Aqueous Self-Assembly of Fp Derivatives: Multifunctional Metal-Carbonyl Nanovesicles (MCsomes)

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1 Aqueous Self-Assembly of Fp Derivatives: Multifunctional Metal-Carbonyl Nanovesicles (MCsomes) 38 th IPR Symposium-May 4 th 2016 Nimer Murshid and Xiaosong Wang Nimer Murshid Department of Chemistry Waterloo Institute for Nanotechnology University of Waterloo, Ontario, Canada 1

2 OUTLINE Overview challenges objectives Targeted molecules Aqueous solution behaviour Aggregation induced properties Conclusions 2

3 Application of Metal-Carbonyl Complexes (MCCs) MCCs are potentially useful for a range of biomedical applications including: CO-delivery Antitumor Bioassay Cell imaging Probes for vibrational based sensing Strong CO stretching vibrations in the region ( cm -1 ) Relatively free of interference from absorbance of water and biomolecules J. Am. Chem. Soc. 2010, 132, ; Inorg. Chem. 2015, 54, ; Angew. Chem. Int. Ed. 2011, 50,

4 Challenges for MCCs Applications!!! Low stability and solubility in aqueous solution Signals is difficult to detect in diluted solution Structure characterization and rational synthesis 4

5 Research Objectives Rational design of MC complexes that can self assemble in water and have: High stability Strong detectable signals in solution Fluorescence Vibrational Can be optically trapped and manipulate 5

6 Target Molecules Synthesized through migration insertion reaction FpC6 FpC3-Bt Lanigan et al. ACS Macro Lett. 2014, 3, Murshid et al. Chem. Eur. J. 2015, 21, Murshid et al. J. Mater. Chem. C, 2016, DOI: /C6TC01222A 6

7 Aqueous Solution Behaviour of Amphiphes Conventional surfactant Hydrophilic Hydrophobic CO-releasing Can self-assemble in water above their critical micelle concentration (CMC) Colloidally unstable upon dilution below CMC J. AM. CHEM. SOC. 2010, 132,

8 Aqueous Solution Behaviour of Fp derivatives Target molecule Hydrophilic part=???? H 2 O dilution D h = 170 nm PDI = 0.02 ζ = mv 154 M 4 M Murshid et al. Chem. Eur. J. 2015, 21, Cao et al. Macromolecules, 2015, 48, Murshid et al. J. Mater. Chem. C, 2016, DOI: /C6TC01222A 8

9 Aqueous Solution Behaviour of Fp derivatives Hydrophobic Non-surface active No detectable CMC Highly integrated structure (stable upon dilution) High colloidal stability for several months Murshid et al. J. Mater. Chem. C, 2016, DOI: /C6TC01222A 9

10 Nanostructure of the MCsome ζ = mv SLS/DLS TEM AFM Cryo-TEM SAXS CV Bilayer nanovesicle (MCsomes) The structure is confirmed as bilayer vesicle with the bithiophene moieties interdigitated and associated within the inner wall and the iron-carbonyl units exposed to water. Water carbonyl interactions (WCI) direct and stabilize the aqueous self-assembly of FpC3-Bt Murshid et al. Chem. Eur. J. 2015, 21, Murshid et al. J. Mater. Chem. C, 2016, DOI: /C6TC01222A 10

11 Aggregation Induced Emission (AIE) RIR Restriction of Intramolecular Rotation In THF In water The RIR of the aggregated bithiophene units within the the interdigitated membrane and the spatially separation from the iron centres resulting in AIE. Murshid et al. J. Mater. Chem. C, 2016, DOI: /C6TC01222A 11

12 Aggregation Induced Emission (AIE) AIE (different conditions) AIE DMSO 90% water CH 3 CN 90% water Different solvent Different ph Different concentration Different temperature Murshid et al. J. Mater. Chem. C, 2016, DOI: /C6TC01222A 12

13 Vibrational Based Sensing Conventional surface enhanced IR absorption (SEIRA) Conventional Surface enhanced Raman scattering (SERS) with AuNPs without AuNPs Tsang et al. Phys. Rev. Lett. 1980, 45, 201 Olivo et al. Angew. Chem. Int. Ed. 2012, 51, Enhancement occurs when the molecules adsorb at the surface of a substrate The metal islands are polarized by the incident photon field The induced dipole in an island generates a local EM field stronger than that for the incident photon Applied Spectroscopy 2004, 58, 324A-338A Osawa, M., Top. Appl. Phys. 2001, 81,

14 Aggregation Enhanced IR Absorption (AEIRA) Traditional surface IR Enhancement: SEIRA External substrates: Au, Ag, Ru, Al 2 O 3, SiC,. Plasmon resonance or/and phonon resonance Developed self IR Enhancement: AEIRA Self-enhancement. No External substrates Zeta potential = mv Local electric field IR absorption intensity of the CO groups enhanced with more than 100-fold 14 Murshid et al. Chem. Eur. J. 2015, 21, Murshid et al. J. Mater. Chem. C, 2016, DOI: /C6TC01222A

15 Laser Trapping Trapping force is directly depends on Refractive index contrast between the particle and the surrounding Particle size RI out RI in Can be trapped Different RI between the particle and the surrounding RI out RI in Laser trapping of nanosize lipid vesicles is challenging Similar interior and exterior environment Thin wall, negligible contribution RI of water : 1.33 RI of Lipids: 1.45 Masuhara et al. Acc Chem Res, 2012, 45, Oddershede et al. Nano Lett., 2011, 11, Harris et al. Anal. Chem., 2003, 75, Choi et al. Soft Matter, 2014, 10,

16 Laser Trapping of the MCsome Same interior and exterior environment Size = 170 nm Membrane thickness 3.5 nm Zeta potential = mv High refractive index: s 3 s 6 s FpC3-Bt vesicles have been successfully optically trapped and manipulated WITHOUT ANY MODIFICATION OR ADDITIVES Murshid et al. J. Mater. Chem. C, 2016, DOI: /C6TC01222A 16

17 CONCLUSION The metal carbonyl complex FpC3-Bt is hydrophobic and non-surface active FpC3-Bt molecules can self assemble in water into nanovesicles (MCsomes) with high integrated structure 17

18 Acknowledgments NSERC and WIN for Funding IPR members My supervisor Prof. Xiaosong Wang Wang s group members Our collaborators (National Chiao Tung University) Prof. Chien Lung Wang Prof. Hiroshi Masuhara Dr. Ken-ichi Yuyama 18

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