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Panchromatic Absorbers Tethered for Bioconjugation or Surface Attachment
Rui Liu1, Jie Rong1, Zhiyuan Wu1
1Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
Molecules (Basel, Switzerland)
|October 14, 2022
Summary
Researchers synthesized novel porphyrin-perylene-monoimide triads for panchromatic absorption. These molecules offer near-infrared fluorescence and straightforward attachment for bioconjugation and surface applications.
Area of Science:
- Organic Chemistry
- Materials Science
- Photochemistry
Background:
- Porphyrins and perylene-monoimides are crucial chromophores in various applications.
- Developing molecules with broad absorption and specific functionalization is essential for advanced materials.
Purpose of the Study:
- To synthesize two novel triad molecules linking perylene-monoimides to a porphyrin core.
- To characterize their photophysical properties, including panchromatic absorption and near-infrared fluorescence.
- To establish a versatile synthetic route for potential bioconjugation and surface attachment.
Main Methods:
- Synthesis of trans-AB-porphyrins via dipyrromethane condensation.
- Functionalization of porphyrins through dibromination and copper-free Sonogashira coupling.
- Attachment of perylene-monoimide units and tethers (alkynoic acid or isophthalate).
Main Results:
- Successful synthesis of two porphyrin-perylene-monoimide triads.
- Achieved panchromatic absorption spanning 350-700 nm.
- Observed near-infrared fluorescence emission at 733 or 743 nm with a quantum yield of approximately 0.2.
Conclusions:
- The developed synthetic strategy provides efficient access to functionalized triads.
- These triads are promising panchromatic absorbers with tunable NIR emission.
- The molecules are well-suited for applications in bioconjugation and surface functionalization.
