Hexyl iodide

Abietic acid (AA ˃ 80%) was supplied by Tokyo Chemical Industry Co. Tetraethylene glycol (TEG ˃ 99%), 1-vinylimidazole (VIM ≥ 99), p-toluene sulfonic acid (PTSA ≥ 99), hydroquinone (≥99), ethyl iodide (EI 99%), hexyl iodide (HI ≥ 98%), toluene (≥99.7), dioxane (≥99), and xylene (≥98.5) were supplied by Sigma-Aldrich Co (Louis, MO, USA). Heavy crude oil was supplied by Aramco Co, Riyadh, Saudi Arabia. Its full specification is reported in our earlier work [18 (link)]. Brine (35,000 ppm) was prepared in our laboratory using distilled water and sodium chloride.

N,N-dimethylacetamide anhydrous 99.8% (DMAc Anh), N,N-dimethylacetamide 99.5% (DMAc), N,N-dimethylformamide 99.5% (DMF), dimethylsulfoxide 99.0% (DMSO), dimethylsulfoxide-d₆ 99.8% (DMSO-d₆), N-methyl-2-pyrrolidinone 99.5% (NMP), 3,5-dinitrobenzoyl chloride 98.0%, 4,4′-oxydianiline 98.0% (ODA), Pd/C (10% w/w), pyridin-4-ylmethanoamine 98.0%, isophthaloyl chloride 98.0%, methyl iodide 98.0%, ethyl iodide 99%, buthyl iodide 99.0%, and hexyl iodide 99% were obtained from Sigma-Aldrich. Ethanol absolute 99.5%, n-hexane 99.5%, diethyl ether 99.5%, tetrahydrofuran 99.5% (THF), lithium bis(trifluoromethanesulfonyl)imide 98.0% (LiTFSI), and hydrazine (80% solution in water) were obtained from Merck. All solvents were purified by distillation under reduced pressure, except for DMAc Anh and DMSO-d₆, which were used directly, as were the liquid reagents. The chlorides used were recrystallized twice from n-hexane, and ODA was sublimated at 300 °C under vacuum (4 × 10⁻⁴ mbar).