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Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

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FerriCast: a macrocyclic photocage for Fe3+.

Daniel P Kennedy¹, Christopher D Incarvito, Shawn C Burdette

¹Department of Chemisty, University of Connecticut, 55 North Eagleville Road U-3060, Storrs, Connecticut 06269, USA.

Inorganic Chemistry

|January 6, 2010

Summary

A new iron(III) photocage, FerriCast, was synthesized and characterized. Photolysis releases iron, but its interaction with a fluorescent sensor and solvent effects differ from prior studies, highlighting unique selectivity for iron(III) in nonaqueous solvents.

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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

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Area of Science:

Coordination Chemistry
Photochemistry
Supramolecular Chemistry

Background:

Iron(III) is crucial in biological systems, necessitating tools to control its availability.
Photolabile protecting groups (photocages) offer spatiotemporal control over ion release.
Macrocyclic ligands like AT(2)12C4 have been explored for selective metal ion sensing.

Purpose of the Study:

To synthesize and characterize a novel non-siderophoric Fe(3+) photocage, FerriCast.
To investigate the photochemistry and iron(III) release mechanism of FerriCast.
To re-evaluate the coordination chemistry and selectivity of the AT(2)12C4 ligand.

Main Methods:

Synthesis of FerriCast via electrophilic aromatic substitution using TMSOTf.
Spectrophotometric and UV-visible spectroscopy for Fe(3+) binding and release studies.
Evaluation using a turn-on fluorescent sensor and crystallographic analysis of a copper complex.

Main Results:

FerriCast was synthesized in high yield; its Fe(3+) binding is counterion-dependent.
Photolysis at 350 nm converts FerriCast to FerriUnc, reducing Fe(3+) binding affinity.
FerriCast showed no interaction with Fe(3+) in aqueous solution but rapid decomplexation in oxygen-containing solvents, confirming selective Fe(3+) binding in nonaqueous media.

Conclusions:

FerriCast functions as a Fe(3+) photocage, releasing iron upon irradiation.
The AT(2)12C4 ligand exhibits unique selectivity for Fe(3+) in nonaqueous solvents, contradicting previous aqueous studies.
Crystallographic and spectrophotometric data suggest potential redox activity and highlight the need for caution with aniline-containing ligands and redox-active metals.