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4 protocols using isoquinoline

1

Synthesis of Porphyrin-based Polyimide

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5,10,15,20-tetrakis-(4’-aminophenyl) iron (III) porphyrin chloride and 5,10,15,20-tetrakis-(4’-aminophenyl) nickel (II) porphyrin (Ni-TAPP) were synthesized according to a previously reported protocol49 . 100 mg of Pyromellitic dianhydride (4.59×10−1 mM) was dissolved in 1.4 mL N-Methyl-2-Pyrrolidone (NMP) at 100 °C. The solution was cooled to room temperature. Then, 180 mg of 5,10,15,20-tetrakis-(4’-aminophenyl) iron (III) porphyrin chloride (2.30×10−1 mM), 3 drops of isoquinoline, and 1.4 g of polyamic acid solution (Poly(Pyromellitic dianhydride-co-4,4′-oxydianiline)) were introduced in sequence under stirring at room temperature. Pyromellitic dianhydride, isoquinoline and polyamic acid solution, 15.0-16.0 wt.% in NMP) were purchased from Sigma Aldrich without any additional purification before use.
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2

Multi-Ingredient Formulation Protocol

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Glycoluril, hydrochloric acid (37%), 1,6-dibromohexane, deuterium oxide (99.9%), deuterium chloride (35%), isoquinoline and chlorocresol (4-chloro-3-methyphenol) were purchased from Sigma-Aldrich. Paraformaldehyde was purchased from AlfaAesar. Phenoxyethanol, zinc oxide BP, lanolin anhydrous and citric acid monohydrate were purchased from the Sydney Essential Oil Company. Cetostearyl alcohol was purchased from Bronson and Jacobs. White soft paraffin was supplied by The University of Sydney Dispensing Laboratory. Sodium phosphate BP was purchased from the Government Store Department. 1,4-dioxane, calcium hydroxide solution and sulfuric acid were purchased from Merck. Arachis oil was purchased from Proteco and oleic acid from Professional Compounding Chemists of Australia. All water was obtained from an SG ultra clear water system. Phosphate buffered saline (PBS) solutions were made using pure water and PBS tablets from Sigma Life Sciences. All other chemicals including: methanol, ethanol and diethyl ether, were of analytical reagent grade.
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3

Vapor-Phase Nicotine Measurement Protocol

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We measured vapor-phase nicotine using a passive diffusion-based sampler containing a filter treated with sodium bisulfate assembled in our laboratory (Jones et al., 2012 ). Filters were extracted with an internal standard (isoquinoline, Sigma-Aldrich, St. Louis, MO, USA) and analyzed using a gas chromatograph with a nitrogen phosphorus detector (GC-FTD, Shimadzu GC-2014, Shimadzu, Columbia, MD, USA). Nicotine was separated using a capillary column (SHRXI-5MS, Shimadzu, Columbia, MD, USA). We collected 10% field blanks and duplicates. Nicotine concentrations in duplicate monitors were similar and were averaged together. The 17% of nicotine values below the LOD of 0.021 μg/mL (equivalent to 0.049 μg/m3 for a 72 hour duration) were replaced with half the batch-specific LOD.
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4

Synthesis of Iridium Complex Catalyst

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Complex precursor [IrCl(COD)(IMes)] (IMes  =  1,3-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene; COD  =  cyclooctadiene)
and co-substrate mtz were synthesized according to published methods (Kelly
et al., 2008; Seefeld et al., 2008). Isoquinoline and methanol-d 4 were
purchased from Sigma-Aldrich and used as supplied. Para-hydrogen (p-H 2 )
was produced with an in-house-designed generator (Cryoworld B.V., the Netherlands) consisting of a 2 L vessel embedded in a liquid nitrogen bath.
Normal hydrogen (purity 5.0) at 40 bar was cooled down to 77 K in the
presence of 100 mL of 4–8 MESH charcoal (Sigma-Aldrich). The resulting
51 % p-H 2 was transferred into an aluminum cylinder (Nitrous Oxides
Systems, Holley Performance Products, USA) (Feng et al., 2012) and connected
to a set-up for gas–liquid reactions (Eshuis et al., 2015), as sketched in Appendix A.
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