Isopropyl alcohol

For the chromatographic analysis, methyl alcohol, n-hexane, isopropyl alcohol, and glacial acetic acid, all of HPLC grade, and water, methyl alcohol, and glacial acetic acid, all of LC-MS grade, were obtained from VWR (Milan, Italy). Analytical- and HPLC-grade water was obtained using purification systems. Phenolic compounds such as (p-hydroxyphenyl) ethanol (p-HPEA) and (3,4-dihydroxyphenyl) ethanol (3,4-DHPEA), vanillic acid, caffeic acid, and α-tocopherol were supplied by Merck (Milan, Italy). The isomer of oleuropein aglycon (3,4-DHPEA-EA), the dialdehydic forms of elenolic acid linked to tyrosol and hydroxytyrosol (p-HPEA-EDA and 3,4-DHPEA-EDA, nowadays named oleconthal and oleacein, respectively), and lignans (+)-1-acetoxypinoresinol and (+)-pinoresinol were extracted from a VOO as reported by Selvaggini et al. [33 (link)]. Pure analytical standards of volatile compounds were purchased from Merck (Milan, Italy).

All reagents were purchased and used without further purification. Ellagic acid (EA) reagent-grade (ACROS Organics, 97%), bismuth (III) acetate (Alfa Aesar, 99%), and glacial acetic acid (Merck, 100%) were used for the synthesis of SU-101. PhACs, used for the adsorption and photodegradation experiments, include atenolol (At; Sigma-Aldrich, ≥ 98%), sulfamethazine (SMT; Sigma-Aldrich, ≥ 99%) and sodium diclofenac (DCF; Sigma-Aldrich, ≥ 98). Formic acid (FA; Thermo Scientific, ≥ 98%) and acetonitrile (ACN; J.T. Baker, HPLC-grade) were used for the preparation of HPLC mobile phases. For the preparation of the phosphate buffered saline (PBS) solution, sodium anhydrous phosphate dibasic (ACROS Organics, 98%), sodium phosphate monobasic anhydrous (ACROS Organics, 98%), orthophosphoric acid (ACROS Organics, ≥ 85%) and Milli-Q water were used. Isopropyl alcohol (VWR, 99%), p-benzoquinone (ACROS, ≥ 98%), disodium ethylenediaminetetraacetate dihydrate (Na₂EDTA, Fisher Scientific, 99.5%) and silver nitrate (ACROS Organics, 99.9%) were employed for active species trapping tests.

Dichloromethane (DCM, 99.9%), isopropyl magnesium chloride lithium chloride complex (iPrMgCl·LiCl, 1.3 M in THF), trimethyl tin chloride (1 M in Hexane, 25 wt.%), acetone and deuterated chloroform (^dCDCl₃) were purchased from Acros Organics (Branchburg, NJ, USA). Hexane, methanol, toluene, hydrochloric acid (HCl), chloroform, acetonitrile and ethyl acetate were purchased from Fisher Scientific (Branchburg, NJ, USA). Ferrocene, tetraethylammonium tetrafluoroborate (Et₄NBF₄) and diethyl ether were obtained from Alfa Aesar (Ward Hill, MA, USA). Anhydrous tetrahydrofuran (THF), n-Butyllithium solution (n-BuLi, 2.5 M in Hexane), Benzo [1,2-b:4,5-b′]dithiophene-4,8-dione, tin(ll) chloride dihydrate, anhydrous sodium sulfate (>99%), indium tin oxide (ITO) glass substrate, 1,3-Bis(5-bromo-2-thienyl)-5,7-bis(2-ethylhexyl)-4H,8H-benzo [1,2-c:4,5-c′]dithiophene-4,8-dione (BDD, 97%), tetrakis(triphenylphosphine) palladium (Pd(PPh₃)₄) and Y6 were purchased from Sigma-Aldrich (Burlington, NJ, USA). Triethyl germanium chloride and 2-iodothiophene were obtained from TCI (Boston, MA, USA). Ethanol was obtained from EMD (Burlington, NJ, USA). Isopropyl alcohol was purchased from VWR (Missouri City, TX, USA). All materials were used as received without further purification.

Ethanol (EtOH) (VWR, 96% GPR RECTAPUR), platinum tetrachloride (PtCl₄) (Sigma Aldrich, 96%), titanium(IV) oxysulfate solution (TiOSO₄) (Sigma Aldrich, 1.9-2.1%), and potassium iodide (KI) (Sigma Aldrich, $⩾$ 99% ACS reagent), Nafion 117 (Sigma Aldrich, 5% in a mixture of lower aliphatic alcohols and water), sulfuric acid (H₂SO₄) (Sigma Aldrich, 96%), isopropyl alcohol (IPA) (VWR, technical), carbon monoxide (CO) (4.7), oxygen (O₂) (5.0), argon (Ar) (5.0), luminol (Sigma Aldrich, $⩾$ 97%), sodium hydroxide (NaOH) (Sigma Aldrich, reagent grade $⩾$ 98%), VULCAN XC-72 carbon black (Cabot Corp.) were used as received from the supplier. Milli-Q water (18.2 MΩ·cm) was used for all experiments.

l-Cysteine (Merck), d-cysteine
(Merck), 1,2-propanediol (Acros Organics), iridium chloride hydrate
(IrCl₃·xH₂O, Merck), cysteamine
(Merck), 3-mercaptopropionic acid (Merck), 37% hydrochloric acid (Fischer
Scientific), ethanol (99.5% purity, Honeywell), acetone (99.5% purity,
Acros Organics), and isopropyl alcohol (99.9% purity IPA, VWR).

NaPSS with an average molecular weight of 70,000, 22-nm-diameter silica nanoparticles [Ludox AS-40 nanoparticle silica; 40% (w/v) suspension in H₂O, pH 9 to 9.5], n-hexadecane (ReagentPlus, ≥99%), toluene, octadecyltrichlorosilane (OTS), sorbitan monooleate (Span 80), and spherical gold (Au) nanoparticles [core radius, ≈2.3 nm; 2% (w/v) suspension in H₂O] functionalized with the capping ligand mercaptoundecyl tetra(ethylene glycol) were obtained from Sigma-Aldrich. The capping ligand is uncharged and provides stability to the colloidal suspension by short-range steric repulsion. COOH-functionalized, multi-walled carbon nanotubes (MWCNTs) with an outer diameter of 30 to 40 nm and a length of 10 to 20 µm were obtained from Arkema. Ethyl acetate (HiPerSolv CHROMANORM, ≥99.8% purity), acetone, ethanol, and isopropyl alcohol (all AnalaR NORMAPUR) were obtained from VWR International. NOA 81 (thiolene-based prepolymer) was obtained from Norland Products, and deionized water was obtained from a Centra ELGA filtration system. All reagents were used as received.