Ethynylferrocene

Manufactured by Merck Group

Ethynylferrocene is a chemical compound consisting of a ferrocene unit with an attached ethynyl group. It is a yellow crystalline solid used as a precursor in organic synthesis and as a reference material in analytical chemistry.

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3 protocols using ethynylferrocene

Synthesis of Graphene-Based Composites

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Tetraethoxysilane (TEOS, 98%), 3-chloropropyltrimethoxysilane (Cl-PTES, 97%), and graphite were purchased from Alfa Aesar (China), and cetyltrimethylammonium bromide (CTAB, 99%) was purchased from Acros (Japan). Acetonitrile (ACN, 99%), dimethylformamide (DMF, 99%), and cyclohexane (99%) were obtained from Merck. (American) Ethynylferrocene (97%), lithium perchlorate (95%), lithium chloride (95%), copper sulfate (99%), sodium diethyldithiocarbamate trihydrate, and HCl (37%) were purchased from Sigma-Aldrich. Sodium nitrate (99%), ascorbic acid (97%), tetrabutylammonium bromide (99%), and poly(vinyl alcohol) (PVA, MW = 72,000 g/mol) originated from Fluka. graphite foils and scotch tape were purchased from Shanghai Carbon Co. Ltd (Shanghai, China). and 3M, respectively. Sodium sulfate anhydrous (99%), manganese sulfate (95%), concentrated sulfuric acid (98%), and aniline (99%) were from Meryer, Kaitong, Kermal, and Macklin, respectively. All compounds were used directly without further purification. The (3-azidopropyl) triethoxysilane (AzPTES) was synthesized with the protocol reported previously [34 (link)].

Wang J., Yang T., Vilà N, & Walcarius A. (2023). Laser Cutting Coupled with Electro-Exfoliation to Prepare Versatile Planar Graphene Electrodes for Energy Storage. International Journal of Molecular Sciences, 24(6), 5599.

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Microwave-Assisted Synthesis of Peptide Therapeutics

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A CEM microwave synthesizer (Liberty Blue) was used for solid phase peptide synthesis of PTs, as previously described [14 (link), 21 (link), 22 (link), 39 (link)]. Fmoc-4-azido-Proline used in the synthesis was prepared as previously reported [21 (link)]. All other Fmoc-, Boc- protected amino acids, N,Nʹ-diisopropylcarbodiimide, ethyl (hydroxyimino) cyanoacetate (OxymaPure) and rink amide resin (100–200 mesh size, 0.53 meq/g substitution) were purchased from Chem-Impex International, INC. Ethynylferrocene and CuI catalyst for the click reaction, and hydrazine, were purchased from Sigma Aldrich. HPLC purifications were performed using a Waters® HPLC system with reverse phase (RP) C18 prep columns. Purity verification of cPTs was carried out by analytical C18 RP-HPLC column, using a BeckmanCoulter® HPLC system. HPLC grade acetonitrile (ACN), Millipore-MilliQ water and 0.1% TFA were used as solvents for the HPLC purification. Mass was confirmed using matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS).

Zhang S., Holmes A.P., Dick A., Rashad A.A., Enríquez Rodríguez L., Canziani G.A., Root M.J, & Chaiken I.M. (2021). Altered Env conformational dynamics as a mechanism of resistance to peptide-triazole HIV-1 inactivators. Retrovirology, 18, 31.

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Synthesis of Azide-Functionalized Silane Precursor

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Tetraethoxysilane (TEOS, 98%), 3-chloropropyltrimethoxysilane (Cl-PTES, 97%) and graphite were purchased from Alfa Aesar and cetyltrimethylammonium bromide (CTAB, 99%) from Acros. Acetonitrile (ACN, 99%), dimethylformamide (DMF, 99%) and cyclohexane (99%) were obtained from Merck. Ethynylferrocene (97%), lithium perchlorate (95%), lithium chloride (95%), copper sulfate (99%), Sodium diethyldithiocarbamate trihydrate, and HCl (37%) were purchased from Sigma-Aldrich. Sodium nitrate (99%), ascorbic acid (97%), tetrabutylammonium bromide (99%) and poly(vinyl alcohol) (PVA, MW = 72000 g/mol) originated from Fluka. All compounds were used directly without further purification.
Preparation of 3-azidopropyltrimethoxysilane (AzPTMS). The AzPTMS precursor was synthesized by adding 2 g of Cl-PTES, 1.08 g sodium azide and 1.29 g tetrabutylammonium bromide) in 100 mL ACN, which was stirred and refluxed at 90 o C for 24 h under nitrogen atmosphere. Then, the ACN solvent was removed by rotary evaporation at 80 o C under a vacuum of 0.2 bar. The residual mixture was suspended in cyclohexane and filtered with filter paper. The residual cyclohexane was further removed by rotary evaporation at 80 o C under pressure of 0.2 bar and the oily Az-PTMS can be finally obtained. Yield: ~1.3 g, 65 %. 1 H NMR (400 MHz, CDCl3): δ (ppm) 3.82 (s, 9H), 3.65 (t, 2H, 8.25 Hz), 1.24 (m, 2H), 0.75 (t, 2H, 8.31 Hz).

Wang J., Vilà N, & Walcarius A. (2020). Redox-Active Vertically Aligned Mesoporous Silica Thin Films as Transparent Surfaces for Energy Storage Applications. ACS applied materials & interfaces, 12(21).

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