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14 protocols using 4 bromobenzaldehyde

1

Purification and Characterization of Aldehydes

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All solvents used for FCC and reactions were purchased from POCH (Poland). Dichloromethane (DCM), ethyl acetate (AcOEt), hexane, toluene, diethyl ether (Et2O), and acetone were purified by fractional distillation.. All inorganic compounds were purchased from ChemPure (Poland) and used without prior purification. 2-Chloro-N,N-dimethylethylamine hydrochloride (99%), 1,3-acetonedicarboxylic acid (tech. grade), glutaraldehyde (50% wt.% in H2O), methylamine hydrochloride (≥98%), 4-fluorobenzaldehyde (98%), 4-chlorobenzaldehyde (97%), 4-bromobenzaldehyde (99%), 4-nitrobenzaldehyde (98%), 4-(trifluorometyl)benzaldehyde (97%), 4-methoxybenzaldehyde (≥98%), 3-methoxybenzaldehyde (≥97%), 3,4-dimethoxybenzaldehyde (99%), 3,4,5-trimethoxybenzaldehyde (98%), and vanillin (≥97%) were obtained from Merck and used without prepurification.
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2

Synthesis of Pyridylphenylene Polymer

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Nickel (II) acetylacetonate (Acros Organics, 97%), benzyl ether (Sigma-Aldrich, 98%), potassium phosphate (Merck, 99%), phenylboronic acid (Merck, 95%), and 4-bromobenzaldehyde (Merck, 99%) were used as received. N,N-dimethylformamide (Acros Organics, 99.8%, extra dry) was used without further purification. Acetone (99.5%) and ethanol (99.8%) were purchased from Sigma-Aldrich and used without purification. Hyperbranched pyridylphenylene polymer (PPP) was synthesized as described in [39 (link)]. According to size-exclusion chromatography (SEC), the average molecular weight of the polymer was 23,403 g/mol.
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3

Synthesis and Characterization of Thiophene-Pyrrole Dyes

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2,4-Dimethylpyrrole
(≥ 97.0, Sigma-Aldrich), 4-bromobenzaldehyde (≥ 99.0,
Sigma-Aldrich), trifluoroacetic acid (≥ 99.0, Sigma-Aldrich),
DDQ (≥ 98.0, Sigma-Aldrich), boron trifluoride diethyl etherate
(≥ 98.0, TCI), 5-formyl-2-thienylboronic acid (≥ 95.0,
Sigma-Aldrich), bis(triphenylphosphine)palladium(II) dichloride (≥
98.0, Sigma-Aldrich), n-hexane (HPLC grade, ≥ 99.0, Sigma-Aldrich),
dichloromethane (anhydrous, ≥ 99.9, Sigma-Aldrich), acetonitrile
(anhydrous, ≥ 99.9, Sigma-Aldrich), ethanol (≥ 99.8,
Sigma-Aldrich), chloroform (≥ 99.8, Sigma-Aldrich), and ethyl
acetate (anhydrous, ≥ 99.8, Sigma-Aldrich) were used. All metal
salts were used as their water-soluble sulfate, nitrate, or chloride
salts, purchased from Sigma-Aldrich (≥ 95). A Varian VNMRJ
600 nuclear magnetic resonance spectrometer was used for 1H NMR and 13C NMR measurements. Mass analysis was conducted
with a Thermo Q-Exactive Orbitrap device. Ultraviolet–visible
(UV–vis) absorption spectra were obtained with a spectrophotometer
(Shimadzu 1900i). Fluorescence emission measurements were obtained
using a Varian Cary Eclipse fluorescence spectrophotometer. Quantum
yield measurements were conducted with a Hamamatsu Quantaurus-QY absolute
PL quantum yield spectrometer.
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4

Synthesis and Characterization of BODIPY Dyes

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4-Acetamidobenzaldehyde, 4-bromobenzaldehyde, N-bromosuccinimide (NBS), boron trifluoride diethyl etherate (BF3·OEt2), 2,4-dimethylpyrrole, glacial acetic acid, piperidine, Rhodamine 6G, anhydrous sodium sulfate (Na2SO4), tetrachloro-1,4-benzoquinone (p-chloranil), triethylamine (TEA), trifluoroacetic acid (TFA), and zinc phthalocyanine were purchased from Sigma-Aldrich. Spectroscopic grade solvents were used for the photophysical and the open aperture Z-scan studies.
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5

Synthesis of Substituted Benzaldehydes

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3-anisaldehyde (97%), 4-anisaldehyde (99+%), 3-tolualdehyde (98%), 3-nitroBenzaldehyde (99%), and 3-bromoBenzaldehyde (96%) were acquired from Acros organics (NJ, USA). 2-hydroxyBenzaldehyde, ethyl acetoacetate (99%), 4-hydroxyBenzaldehyde, 4-nitroBenzaldehyde (98%), 4-cloroBenzaldehyde (97%), 4-bromoBenzaldehyde (99%), ethyl vanillin (98%), piperonal (99%), and piperidine (≥99.5%) were purchased from Sigma-Aldrich Co. (St. Louis, MO, USA). Benzaldehyde was obtained from Merck (Hohenbrunn, Germany) and Aldrich Co. (Milwaukee, WI, USA).
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6

