Molecular Shuttles Molecular Shuttles Bianca Terminello Chemistry Major Ventura College Andrew Merithew Dr. Luke Theogarajan g j Electrical and Computer Engineering
Big Picture Big Picture • Creating a molecule that uses light energy to drive sodium across a cell membrane • Sodium ions stimulate eye nerve cells • Transfers light energy to chemical energy • Applications in medicine to cure macular degeneration and better renewable energy degeneration, and better renewable energy
The Molecule The Molecule • The molecule is composed of three parts The molecule is composed of three parts Crown Crown Porphyrin Porphyrin Carotenoid Carotenoid Anthraquinone receives negative charge g g receives light receives positive charge g p g
My Research My Research • Centers on the sodium transporter and creating standards of different crown creating standards of different crown anthraquinone to be tested • Forming Carotenoid from the starting Forming Carotenoid from the starting material Crown Porphyrin Carotenoid Anthraquinone
Experimental Methods Experimental Methods • Reactions are set up, and then p, purified using column chromatography g p y • Successful chemical yields are about 60 ‐ 70% about 60 70%. • Crown anthraquinone has low yields yields Milton Beychok
NMR NMR • NMR is short for Nuclear Magnetic Resonance Spectroscopy • An electromagnetic pulse in a magnetic field causes particles to radiate energy ti l t di t back U.S. Department of Energy • This radiated energy • This radiated energy frequency is unique • Can find structure of • Can find structure of material
Overall Chemical Synthesis Overall Chemical Synthesis Retinyl From Starting Materials: Chlorophillin A propionate Trisodium Anthraquinone Anthraquinone Copper Salt Copper Salt Porphyrin Porphyrin + + Carotenoid Carotenoid Crown Porphyrin Carotenoid + Anthraquinone Crown Porphyrin Carotenoid Anthraquinone Final Product
Formation of 18 crown 6 Anthraquinone • 18 refers to the number of atoms in the ring • 6 is the number of Oxygen • Size of the crown selective toward K+ • Standard for comparison
NMR of Crude Reaction Mixture NMR of Crude Reaction Mixture
Chromatography Chromatography • A way to separate out the “other” part of a reaction • Separates based on affinity to mobile phase (liquid) waters.com • Fractions are collected & analyzed by NMR
Reaction 2 Reaction 2 Retinyl From Starting Materials: Chlorophillin A propionate Trisodium • Anthraquinone Anthraquinone Copper Salt Copper Salt Porphyrin Porphyrin + + Carotenoid Carotenoid Crown Porphyrin Carotenoid + Anthraquinone Crown Porphyrin Carotenoid Anthraquinone
Formation of All ‐ trans Retinol Formation of All trans Retinol •The product is all trans retinol •Features mild conditions, safer, selective •Financially advantageous y g
Future research/Summary Future research/Summary • Created standard of crown anthraqunione Created standard of crown anthraqunione • Created starting materials • Continuing research C i i h – Create other standards of the crown anthraquinone h – Couple the molecule – Biological and physical tests
Acknowledgements Acknowledgements I’d like to thank everyone who made this I d like to thank everyone who made this internship possible including: Dr Arica Lubin Dr Jens Uwe Kuhn Dr Nick Dr. Arica Lubin, Dr. Jens ‐ Uwe Kuhn, Dr. Nick Arnold, Dr. Luke Theogarajan, Andrew Merithew Mike Collazo all the other interns Merithew, Mike Collazo, all the other interns, and my friends, family and teachers who made this possible made this possible
Questions? Questions?
Thin Layer Chromatography Thin Layer Chromatography Solvent
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