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Quantitative SERS Detection of Uric Acid via Formation of Precise Plasmonic Nanojunctions within Aggregates of Gold Nanoparticles and Cucurbit[n]uril

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Detection of isomeric microscopic host-guest complexes. A time-evolving cucurbit[7]uril complex.

Mohammad Hossein Tootoonchi¹, Song Yi, Angel E Kaifer

¹Center for Supramolecular Science and Department of Chemistry, University of Miami, Coral Gables, Florida 33124-0431, USA.

Journal of the American Chemical Society

|June 26, 2013

Summary

Cucurbit[7]uril forms inclusion complexes with a guest molecule. Initially a mix of isomers, the system shifts over time to favor the adamantyl-included complex.

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Area of Science:

Supramolecular Chemistry
Host-Guest Chemistry
Physical Organic Chemistry

Background:

Cucurbit[n]urils (CBs) are macrocyclic hosts known for their ability to bind various guests.
Ferrocene and adamantane moieties are frequently used in supramolecular chemistry due to their unique properties.
Understanding the dynamics of complex formation is crucial for designing functional supramolecular systems.

Purpose of the Study:

To investigate the kinetic and thermodynamic aspects of inclusion complex formation between cucurbit[7]uril and a specific cationic guest.
To characterize the initial and final states of the complexation process.
To determine the factors influencing the stability of different isomeric complexes.

Main Methods:

Nuclear Magnetic Resonance (NMR) spectroscopy was used to monitor the complexation process over time.

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Isothermal Titration Calorimetry (ITC) was employed to determine binding affinities and thermodynamic parameters.

Computational modeling was utilized to understand the structural preferences of the complexes.

Main Results:

The initial complexation of cucurbit[7]uril with the ferrocenylmethyl-adamantyl ammonium guest yielded an approximately 1:1 mixture of two isomeric complexes.
Over time, the system evolved towards a thermodynamically stable state.
The stable state was predominantly composed of the complex where the adamantyl group was included within the cucurbit[7]uril cavity.

Conclusions:

The formation of cucurbit[7]uril inclusion complexes is a dynamic process influenced by thermodynamic stability.
Isomerization occurs post-complexation, favoring the more stable adamantyl-included isomer.
This study highlights the importance of considering kinetic versus thermodynamic control in supramolecular chemistry.