Preparation of Bis-Schiff Base Corrosion Inhibitors

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Analytical grade chemicals and solvents were used for the synthesis of the bis-Schiff bases. All the solvents, including benzaldehyde, 4-bromobenzaldehyde, and 4-hydroxybenzaldehyde, were purchased from Sigma Aldrich and used without further purification. GR grade HCl (35%) was obtained from Merck. Mild steel specimens with an elemental composition of C: 0.17%, Si: 0.59%, Mn: 1.6%, P: 0.040% and iron for the rest were used. Specimens of dimensions 2 × 2 × 0.1 cm were used for all experiments. Before the commencement of electrochemical and gravimetric experiments, the mild steel specimens were polished with emery paper of 600, 800 and 1200 grades under running tap water. These were washed with distilled water, dried with a clean tissue, and finally immersed in benzene and acetone for a few seconds before air drying.22,23 (link)
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7

Synthesis and Antimicrobial Evaluation

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All analytical grade chemicals and solvents were used as commercially received. HAuCl4.3H2O was purchased from S.D. Fine-Chem Ltd. (India.). 2,2-Dipyridylketone, 2-benzoyl pyridine, benzaldehyde, 4-methyl benzaldehyde, 4-bromo benzaldehyde, 4-chloro benzaldehyde, 4-methoxy benzaldehyde, HS-DNA and EDTA were purchased from Sigma Aldrich Chemical Co. (India). Agarose, Luria Broth (LB), ethidium bromide (EtBr), Tris–acetyl–EDTA (TAE) and bromophenol blue were purchased from Himedia (India). Culture for antibacterial activity Bacillus subtilis (B. subtilis-7193), Staphylococcus aureus (S. aureus-3160), Pseudomonas aeruginosa (P. aeruginosa-1688), Escherichia coli (E. coli-433) and Serratia marcescens (S. marcescens-7103) were purchased from the Institute of Microbial Technology (Chandigarh, India). S. Pombe Var. Paul Linder 3360 was obtained from IMTECH, Chandigarh.
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8

Synthesis of Ni-tetra(4-phosphonophenyl)porphyrin

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ZrOCl2·8H2O (99.5%, Sigma Aldrich), HfCl4 (98%, Sigma Aldrich), NiCl2·6H2O (97%, Merck), EtOH (99% + 1% MEK, Walther), dichloromethane (Walther), N,N-dimethylformamide (99%, Grüssing), acetone (99%, Walther), 100% acetic acid (VWR chemicals), NaH2PO4 (99%, Sigma-Aldrich) and Na2HPO4 (99%, Sigma-Aldrich) were used without further purification. The linker Ni-4,4′,4′′,4′′′-(5,10,15,20-porphyrintetrayl)-tetraphosphonobenzoic acid (Ni-tetra(4-phosphonophenyl)porphyrin, Ni-H8TPPP) was synthesized according to reported procedures67 –69 starting with 4-bromobenzaldehyde (99%, Sigma Aldrich) and pyrrole (98%, ABCR) in propionic acid (99%, Grüssing) with following NiCl2-catalyzed (97%, Merck) phosphonylation in 1,3-diisopropylbenzene (96%, Sigma-Aldrich) using triethyl phosphite (98%, Sigma-Aldrich) with following hydrolysis in conc. HCl (35%, VWR chemicals). Details are given in the ESI.
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9

Benzaldehyde Derivatives Synthesis Protocols

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Benzaldehyde (99%), 4-methoxyBenzaldehyde (98%), 4-chloroBenzaldehyde (98%), 4-fluoroBenzaldehyde (98%), 2-fluoroBenzaldehyde (97%), 4-bromoBenzaldehyde (99%), 4-methylBenzaldehyde (97%), 2-furaldehyde (99%), ammonium acetate (97%), 2-chloroBenzaldehyde (99%) were purchased from Sigma-Aldrich. 1,3-Cyclohexadione (97%), acetophenone (98%), malononitrile (99%), and dimedone (99%) were acquired from Acros.
Ethyl acetate (for analysis EMSURE ACS, ISO, Reag. Ph Eur) and acetone (for analysis EMPARTA ACS) were acquired from Merck. Thin-layer chromatography (TLC) was conducted using aluminum plates (F-254) covered with silica gel. The experiment included the use of silica gel (230–400 mesh, Merck) for column chromatography.
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10

Synthesis of Organic Compounds

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All the chemicals were obtained from commercial suppliers and were used without further purification. Lead iodide (99.99%, PbI2) and iodine (≥99.99%, I2) were purchased from Alfa Aesar. N,N-Dimethyl formamide (DMF) and hydroiodic acid (55% w/w, HI) were purchased from Fisher Scientific. Benzaldehyde, 2-methoxyBenzaldehyde, 4-chloroBenzaldehyde, 4-bromoBenzaldehyde, 3-nitroBenzaldehyde, cinnamaldehyde, 2-methoxycinnamaldehyde, salicylaldehyde, 2-nitrocinnamaldehyde, benzophenone, and methylamine solution (33 wt% in ethanol) were purchased from Sigma-Aldrich.
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