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13 protocols using decylamine

1

4D Shape-Morphing Material Fabrication

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The photo-cross-linkable ink formulation comprised 30% (w/v) polyethylene glycol diacrylate (PEGDA, Mn = 700, Sigma), 70% deionized (DI) water, and 1% (w/v) photoinitiator Irgacure-819 (Ciba). It was mixed thoroughly by sonification for an hour before DLP printing.
The 4D SMP ink was formulated using bisphenol A diglycidyl ether (monomer), poly(propylene glycol) bis(2-aminopropyl) ether (cross-linker), and decylamine (cross-linking modulator), which were all purchased from Sigma. Graphene nanoplatelets (6–8 nm thick × 5 μm wide) were obtained from Strem Chemicals Inc. The material was added into an open-mouthed container and mixed manually at the weight ratio of 3.4:0.69:0.66 corresponding to monomer:cross-linker:cross-linking modulator (to obtain a transformation temperature of above 37 °C).44 The ink was stored at −80 °C and was placed in a 75 °C oven for 5 min before use to both defrost the solution and lower its viscosity. For the fabrication of 4D material, the ink was extruded at room temperature and then defoamed in a vacuum chamber for 2 h. After this, the printed 4D material was cured in an oven at 100 °C for at least 1 h.
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2

Synthesis of Quantum Dot Nanoparticles

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Wurtzite CdSe/CdZnS core/shell quantum dots and MA-PIL ligands were synthesized as described previously [20 ], PEG side-chains were incorporated using poly(ethylene glycol) methyl ether methacrylate 500 from Sigma–Aldrich. Bio-Beads S-X1 GPC medium was obtained from Bio-Rad Laboratories. Toluene-d8 (D, 99.5%) was obtained from Cambridge Isotope Laboratories. Decylamine (95%) was purchased from Sigma Aldrich. Oleylamine (80–90%) and Bis(trimethylsilyl) sulfide ((TMS)2S; 95%) were purchased from Acros Organics. Rhodamine 590 chloride (R590, MW 464.98) was obtained from Exciton. Toluene (99.5%) and Tetrahydrofuran (THF, 99%) were purchased from Mallinckrodt Chemicals. Ethanol (200 proof) was obtained from Decon Laboratories. Acetone (99.9%) was purchased from VWR. Methanol (99.9%) was purchased from Fisher Scientific. Toluene was dried with activated 4A molecular sieves. THF was dried using the Puresolv system from Innovative Technologies. Synthetic or analytical procedures under inert conditions were carried out using Schlenk line techniques or in a glovebox under N2 atmosphere. All media components were from Sigma Aldrich. 96 well plates with clear plastic bottoms and black walls were obtained from VWR. Calcein AM was obtained from Invitrogen.
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3

Synthesis and Characterization of (DA)2MnCl4 Crystalline Powders

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Decylamine (≥99.0% purity) and hydrochloric acid (HCl, 37 wt %) were purchased from Sigma Aldrich and used without further purification. Decylammonium chloride (C10H21NH3Cl, (DA)Cl) was first synthesized by adding HCl (550 μL, 6.6 mmol) into a solution of Decylamine (1.1 mL, 5.5 mmol) in ca. 5 mL ethanol in an ice water bath with stirring. After evaporating the solvent under reduced pressure, the resulting white powder of (DA)Cl was washed with diethyl ether and dried under vacuum at room temperature for 1 day. Crystalline powders of (DA)2MnCl4 were prepared in a similar manner to previously reported syntheses26 ,44 (link). Specifically, (DA)Cl (96.9 mg, 0.5 mmol) was first dissolved in 4.0 mL of ethanol. After several minutes of stirring, MnCl2·4H2O (49.5 mg, 0.25 mmol) was added to the solution, and the solution was heated to 65 °C. Pale-pink crystals were obtained upon cooling the resulting solution to room temperature at a rate of 4 K h−1. The crystals were filtered, washed with diethyl ether (5 × 10 mL), and dried under vacuum for 6 h to afford 45.2 mg (35.2% yield) of product. Single crystals suitable for X-ray structure determination were obtained by cooling at a rate of 2 K h−1.
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4

Photocurable Hydrogel Synthesis

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Poly(ethylene glycol) diacrylate (PEGDA, MW=700 Da), butanediol diacrylate (BDDA), decylamine, isobutylamine, benzylamine, 2,4-Dimethoxybenzylamine, diphenyl(2,4,6-trimethylbenzoyl) phosphine oxide (TPO), dimethyl sulfoxide (DMSO) and tetrahydrofuran (THF) were purchased from Sigma-Aldrich. Benzhydrazide and phenylacetic hydrazide were purchased from Alfa Aesar. Dulbecco’s phosphate buffered saline (PBS) was obtained from Corning.
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5

