Toluene

The chemicals were purchased from the following sources: Karstedt’s catalyst (platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (Pt₂(dvs)₃) solution in xylene with 2% of Pt), calcium hydride, platinum(IV) oxide (surface area ≥ 75 m²/g) from Sigma-Aldrich (Saint Louis, MO, USA). Sodium and benzophenone from Acros Organics (Geel, Belgium). Polysiloxanes: Cross-linker 101 (PS1, 4.3 mmol/g Si–H content) and 120 (PS2, 1.1 mmol/g Si-H content) from Evonik (Darmstadt, Germany). ((IPr*)Pt(dvds)) (IPr* = 1,3-bis{2,6-bis(diphenylmethyl)-4-methylphenyl}-imidazol-2-ylidene) and Mono(alkenyl)functionalized silsesquioxanes were synthesized according to the literature [101 (link),102 (link)]. Toluene, tetrahydrofuran (THF), chloroform-d, molecular sieves type 4 Å from Chempur (Piekary Śląskie, Poland). Argon and liquid nitrogen were obtained from Linde Gas (Kraków, Poland). All syntheses were conducted under argon atmosphere using standard Schlenk-line and vacuum techniques. Toluene was dried over CaH₂ and THF over Na with benzophenone prior to use and stored under argon over type 4 Å molecular sieves.

The following chemical reagents were used in the procedures described below for the synthesis of KIT-5 materials: Pluronic F127 (ethylene oxide and propylene oxide triblock copolymer EO₁₀₆PO₇₀EO₁₀₆, BASF, Ludwigshafen am Rhein, Germany), tetraethyl orthosilicate, TEOS (≥99%, Sigma-Aldrich, Darmstadt, Germany), 3-mercapropyltrimethoxysilane, MPTMS (95%, abcr GmbH, Karlsruhe, Germany), hydrochloric acid (37.3%, POCh, Gliwice, Poland), ethyl alcohol 96% (POCh, Gliwice, Poland), toluene (Chempur, Piekary Śląskie, Poland), and chloroform (98.5%, POCh, Gliwice, Poland). For the analysis of active acidic centres in the synthesized materials: sodium hydroxide (0.01 M, test portion, Chempur, Piekary Śląskie, Poland), sulphuric acid(VI) (0.005 M, test portion, Merck, Darmstadt, Germany) were used. In the Friedel–Crafts alkylation reaction the following materials were used: anisole (99%, Sigma-Aldrich, Darmstadt, Germany), benzyl alcohol (Ph Eur, Fluka Analytical, Darmstadt, Germany), n-decane (>94%, Merck, Darmstadt, Germany). Commercially available non-mesoporous silica (Sigma-Aldrich, Darmstadt, Germany) was used as a reference material in the heterogeneous catalytic tests, while p-toluenesulfonic acid, PTSA (≥98.5%, Sigma-Aldrich, Darmstadt, Germany) was used as a homogeneous catalyst.

Polished silicon wafers were purchased from ON Semiconductor (Rožnov pod Radhoštěm, Czech Republic). 3-Aminopropyl-trimethoxysilane (APTES), 2-bromoisobutyryl bromide (BriBBr, 98%), ethyl 2-bromo-2-methylpropionate (EBIB, 98%), triethylamine (TEA, >99.5%) tetrahydrofuran (THF, >99.9%), acetone (DMK, >99.9%), tetrabutylammonium perchlorate (TBAP, >98%), and sodium bromide (NaBr, >99%) were purchased from Sigma Aldrich (Saint Louis, MO, USA). Dichloromethane (DCM, >99.5%), toluene (>99.5%), methanol (MeOH, >99.8), ethanol (EtOH, 99.9%), hydrogen peroxide (H₂O₂, 30%), and sulfuric acid (>95%) were purchased from Chempur (Piekary Śląskie, Poland). N,N-Dimethylformamide (DMF, 99.9%) was purchased from Acros (Fair Lawn, NJ, USA). These reagents were used without further purification. Tris(2-pyridylmethyl)amine (TMPA) was synthesized according to a published procedure [61 (link)]. A Cu^IIBr₂/TPMA stock solution was prepared according to reference [62 (link)]. 2-Hydroxyethyl acrylate (HEA; 96%; Aldrich) and tert-butyl acrylate (tBA; >99%; Aldrich) were passed through a column filled with basic alumina prior to use to remove monomethyl ether hydroquinone as an inhibitor. Al wire was purchased from Alfa Aesar (Tewksbury, MA, USA). LDPE cable ties were purchased from LUX-Tools (Wermelskirchen, Germany).