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Grubbs first generation catalyst

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Grubbs first-generation catalyst is a ruthenium-based olefin metathesis catalyst. It catalyzes the exchange of alkylidene fragments between two olefins, enabling the formation of new carbon-carbon double bonds.

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Lab products found in correlation

Triisopropylsilane, by Merck Group (2 mentions) Grubbs second generation catalyst, by Merck Group (1 mentions) Diethyl ether, by Avantor (1 mentions) 5 6 carboxyfluorescein, by Merck Group (1 mentions) Anhydrous 1 2 dichloroethane, by Merck Group (1 mentions) Formic acid, by Merck Group (1 mentions) Deuterated solvent, by Merck Group (1 mentions) Trifluoroacetic acid, by Merck Group (1 mentions) Dimethylformamide, by Merck Group (1 mentions) Dichloromethane, by Merck Group (1 mentions) Acetic anhydride, by Merck Group (1 mentions) Rink amide mbha resin, by Merck Group (1 mentions) N n diisopropylethylamine, by Merck Group (1 mentions) Piperidine, by Merck Group (1 mentions) Norbornene, by Merck Group (1 mentions) 5 norbornene 2 methanol, by Merck Group (1 mentions) Benzophenone, by Avantor (1 mentions) Toluene, by Avantor (1 mentions) Allyl alcohol, by Merck Group (1 mentions) 5 norbornene 2 carboxylic acid, by Merck Group (1 mentions)

7 protocols using grubbs first generation catalyst

1

Grubbs Catalyst Polymerization Protocol

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The Grubbs first-generation catalyst [benzylidene-bis(tricyclohexylphosphino)-dichlororuthenium], 1, Grubbs second-generation catalyst [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphino)ruthenium], 2, and other solid reagents and solvents used in this study
were purchased from Sigma-Aldrich and were used without further purification.
Solvents were dried through a small column of activated neutral alumina
(10% v/v) prior to use. All of the preparations were carried out under
Schlenk conditions or in a glovebox.
Swart M.R., Marais C, & Erasmus E. (2021). Comparison of the Spectroscopically Measured Catalyst Transformation and Electrochemical Properties of Grubbs’ First- and Second-Generation Catalysts. ACS Omega, 6(43), 28642-28653.
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2

Fmoc-Amino Acid Solid-Phase Synthesis

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9-Fluorenylmethoxycarbonyl (Fmoc)-protected
amino acids were purchased from CEM (Buckingham, United Kingdom),
Fluorochem (Hadfield, United Kingdom), and Sigma-Aldrich (Gillingham,
United Kingdom), and preloaded Fmoc-Lys(Boc)-Wang resin was from Novabiochem
(Watford, United Kingdom). N,N′-Diisopropylcarbodiimide
(DIC) was from Fluorochem, piperidine, acetic anhydride, triisopropylsilane
(TIS), formic acid, anhydrous 1,2-dichloroethane (DCE), Grubbs first-generation
catalyst, and 5(6)-carboxyfluorescein (FAM) were from Sigma-Aldrich,
and ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma Pure) was obtained
from CEM. Acetonitrile (ACN), dimethylformamide (DMF), dimethyl sulfoxide
(DMSO), and diethyl ether were from VWR (Lutterworth, United Kingdom),
and dichloromethane (DCM) and trifluoroacetic acid (TFA) were obtained
from Fisher Scientific UK (Loughborough, United Kingdom).
Worm D.J., Grabe G.J., de Castro G.V., Rabinovich S., Warm I., Isherwood K., Helaine S, & Barnard A. (2023). Stapled Phd Peptides Inhibit Doc Toxin Induced Growth Arrest in Salmonella. ACS Chemical Biology, 18(12), 2485-2494.
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3

Organic Solvent Preparation and Handling

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All solvents and chemicals
were purchased
from Sigma-Aldrich, Acros Organics, or Fluka and used as received
unless otherwise stated. Triethylamine was distilled from calcium
hydride and stored over molecular sieves (4 Å) under argon prior
to use. Dry solvents were purchased from Acros Organics or Sigma-Aldrich
and stored with a septum and over molecular sieves. Deuterated solvents,
Grubbs first-generation catalyst, Hoveyda–Grubbs first-generation
catalyst, and Pd/C (10 wt %) were purchased from Sigma-Aldrich and
used as received.
Tee H.T., Koynov K., Reichel T, & Wurm F.R. (2019). Noncovalent Hydrogen Bonds Tune the Mechanical Properties of Phosphoester Polyethylene Mimics. ACS Omega, 4(5), 9324-9332.
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4

