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3 protocols using 1 8 diazabicycloundec 7 ene

1

Synthesis and Characterization of Liquid Crystal Polymer

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1,5-Pentanedithiol (1,5-PDT; >99%), 1,8-diazabicycloundec-7-ene (DBU), butylatedhydroxytoluene (BHT), and magnesium sulfate (MgSO4; anhydrous powder) were purchased from Sigma-Aldrich and used as received. Hydrochloric acid (HCl), dimethylformamide (DMF), and dichloromethane (DCM) were purchased from Fischer Scientific. The photoinitiator 2,2-dimethoxy-2-phenylacetophenone (DMPA) was purchased from Toronto Research Chemicals. Brilliant Yellow (BY) was purchased from Tokyo Chemical Industry. The liquid crystal monomer, 1,4-bis-[4-(6-acryloyloxy-hexyloxy)benzoyloxy]-2-methylbenzene (RM82; >95%), was purchased from Wilshire Technologies Inc. and used without further purification. Conductive carbon grease, NyoGel 756G, was purchased from Newgate Simms.
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2

Synthesis of PEG-based Nanoparticles and Hydrogels

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For NPs synthesis, polyethylene glycol (PEG, 5 kDa), 1,8-diazabicycloundec-7-ene (DBU), lactic acid (LA), sodium dodecyl sulphate (SDS), and choline chloride (CC) were purchased from Sigma-Aldrich (Darmstadt, Germany) and used as received. For hydrogel synthesis, branched polyacrylic acid carbomer 974P (1MDa, 20% branched degree) was purchased from Fagron (Rotterdam, The Netherlands), phosphate buffered saline solution (PBS), propylene glycol, glycerol, and sodium hydroxide were purchased from Sigma-Aldrich (Germany), whilst agarose was obtained from Invitrogen (Carlsbad, CA, USA); and all were used as received. Rhodamine B base (RhB) (Sb sensitivity < 0.1 mg mL−1, Carlo Erba reagents, Cornaredo, Italy) was used for release experiments.
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3

Asymmetric PBI Derivative Synthesis and Characterization

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The chemical structure of the amphiphilic and asymmetric PBI derivative, (2-(2-methoxyethoxy)ethyl)-9-(tridecan-7-yl) perylene bisimide derivative, (C 42 H 48 N 2 O 6 ; FW: 676.8403) is reported in Fig. 1 (General Synthetic Scheme and Experimental Procedure are described in Supplementary Information). 1-Hexylheptylamine was synthesized following a reported method [39, 40] .
Uric acid (UA), chloroform (HPLC grade, !99.9%), hexamethyldisilazane (purity ! 99%), quartz slides (solid substrates), Roswell Park Memorial Institute (RPMI)-1640, trypsin, L-glutamine, penicillin-streptomycin (pen-strep), Fetal Bovine Serum (FBS), MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenol tetrazolium bromide), dimethyl formamide (DMF), 1,8-diazabicycloundec-7-ene, 1butanol, 1-butyl bromide, dichloromethane, sodium sulfate, HCl, CH 3 CN, methanol, glacial acetic acid, sulfUric acid zinc acetate dihydrate and 2-(2-Aminoethoxy)ethanol were purchased from Sigma-Aldrich. D 2 O (99.96% of D) was purchased from VWR Chemicals. The water used in this work was purified from a Millipore Milli-Q system (18.2 MX cm).
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