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1 SUPPORTING INFORMATION Dual Stimuli-Responsive, Rechargeable Micropumps via Host-Guest Interactions ** Debabrata Patra, Hua Zhang, Samudra Sengupta, Ayusman Sen * Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA These authors contributed equally asen@psu.edu UV-Vis Spectrum of trans-azobenzene soaked gel A piece of host gel was cut and soaked in an aqueous solution of trans-azobenzene for 1-2 days. Then, the gel was dialyzed for 5 days to remove any excess azobenzene. To measure spectrum, a small piece of gel (approx. 1 cm 3 ) was placed between two quartz slides and pressed gently to make it flat. The host gel did not show any characteristic adsorption but the host-guest assembled gel showed characteristic absorption of transazobenzene. Figure S1. Absorption spectra of host-guest assembled gel. S1
2 Measurement of concentration of complexed trans-azobenzene by supramolecular substitution: It is difficult to accurately measure the amount of trans-azobenzene complexed inside a gel matrix but we can have a semi-quantitative assessment by the following method. A small piece of host gel (approx. 5 mm 3 ) was soaked in an aqueous solution of transazobenzene for 1-2 days. Then, the gel was dialyzed for 5 days to remove any excess azobenzene. In the next step, the dialyzed gel was incubated with a competing guest (1- adamantylamine hydrochloride; ADA-NH 2 HCl) overnight. The amount of displaced trans-azobenzene was determined by UV-Vis spectroscopy (molar extinction coefficient of azobenzene = 23,200 L.mol -1 cm -1 ) and found to be moles. Figure S2. Absorption spectra of released trans-azobenzene after supramolecular substitution. S2
3 Synthesis of β-cd-peg gel The synthesis of β-cd gel was performed by following a literature reported procedure and the synthesis scheme is shown below. 1 Synthesis of trans-azobenzene guest The synthesis of azobenzene ligand was performed via multistep reactions. Compound A was synthesized following a literature reported procedure. 2 The synthetic scheme is shown below. 1 H-NMR (300 MHz, CDCl 3, ppm) for Compound A: 3.7 (m, 16H); 3.9 (d, 2H); 4.2 (d, 2H); 7.0 (d, 2H, aromatic); 7.5 (m, 3H, aromatic); 7.9 (m, 4H, aromatic). Compound A (3.74 g, 10 mmol) was dissolved in dry dichloromethane (DCM) at 4 C, followed by the addition of triethylamine (2.02 g, 20 mmol). Methylsulfonyl chloride (2.279 g, 15 mmol) was injected drop by drop to the reaction mixture while maintaining the temperature at less than 5 C. After 30 minutes, the reaction mixture was warmed up to room temperature and stirred for another 30 minutes. When the reaction was finally completed (monitored by TLC), the DCM solvent was evaporated. The viscous mixture was again diluted with DCM and was poured into 0.1 M HCl, and the organic layer was washed twice. The organic layer was then poured into a saturated solution of NaHCO 3, reisolated, and the process repeated three times. The organic layer was then separated and added into an aqueous solution saturated with NaCl, reisolated, and the process repeated three times. Afterwards, the organic layer was separated, dried (Na 2 SO 4 ) and concentrated at reduced pressure. The crude product was purified by column chromatography over silica gel (flash) using hexane/ethyl acetate (1:1, 1:4 and 0:1 v/v) as an eluent. Solvent was removed under vacuum and compound B was collected as a colorless oil (Yield: g, 55 %). 1 H-NMR (300 MHz, CDCl 3, ppm) for Compound S3
