoride and also as a highly efficient fluoride sorbent when supported on silica gel.…”
It has been a long-standing challenge to develop organic molecular capsules for selective anion binding in water. Here, selective recognition of aqueous fluoride was achieved through triple protonation of a...
“…By triply protonating the capsule to generate [3H-L] 3+ , we previously enhanced its affinity for a series of size-matched polar molecules and modulated guest binding with sulfonate counteranions in aprotic organic solvents. 68 To expand its hostguest chemistry, [3H-L] 3+ can be made water-soluble through the judicious choice of counteranions. Here, we report a protonated tren-based hemicryptophane [3H-L][OMs] 3 ( -OMs = methanesulfonate anion) that operates as a 'turn-on' fluorescent probe for selective detection of aqueous fluoride and also as a highly efficient fluoride sorbent when supported on silica gel.…”
It has been a long-standing challenge to develop organic molecular capsules for selective anion binding in water. Here, selective recognition of aqueous fluoride was achieved through triple protonation of a...
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