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Molecular tweezers using aromatic interactions for binding normally work best in polar instead of nonpolar solvents due to the strong solvophobic effect in the binding. Inspired by biological receptors that utilize “delocalized binding interactions” remote from the binding interface to strengthen guest-binding, we constructed molecular tweezers that have a reversed solvent effect. As the direct aromatic binding interactions were weakened by nonpolar solvent, guest-triggered intrahost interactions between two strategically placed carboxylic acids became stronger and contributed to the binding.
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The molecular recognition unit of a fluorescent sensor is its most cumbersome part to design and synthesize, but is key to the specificity of the sensor. Molecular imprinting within cross-linked micelles using easily synthesized modular templates allowed us to create analyte-specific binding sites with a nearby fluorescent probe. This strategy makes it straightforward to vary the recognition unit independent of the reporting unit, making the sensor potentially applicable to a wide range of molecular analytes.more » « less
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Chemical reactions in a confined nanospace can be very different from those in solution. Imine formation between molecular amines and an aldehyde inside a molecularly imprinted receptor was promoted strongly by the binding. Although how well the amine fit in the binding pocket and its electronic nature both influenced the reaction, the freedom of movement for the amine was the most important factor determining the binding-normalized reactivity.more » « less
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Conformational flexibility in the host's structure is often considered detrimental to its binding. Flexible pseudo-crown ethers with aromatic donor/acceptor groups at the chain ends, however, displayed enhanced binding affinity and selectivity, particularly when the direct binding interactions were compromised by unfavorable solvents.more » « less