4 B: 3.05 (s, 3H, -OMs); 3.6 (m, 10H); 3.8 (d, 2H); 4.35 (d, 2H); 4.2 (d, 2H); 7.0 (d, 2H, aromatic); 7.5 (m, 3H, aromatic); 7.9 (m, 4H, aromatic). Compound B (2.26 g, 5 mmol) was added to trimethylamine solution (10 ml) containing 5% ethanol. The reaction mixture was stirred at ~50 o C for 48 h. The crude product was checked by TLC and ethanol was removed at reduced pressure. The light yellow residue was washed with warm hexane under sonication, and further dried under high vacuum. The isolated yield of Compound C was 60 %. 1 H-NMR (300 MHz, CDCl 3, ppm) for Compound C: 2.7 (s, 3H, -OMs); 3.4 (s, 9H; -NMe 3 ); 3.69 (m, 10H); 4.1 (s, broad, 2H, aromatic-o-ch 2 -CH 2 -); 4.2 (d, 2H, aromatic- O-CH 2 -CH 2 -); 7.01 (d, 2H, aromatic); 7.5 (m, 3H, aromatic); 7.9 (m, 4H, aromatic). Synthesis of 4-acrylate-4 -dimethylaminoazobenzene The monomer was synthesized as per literature reported procedure. 3 In a typical procedure, 4-hydroxy-4'-dimethylaminoazobenzene (241 mg) and triethylamine (1.2 equiv., 120 mg) were mixed in 20 ml dichloromethane and cooled in an ice bath. Acryloyl chloride (1.1 equiv., 89 µl) was added slowly to the solution. The reaction was allowed to stir overnight. The organic layer was washed with brine and water and later dried over anhydrous MgSO 4. The crude product was concentrated under vacuum and purified by column chromatography (CH 2 Cl 2 /Methanol: 95/5, R f = 0.5) to yield a brownish-red solid. 1 H-NMR (300 MHz, CDCl 3, ppm): 3.1 (s, 6H); 5.9 (d, 1H); 6.3 (q, 1H); 6.5 (d, 1H); 6.8 (d, 2H); 7.3 (b, 1H); 7.75 (d, 2H); (m, 2H). Mass: (+H). S4
5 Structure of azobenzene gel Functionalization of glass slide The glass surface was functionalized with an adhesion promoter [3- (methacryloxy)propyl] trimethoxysilane by previously reported literature. 4 Pumping velocity on different substrates The Host-Guest gel was placed on two different surfaces (glass and polystyrene) and experiments were performed under identical conditions. The measured velocities of the tracers do not show any significant change. This suggests that the surface charge of the substrate (-60 mv for glass at ph 7.0 and near neutral for polystyrene) does not contribute to the tracers motion. S5
6 Figure S3. Average pumping speed of tracer particles on different surfaces. Tracer velocity during associative complex formation between β-cd and ADA- NH 2 HCl A small piece of β-cd gel was placed inside imaging chamber and sealed tightly by tape. In the next step, solution of ADA.NH 2 HCl and tracer particles was injected into the chamber for observation. In the native form, β-cd contains water in its hydrophobic cavity. After addition of adamantane, β-cd forms host-guest complex and cavity water molecules were replaced by adamantane causing an outward fluid flow near the gel. Figure S4. Tracer velocity with varying concentrations of adamantane. S6
7 List of Videos (videos are 5 times faster): Video S1: β-cdgel soaked with trans-azobenzene_uv on Video S2: β-cdgel soaked with trans-azobenzene_uv on_off_on Video S3: β-cdgel soaked with trans-azobenzene_uv on_top layer Video S4: β-cdgel_uv on Video S5: β-cdgel soaked with trans-azobenzene_100 mm NaCl_UV on Video S6: β-cdgel + trans-azobenzene + tracers: Inclusion Complex Formation Video S7: β-cdgel soaked with trans-azobenzene + ADA-NH 2 : Supramolecular Substitution Video S8: β-cdgel soaked with ADA-NH 2 + trans-azobenzene: No Substitution Video S9: β-cdgel + ADA-NH 2 : Inclusion complex formation Video S10: Azo-gel soaked with α-cd UV on and off Video S11: Azo-coating with α-cd UV on and off Note: For all videos except Video S3, we observed the tracer particles close to the glass surface. References: (1) Cesteros, L. C.; Ramírez, C. A.; Peciña, A.; Katime, I. Poly(ethylene glycol-βcyclodextrin) gels: synthesis and properties. J. Appl. Polym. Sci. 2006, 102, (2) Altomare, A.; Ciardelli, F.; Gallot, B.; Mader, M.; Solaro, R.; Tirelli, N. Synthesis and polymerization of amphiphilic methacrylates containing permanent dipole azobenzene chromophores. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, (3) Zhao, Y.; Tremblay, L.; Zhao, Y. Doubly photoresponsive and water-soluble block copolymers: Synthesis and thermosensitivity. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, (4) Yoon, J.; Bian, P.; Kim, J.; McCarthy, T. J.; Hayward, R. C. Local Switching of Chemical Patterns through Light-Triggered Unfolding of Creased Hydrogel Surfaces. Angew. Chem. Int. Ed. 2012, 51, S7
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