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6 protocols using 1 butanethiol

1

Synthesis and Characterization of Imprinted Polymers

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HTM (1), l-histidine (HTD, 2), imidazole (IDZ, 3),
and tryptamine (TTM, 4) were purchased from Sigma-Aldrich
and used as received. Methacrylic acid (MAA, 5) and ethylene
glycol dimethacrylate (EGDMA, 6) were purchased from
Sigma-Aldrich and purified by passing through basic alumina (Al2O3) columns. AIBN was obtained from Sigma-Aldrich
and recrystallized in ethanol twice before use. Carbon disulfide and
1-butanethiol (both from Sigma-Aldrich) were used as received. MCEBTTC
(7) was synthesized according to the procedure outlined
below. High-performance liquid chromatography (HPLC)-grade solvents,
such as dimethyl sulfoxide (DMSO) (Sigma-Aldrich), acetonitrile (MeCN)
(Honeywell Burdick & Jackson), and methanol (Fisher Scientific),
were used without further purification. Na2HPO4 (BDH Chemicals), NaH2PO4·2H2O (AJAX Chemicals), KH2PO4 (Sigma-Aldrich),
and H3PO4 (85%) (Sigma-Aldrich) were used as received
(Figure 1).
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2

Radiolabeled Branched PEI Nanoparticle Synthesis

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PEI (Branched, Mw = 25,000), chloramine-T trihydrate (ch-T), HPAO, 1-butanethiol, potassium iodide (KI), acetic anhydride (Ac2O), triethylamine (TEA), phosphate buffered saline (PBS), and 1-ethyl-3-(3-(dimethylamino)propyl) carbodiimide hydrochloride (EDC) were supplied by Sigma-Aldrich (St. Louis, MO). PEG monomethyl ether with one end terminating in a carboxyl group (mPEG-COOH, Mw = 5000), PEG with one end terminating in a maleimide group and the other in a succinimidyl valerate group (MAL-PEG-SVA, Mw = 5000), and cellulose dialysis membranes were obtained from Shanghai Yanyi Biotechnology Corporation (Shanghai, China). CTX peptide was manufactured by Shanghai Bootech BioScience & Technology Co., Ltd. (Shanghai, China). Na131I solution was obtained from Shanghai GMS Pharmaceutical Co., Ltd. (Shanghai, China). Disposable PD-10 desalting columns, fluorescein isothiocyanate (FI), cell counting kit-8 (CCK-8), C6 glioma cells, fetal bovine serum (FBS), RPMI 1640 medium, penicillin, and streptomycin were procured from Shanghai Dobio CO., Ltd. (Shanghai, China). HAuCl4·4H2O, sodium borohydride (NaBH4), and all other chemicals and solvents were supplied by Sinopharm Chemical Reagent Co., Ltd. (Shanghai, China).
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3

Synthesis of Chalcogenide Nanocrystals

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1-Octadecene
(90%), oleic acid (90%), CdO
(≥99.99%), Se powder (100 mesh, 99.99%), trichloroethylene
(anhydrous, ≥ 99%), 1-butanethiol (99%), 1-pentanethiol (98%),
1-hexanethiol (97%), 1-heptanethiol (98%), 1-octanethiol (≥98.5%),
1-nonanethiol (98%), 1-decanethiol (96%), 2-methyl-1-butanethiol (99%),
3-methyl-1-butanethiol (97%), 2-ethyl-1-hexanethiol (97%), 2-methyl-1-hexanoic
acid (98%), 5-methyl-1-hexanoic acid (98%), 4-methyl-1-octanoic acid
(98%), 4-ethyl-1-octanoic acid (98%), 4-methyl-1-nonanoic acid (99%),
LiAlH4, p-toluenesulfonyl chloride (99%),
thiourea (99%), toluene-d8 (99.6% D),
and chloroform-d1 (99.8% D) were purchased
from Sigma-Aldrich, Alfa Aesar, or Acros Organics.
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4

Comprehensive Analysis of Sulfur Compounds

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The studied sulfur compounds: ethanethiol (97%), dimethyl sulfide (99%), 1-propanethiol (99%), thiophene (99%), diethyl sulfide (98%), 1-butanethiol (99%), dimethyl disulfide (99%), ethyl thioacetate (98%), 1-pentanethiol (98%), 2-(methylthio)ethanol (99%), 3-(methylthio)propionaldehyde (96%), dipropyl sulfide (97%), diethyl disulfide (99%), thiophenol (97%), 2-methyltetrahydrothiophene-3-one (97%), 3-thiophenecarboxaldehyde (98%), 3-(methylthio)-1-propanol (98%), 2-thiophenecarboxaldehyde (98%), ethyl 3-(methylthio)propionate (99%), dibutyl sulfide (98%), dipropyl disulfide (98%), and benzothiazole (96%) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Ethanol and sodium chloride were obtained from Chempur (Piekary Slaskie, Poland). EDTA was purchased from Sigma-Aldrich (St. Louis, MO, USA). Distilled water was purified with use of Millipore Simplicity UV purification system (18.2 MΩ·cm, Simplicity Millipore Waters, Milford, MA, USA).
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5

Synthesis of Functional Nanomaterials via RAFT Polymerization

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Poly(ethylene glycol) methyl ether acrylate (PEGA, average Mn = 480 g mol -1 ), n-butyl acrylate (n-BA, >99%) and t-butyl acrylate (t-BA 98%), Bromo-propionic acid (>99%), 1butanethiol (99%), carbon disulphide (>99%) and tannic acid (ACS reagent) were obtained from Sigma-Aldrich. All monomers above were passed through basic aluminium oxide to remove inhibitor before use. Chloroform-d3 (99.8% D atom), was obtained from Sigma Aldrich and used for 1 H NMR spectroscopy. Thermal initiator 4,4′-azobis(4-cyanovaleric acid) (ACVA, >98%, Aldrich), was used as received. Cyanine 7.5 amine was purchased from Lumiprobe. TEM grids were purchased from EM Resolutions Ltd (Sheffield, UK). RAFT agent, 2-(((butylthio)carbonothioyl)thio)propanoic acid (PABTC) was synthesised as previously described. 22
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6

Synthesis of Heterogeneous Catalysts

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All the organic reagents were commercial products of analytical purity and were used without further purication. The silica and carbon based heterogeneous catalysts were obtained from Johnson Matthey (5% Pt/SiO 2 Batch M04483, JM ref.
108070; 5% Ru/SiO 2 Batch M04484, JM ref. 108070; 5% Ru/C Batch M02070, JM ref. 94890). The 5% Pt/OMS-2 (cryptomelane-type manganese oxide) was prepared as reported previously. 41 1-Butanethiol (99%) and thiophenol ($99%) were purchased from Sigma-Aldrich.
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