Magnetic Bead Functionalization Protocol

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Superparamagnetic Dynabeads MyOne carboxylic acid (2a = 1 μm, carboxylic acid–functionalized, particle concentration = 10 mg/ml, zeta potential = −60 mV; Thermo Fisher Scientific), 1-ethyl-3-(3-dimethyl aminopropyl) carbodiimide hydrochloride (EDC), N-hydroxysuccinimide (NHS), decane, Pluronic F-127, and decylamine were purchased from Sigma-Aldrich and used as received. Dimethyl sulfoxide (DMSO; ≥99.7%) and ethanol (200 proof) were purchased from Fisher Scientific and used as received. 184 Silicon Elastomer Kit was purchased from Dow Inc. (SYLGARD) and used as received. Oil-based ferrofluids EMG 900 was purchased from Ferrotec.
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6

Synthesis of Colloidal Quantum Dots

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Silver
nitrate (AgNO3, ≥99%),
oleic acid (OA, technical grade, 90%), oleylamine (OlAm, 70%), sulfur
(S, 99.99%), cadmium acetylacetonate (Cd(acac)2, ≥99.9%),
trioctylphosphine (TOP, 90%), tetradecylamine (95%), dodecylamine
(98%), decylamine (95%), octylamine (99%), heptylamine (99%), hexylamine
(99%), and NMF (99%) were purchased from Sigma-Aldrich. KCl (99%),
and ammonium carbonate ((NH4)2CO3, 30%) were purchased from SAMCHUN Chemicals.
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7

Synthesis and Characterization of mPEG-b-PAsp

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β-benzyl-L-aspartate N-carboxyanhydride (BLA-NCA) was obtained from Enlai Biological Technology Company (Chengdu, China). mPEG-NH2 (12000 MW) was purchased from Jenkem Technology Company (Beijing, China). mPEG-b-PAsp was synthesized as mentioned method in the reference (The degree of polymerization of PAsp segment was calculated to be 56 according to 1H-NMR spectrum, Supplementary Material: Fig. S1) 17 (link), 19 (link). AO was purchased from Amresco. N-Methyl pyrrolidone (NMP), ICG and decylamine were obtained from Sigma-Aldrich. DHE was obtained from Wusheng Company (Shanghai, China).
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8

Synthesis of Functionalized Nanoparticles

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Methanol was purchased from Fisher Scientific (Fair Lawn, NJ, USA). Toluene, decylamine (C10:0), dodecylamine (C12:0), and octadecylamine (C18:0) were purchased from Sigma Aldrich (St. Louis, MO, USA). Potassium cyanide (KCN), chlorotrimethylsilane, tetradecylamine (C14:0), hexadecylamine (C16:0), and oleylamine (C18:19) were purchased from Acros Organics (Bridgewater, NJ, USA). The 3-(2-furoyl)quinoline-2-carboxaldehyde (FQCA) and the naphthalene-2,3-dicarboxaldehyde (NDA) were purchased from Molecular Probes (Eugene, OR, USA). Perfluorodecalin (PFD) was purchased from Alfa Aesar (Ward Hill, MA, USA). SU-8 2075 positive epoxy photoresist and SU-8 developer were purchased from MicroChem (Newton, MA, USA). Nano-Strip resist remover was purchased from Cyantek (Fremont, CA, USA). Sylgard 184 silicone elastomer kit was purchased from Dow Corning (Midland, MI, USA).
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9

Facile Synthesis of Polymer Composites

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Dicyclopentadiene (DCPD), 5-ethylidene-2-norbonene (ENB), second-generation Grubbs’ catalyst (GC2), phenylcyclohexane (PCH), allyl chloride, urea, sodium hydroxide (NaOH), hydrochloric acid (HCl), and decylamine were purchased from Sigma-Aldrich and used as received. Tannic acid was obtained from Alfa Aesar and used without modification. Tributyl phosphite inhibitor (TBP) was purchased from TCI-Sejin CI. Acetone (99.5%) was purchased from Dae Jung Chemical and used without further purification. Cellulose nanocrystal (CNC) was acquired from Nanografi Nano Technology and used as received. A 26V-65W FX-8801 HAKO soldering iron was used to trigger FP. ISTEK Multimeter CP-500L was used to adjust pH levels. 15 × 150 mm glass test tubes (Tube 2, 15150) were purchased from Dai Han Scientific. 1.5 × 80 mm Borokapillaren capillary tubes were purchased from Muller GmbH. T-type welded thermocouples were purchased from Omega Engineering. TM947SD digital thermometer from Lutron Instruments was used to record temperature values during the FP reaction.
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10

Tailored Biomaterial Synthesis Protocol

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1,4-Butanediol diacrylate (B4), 1,6-hexanediol diacrylate (B6), 1-(3-aminopropyl)-4-methylpiperazine (E7) (Alfa Aesar), octylamine (S8m), decylamine (S10m), acetone, dimethyl sulfoxide (DMSO), dimethylformamide (DMF), tetrahydrofuran (THF), hexane, citric acid monohydrate, disodium phosphate (Sigma-Aldrich, St. Louis, MO, USA), methoxy poly(ethylene glycol) thiol (2 kDa and 800 Da) (Laysan Bio, Inc.), and Verteporfin (VP (US Pharmacopeial Convention, Inc.) were purchased and used as received.
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