Synthesis and chemistry of azobenzenes and stilbenes and their application to modification of silica nanoparticles
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1 Synthesis and chemistry of azobenzenes and stilbenes and their application to modification of silica nanoparticles E. Dean Merrill and Zachary J. Butz (mentor: Prof. Ekaterina. Kadnikova) 11th Annual SEARCH Symposium for Research and Creative Achievements UMKC, April 15, This work won the first place in the Physical Sciences, Engineering, and Math Division
2 anoparticle (P) surface modification utilizing click reactions anotechnology has many applications in chemical engineering and more recently has been given attention in the medical field Core-shell hybrid nanoparticles (Ps) can potentially be used to deliver drugs with enhanced specificity or to form biocompatible materials with enhanced properties ur project furthers research in inorganic-organic core-shell Ps We control the attachment of organic monomers to the core for subsequent growth of organic polymers Prof. Ekaterina. Kadnikova,
3 Surface modification of the silica (Ps) Surface of P H Br H 3 C H 3 C CH 3 H CH 3 CH 3 CH 3 CH 3 CH 3 CH a Br The first step was attempted with 3 different solvents: dimethylacetamide (DMA)* methyl ethyl ketone (MEK)* toluene** *Procedure from Daniel A. Savin, Jeffrey Pyun, Gary D. Patterson, et. Al., Journal of Polymer Science: Part B: Polymer Physics, 2002, 40, ** Procedure from Rajesh Ranjan and William J. Brittain, Macromolecules, 2007, 40, Prof. Ekaterina. Kadnikova,
4 IR comparison before and after 3 attachment Attached azide (2100 cm -1 ) sp 3 -C-H bonds on the propyl chain C= of solvent Prof. Ekaterina. Kadnikova,
5 TEM of silica nanoparticles
6 Synthesis of 4,4 -dihydroxyazobenzene 1 H MR H H Synhetic procedure adapted from Wei, W.; Tomohiro, T.; Kodaka, M.; kuno, H., J. rg. Chem. 2000, 65, Prof. Ekaterina. Kadnikova,
7 Synthesis of 4-propargyloxy-4 -hydroxyazobenzene Elemental analysis Element Expected Actual Carbon Hydrogen itrogen Prof. Ekaterina. Kadnikova,
8 Spectroscopy of 4-propargyloxy-4 -hydroxyazobenzene 13 C MR 1 H MR Prof. Ekaterina. Kadnikova,
![Tethering 4-propargyloxy-4 -hydroxyazobenzene to azido-functionalized silica nanoparticles via click chemistry Mechanism for copper(i)-catalyzed [2+3] cycloaddition](/docs-images/78/77669921/images/9-1.jpg "reaction between organic azides and terminal alkynes a.k.a. click reaction Tornøe, C. W.; Morten M. Chem. Rev. 2008, 108, 2952. Prof. Ekaterina.")
9 Tethering 4-propargyloxy-4 -hydroxyazobenzene to azido-functionalized silica nanoparticles via click chemistry Mechanism for copper(i)-catalyzed [2+3] cycloaddition reaction between organic azides and terminal alkynes a.k.a. click reaction Tornøe, C. W.; Morten M. Chem. Rev. 2008, 108, Prof. Ekaterina. Kadnikova,
10 IR evidence of surface functionalization IR spectroscopy reveals a click reaction between the azide group and the propargyl alkyne The evidence is the disappearance of the azide peak at 2100 cm -1 Presence of azide group Absence of azide group Prof. Ekaterina. Kadnikova,
11 UV-vis evidence of surface functionalization UV-vis Azido-functionalized silica P 4-propargyloxy-4'-hydroxyazobenzene Azobenzene-functionalized silica P 0.6 Absorbance Wavelength (nm) UV-vis shows that the azobenzene is attached to the silica nanoparticle Prof. Ekaterina. Kadnikova,
12 Current work and future plans Synthesis of 4-propargyloxy-4 -hydroxystilbene Synthesis of stilbene-functionalized silica nanoparticles H HBr Br 1. Ph 3 P 2. K t Bu 3. Wittig reaction 1. BBr 3 2. H 2 H K 2 C 3 Br H H Prof. Ekaterina. Kadnikova,
13 Current work and future plans Photoisomerization and thermoisomerization of azobenzenes and stilbenes attached to silica nanoparticles Trans 11 lica P h H Cis 11 lica P H Trans 11 lica P h H Cis 11 lica P H Prof. Ekaterina. Kadnikova,
14 Cis-trans isomerization of azobenzenes: model studies Azobenzenes can undergo cis-trans isomerization thermally or photochemically Here are examples of how we can follow this reaction by 1 H MR for a model compound Mixture of cis+trans (~ 1:4) is converted to all-trans by heating at 40 C in the dark solvent Chemical Shift (ppm) Cis and trans (in d 6 -DMS) cis All trans (in d 7 -DMF) cis otice the disappearance of signals from cis-isomer Chemical Shift (ppm) Prof. Ekaterina. Kadnikova,
15 Cis-trans isomerization of azobenzenes: model studies Mixture of cis+trans (~ 1:5) is converted to all-cis by UV light (365 nm) in CD 2 Cl 2 otice the decrease in concentration of trans-isomer and increase in concentration of cis-isomer upon irradiation ormalized Intensity EMD-21-b aromatic Hs for cis 4.68 b 4.68 all cis after 2 minutes of UV light 2.59 a EMD-21-b ormalized Intensity Chemical Shift (ppm) aromatic Hs for trans b b :2 cis to trans after 30 seconds of UV light a a EMD-21-b Chemical Shift (ppm) H a ormalized Intensity b b :5 cis to trans before UV light a a trans H b H b Chemical Shift (ppm) Prof. Ekaterina. Kadnikova,
16 Acknowledgements Prof. Ekaterina. Kadnikova Dr. Alexander Sasha Vorushilov Members of Kadnikova Lab Current and future funding UM Research Board Research Grant to EK ( ) U.S. Army Research ffice (AR CH, ) UMKC SEARCH grant to EDM (2011) Prof. Ekaterina. Kadnikova,
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