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Beryllium-based fluorenes as efficient anion sponges.

M Merced Montero-Campillo¹, Inés Corral², Otilia Mó²

¹Instituto de Química Médica, CSIC, C/Juan de la Cierva, 3, 28006 Madrid, Spain. mm.montero@iqm.csic.es.

Physical Chemistry Chemical Physics : PCCP

|August 18, 2017

Summary

New fluorene derivatives act as "anion sponges," exhibiting exceptionally high affinities for various anions. These compounds show potential for anion binding in both gas and aqueous phases, similar to naphthalene analogues.

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Area of Science:

Computational Chemistry
Supramolecular Chemistry
Materials Science

Background:

Understanding molecular recognition is crucial for designing novel materials.
Proton sponges are well-known for their high affinity to protons.
The development of anion-binding molecules is an active area of research.

Purpose of the Study:

To investigate the anion affinities of novel 4,5-bis(BeX)-fluorene derivatives.
To explore the potential of these fluorene derivatives as anion sponges.
To compare the anion-binding capabilities of fluorene and naphthalene frameworks.

Main Methods:

Density Functional Theory (DFT) calculations using the B3LYP functional.
High-level ab initio composite methods (G4MP2) for validation.
Investigation of anion affinities in both gas and aqueous phases.

Main Results:

4,5-bis(BeX)-fluorene derivatives display among the highest reported anion affinities for neutral molecules.
These fluorene derivatives function effectively as anion sponges, comparable to 1,8-diBeX-naphthalene analogues.
Water interaction reduces anion affinities but they remain substantial, with gas-phase trends largely preserved for monoanions.

Conclusions:

Fluorene and naphthalene frameworks, when appropriately substituted, can act as either proton or anion sponges.
The BeX substituents are identified as potent electron acceptors, facilitating strong anion binding.
These findings highlight the potential of designed organic molecules for selective anion recognition and sequestration.