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Updated: May 17, 2026
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Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
Published on: March 12, 2015
Donor-acceptor, ferrocenyl substituted BODIPYs with marvelous supramolecular interactions
Bhausaheb Dhokale1, Prabhat Gautam, Shaikh M Mobin
1Department of Chemistry, Indian Institute of Technology Indore, Indore 452 017, India.
Dalton Transactions (Cambridge, England : 2003)
|November 9, 2012
Summary
New ferrocenyl substituted BODIPY dyes were synthesized. Direct attachment of ferrocene to BODIPY drastically reduced fluorescence, indicating potential for novel electronic materials.
Area of Science:
- Organic Chemistry
- Materials Science
- Supramolecular Chemistry
Background:
- Boron-dipyrromethene (BODIPY) dyes are known for their unique photophysical properties.
- Ferrocene derivatives are widely explored for their redox activity and potential in molecular electronics.
- Combining these moieties can lead to novel functional materials.
Purpose of the Study:
- To design and synthesize novel donor-acceptor ferrocenyl substituted BODIPY compounds.
- To investigate the effect of ferrocene substitution on the photophysical properties of BODIPY.
- To explore the supramolecular assembly and crystal packing of these new compounds.
Main Methods:
- Palladium-catalyzed Suzuki and Sonogashira coupling reactions were employed for synthesis.
- UV-visible absorption spectroscopy was used to study electronic transitions.
- Fluorescence spectroscopy was utilized to determine quantum yields.
- Single crystal X-ray diffraction was performed to analyze crystal structures and intermolecular interactions.
Main Results:
- Successful synthesis of a series of ferrocenyl substituted BODIPYs.
- UV-visible absorption data confirmed intramolecular charge transfer from ferrocene to BODIPY.
- A drastic reduction in fluorescence quantum yield was observed upon direct ferrocene attachment.
- X-ray crystallography revealed diverse supramolecular structures, including 2D networks, sheet-like arrangements, and zigzag packing.
Conclusions:
- Ferrocene substitution significantly influences the electronic and photophysical properties of BODIPY dyes.
- The observed intramolecular charge transfer and fluorescence quenching suggest potential applications in redox-responsive materials.
- The diverse crystal packing highlights the role of supramolecular interactions in dictating solid-state properties.
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