Synthesis of Modified Amino Acids

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Fmoc-protected
α-amino acids (other than olefinic amino acid Fmoc-(S)-2-amino-2-methyl-hept-6-enoic
acid ((Fmoc-S5-OH)), which was purchased from Sigma-Aldrich) were
purchased from ChemImpex. Rink Amide MBHA resin was purchased from
Sigma-Aldrich. Dimethylformamide (DMF), N,N-diisopropylethylamine (DIEA), acetic anhydride, trifluoroacetic
acid (TFA), dichloromethane (DCM), anisole, 1,2-dichloroethane (DCE),
triisopropylsilane (TIPS), fluorescein isothiocyanate isomer 1 (FITC),
biotin-OSu, and piperidine were purchased from Millipore Sigma and
used as supplied. The Grubbs first-generation catalyst was obtained
from Sigma-Aldrich.
Modi R., McKee N., Zhang N., Alwali A., Nelson S., Lohar A., Ostafe R., Zhang D.D, & Parkinson E.I. (2023). Stapled Peptides as Direct Inhibitors of Nrf2-sMAF Transcription Factors. Journal of Medicinal Chemistry, 66(9), 6184-6192.
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5

Norbornene-based Ring-Opening Polymerization

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Norbornene (99%), 5-Norbornene-2-methanol
(98%, mixture of endo and exo; endo:exo ratio of approximately 60:40 as
revealed by 1H NMR; Figure S1), 2-norbornanemethanol (97%, mixture of endo and exo isomers), first-generation Grubbs catalyst (97%), and
potassium tert-butoxide (reagent grade, ≥98%)
were purchased from Sigma-Aldrich and used as received. Alkoxysilane-modified
G2 catalyst was synthesized as previously reported.19 (link) Solvents (Toluene and THF) were dried by passage through
solvent purification columns and degassed before use. All manipulations
of air- and moisture-sensitive compounds were performed under nitrogen
atmosphere in a glovebox or via standard Schlenk line operations. 1H NMR spectra were recorded on an INOVA 600 (600 MHz) spectrometer.
Baral S., Liu C., Mao X., Coates G.W, & Chen P. (2022). Tuning Single-Polymer Growth via Hydrogen Bonding in Conformational Entanglements. ACS Central Science, 8(8), 1116-1124.
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6

Synthesis of Norbornene-Functionalized PDMS

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PDMS, monohydride terminated
(AB250915, viscosity 5–9 cSt.) (Mn = 1136 g/mol determined by 1H NMR end-group analysis),
was purchased from ABCR. Karstedt’s catalyst (platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane
complex solution in xylene, Pt ≈ 2%), allyl alcohol, 4-(dimethylamino)pyridine
(DMAP), N,N′-diisopropylcarbodiimid
(DIC, 18.4 mL, 122.4 mmol, 3.4 equiv), 5-norbornene-2-carboxylic acid
(mixture of endo and exo, predominantly endo), 5-norbornene-2-carbonitrile, first-generation Grubbs’
catalyst, 2,2-dimethoxy-2-phenylacetophenone (DMPA), and 2,2′-(ethylenedioxy)diethanethiol
(CL) were purchased from Sigma-Aldrich. Poly(vinyl alcohol)
(PVA, R&G-PVA-Folientrennmittel) was purchased from Suter-Kunststoff
AG. Methanol (MeOH), dichloromethane (DCM), ethyl acetate (EA), toluene
(Tol), tetrahydrofuran (THF), and heptane were purchased from VWR.
All chemicals were of reagent grade and used without purification;
only toluene was dried over sodium using benzophenone as an indicator
and DCM over calcium hydride and distilled before use.
Adeli Y., Raman Venkatesan T., Mezzenga R., Nüesch F.A, & Opris D.M. (2024). Synthesis of Bottlebrush Polymers with Spontaneous Self-Assembly for Dielectric Generators. ACS Applied Polymer Materials, 6(9), 4999-5010.
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7

Synthesis of Amphiphilic Brush Polymers

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DEAEMA, 2–bromoisobutyryl bromide, poly(ethylene oxide) (Mn = 2000), CuBr, 4,4′–dinonyl–2,2′–dipyridyl (dNbpy), allyltributyl stannane, and first–generation Grubbs catalyst were purchased from Sigma–Aldrich (St. Louis, MO, USA) and used as received. The poly(ethylene oxide) macroinitiator with 2–bromoisobutyryl terminal groups was prepared through esterification of poly(ethylene oxide) (Mn = 2000) or poly(ethylene glycol) methyl ether (Mn = 2000) with 2–bromoisobutyryl bromide according to a previously reported procedure [16 (link)].
Jiang Y., Zhang T., Yi Z., Han Y., Su X, & Feng Y. (2020). Diblock, Triblock and Cyclic Amphiphilic Copolymers with CO2 Switchability: Effects of Topology. Polymers, 12(4), 984.
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