The Art of Building Small from molecular switches to motors Ben Feringa Stockholm december 8th, 2016 Bioinspired Motion the early days fascinated by… …but no copy or mimic! 17th of December 1903 at Kitty Hawk heading for…..? The Art of Building Small Chemical Synthesis Nano Macro Natural Robot Artifical Robot ± 24 nm = ± 2 m 0.000000024 m effect of length scales soft hard Low Reynolds number Brownian motion Biomolecular Machines Ribosome Bio-Nanomotors Rotary Motor protein synthesis transport – muscle function transport-catalysis Bacterial Flagellar Motor Optical Switching propulsion Information Molecular Nanoscience molecular light switch 0 1 Optical Molecular Switch Binary System at the Molecular Level S S 365 nm 435 nm O I Me2N NO2 Me2N NO2 S S (M)-cis (P)-trans Information Storage Non-destructive read-out Left (0) Right (1) Potential of Molecular Nanotechnology Molecular Electronics Storage capacity of one CD: 1.125.000.000 MB = > 240 years of music Challenges from Molecules to Dynamic Molecular Systems Responsive Materials out of Equilibrium Self-assembly ? Smart Drugs Trigger & Response ? Motion ? Soft Robotics Cell MEMBRANE Self-Assembly amphiphile O O O HO O S S HO O O O O Polar Headgroup Aromatic Core Apolar Tail S Molecular switch R photo- and electro-chemical switching R S Nanotube by self-assembly 100 nm Controlling the disassembly of a Nanotube with light Nano-channel: trigger & response open & close with light ?? Mechanosensitive Channel from E. coli bacterium 3-4 Nm channel in open state Molecular Device MscL channel protein Liposome O2N UV nm) (366 O N O NO2 Vis (>460 nm) N O R O O R O Switch Controlled drug delivery Self-healing materials Smart Pharmaceuticals 0 1 (off) (on) inactive Target Switching a medicine on with a light signal High precision in therapeutic action Bacterial Resistance Cancer Treatment one of humanity’s chemotherapy “ticking time-bombs” http://www.who.int/mediacentre/factsheets/fs194/en/ http://www.who.int/cancer/en/ Photocontrolled Antibiotic O OH OH O O N O N N N N O N O 0 1 (off) (on) No resistance build-up Control biofilm formation Photocontrolled Chemotherapeutic Agent Bortezomib O OH On the market (US; 2003) for the H N N B treatment of mantle cell cancer N OH H O and multiple myeloma N Avoiding severe side-effects in chemotherapy © Simon Jarratt/Corbis Photopharmacology 0 1 (off) (on) Triggering activation with non-invasive light signal Response Target Spatio-temporal precision in action Smart Pharmaceuticals Challenges: near-infrared light imaging > drug activation From Switches to Motors Molecular Motor Meeq Meax > 280 nm Meax Meeq stable (P,P)-trans unstable (M,M)-cis Meax Meeq > 280 nm 1977 Meeq 2006 Meax unstable (M,M)-trans (PhD thesis, p 61) stable (P,P)-cis Unidirectional First electric car 1999 First synthesis of molecular motor `to Stockholm Unidirectional Overcrowded alkene controlled 2016 molecular motor liquid crystals 1991 2005 2011 Chiroptical Unidirectional Molecular nanocar Overcrowded alkene Motor on a Powered translational switch surface motor on surface Man’s Motor vs. Nature’s Motor Motor ATP - ase Molecular Motor How to control rotary motion? in the nanoworld How to control left or right? My Teachers and Hero’s Jacobus van ‘t Hoff Hans Wijnberg Stereochemistry mirror image symmetry “a signature of life” Mirror Image Breaking Symmetry Unidirectional Rotary Molecular Motor Powered by Light DEFINITION: A rotary motor is a device that is able to convert energy input into controlled, directional, rotary motion in a continuous fashion REQUIREMENTS: Controlled Motion Consumption of Energy Directional Movement Repetitive (Continuous) Process Size: a power-stroke motor 1 nanometer Molecular Motor powered by light fast slow slow fast Responsive Catalysts dynamic control of chiral space using a molecular motor product R,S R S chirality multitasking organo-catalyst sequence control Second Generation Molecular Motor Molecular Design enhancing the speed from to 1 rotation/hour more than 10 million rotations/sec Control of Motion Molecular dynamics & length scales Mesoscopic surfaces & catalysts micro-objects & droplets Macromolecular Nano polymer helicity single molecule movement Rotation of a micro object Molecular motor 1nm Glass rod, 5 x 28 µm Design of Molecular Motors on Surfaces S Me S O O (CH2)8 (CH2)8 SH SH Target Motor Molecule 30 20 10 0 CD (mdeg) CD -10 hν>280 nm∆ hν365 nm ∆ hν365 nm ∆ hν365 nm ∆ -20 0 2 4 6 8 Responsive Surfaces Molecular Car 0.000000002 meter 2 meter Four-wheel drive Four Wheel Drive Molecular Car Nano Car How to convert rotary motion into translational motion??? Single molecule motion!!! Molecular Car Single Molecule Nano Car on Surface Autonomous Propulsion System Chemical Catalysis Glucose as fuel ? Fantastic Voyage Nano-Swimmer Fuel: sugar Applications: roving sensors delivery systems 100 nm micro-nano-robots Nanorobots, science or science fiction “The best way to predict the future is to invent it.“ Alan Kay The Art of Building Small N programming molecules responsive & adaptive functions motion dynamic systems Perspective Information systems Responsive materials Smart surfaces 0 1 Self-healing materials Delivery systems Precision therapeutics Adaptive catalysts Roving sensors NanoEnergy converters Soft-robotics ....................... Acknowledgment generations students & co-workers, colleagues & staff, collaborators, mol machine comm, family AC Cope Foundation Leonardo da Vinci “Where Nature finishes producing its own species man begins,with the help of Nature, to create an infinity of species” Imagine the unimaginable .