Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8F4N2
With reference to Compounds 15 and 16, an exemplary synthesis and characterization of F34 cZn (hereinafter “Compound 15″) and F52Pc’Zn (hereinafter”Compound 16”) are depicted. In particular, twenty (20) thick walled glass reaction vessels(about 10 mL volume) are charged each with about 0.4 g (about 0.62 mmol) perfluoro-3,5,6- triisopropyl phthalonitrile, (depicted in FIG. 1 1 as P3 and hereinafter “Compound 14″), about0.04 g (about 0.2 mmol) tetrafluorophthalonitrile (depicted in FIG. 1 1 as P0 and hereinafter”Compound 13”) and about 0.04 g (about 0.22 mmol) zinc(II) acetate dihydrate. Then, catalytic amounts of ammonium molibdate, and about 1 mL nitrobenzene are added to each vial. The sealed vessels are heated in a microwave reactor at approximately 180 ¡ãC for about1 min. The crude solid of each vial is extracted with about 50 mL ethyl acetate, the organic fractions are combined, concentrated in vacuo and adsorbed to silica gel (mesh size approximately 70-230). Gel filtration using an acetone/hexane approximately 2:98 mixture(v/v) allows for the complete separation of nitrobenzene, unreacted Compound 14 and most yellowish impurities. The resulting blue-green solid is collected and subjected to column chromatography under gradually increasing solvent polarity. The rest of yellow impurities are removed with acetone/hexane approximately 2:98 mixture, followed by the separation of the green exemplary F52Pc’Zn, eluted with an approximately 10:90 mixture, the royal blue exemplary F34PcZn at approximately 20:80 polarity, and finally the dark blue exemplary Fi6PcZn as a side product using an approximately 40:60 mixture (v/v). The three colored fractions are evaporated and re-purified by gel filtration on short columns, eluting with the corresponding mixtures used for their initial separation. Removal of the solvent and drying of the compounds allows for isolation of exemplary FsaPc’Zn in about 13percent yield (about 0.42 g), exemplary T^PcZn in about 16percent yield (about 0.26 g) and exemplary FigPcZn in about 14percent yield (about 0.1 g), all based on starting material Compound 13.[0098] Specifically, the exemplary properties for Compound 15, i.e., F34PcZn, are as follows: Mp > 300 ¡ãC; UV-vis (CHC13): max (log e) 689 (5.09), 672 (4.99), 632 (4.44), 614 (4.41), 365 (4.69) nm (L mol 1 cm 1); IR (KBr): 1522, 1489, 1383, 1282, 1236, 1 133, 964 cm”1; 19F NMR (282 MHz, (CD3)2CO): delta -69.05 (6F, br, CF3), -72.25 (12F, s, CF3), -97.12 (IF, s, Ar-F), -131.4 (IF, s, CF), -135.09 (I F, d, Ar-F), -139.18 to -141.66.(5F, m, Ar-F), -149.92 to -151.6 (6F, m, Ar-F), -161.39 (IF, d, CF), -165.99 to -170.18 (I F, m, CF); HRMS (APCI+): calcd. for [M + H]+ (C4iHF34N8Zn)+ 1314.9067, found 1314.9080.[0099] With reference to FIG. 12, the measured exact mass spectrum (positive ion APCI) and isotope pattern of [M + H]+ for F34PcZn are depicted, indicating the calculated value for [M + H]+.[00100] Turning now to FIGS. 13(a)-(b), the UV-Vis electronic absorption spectra of F34PcZn are illustrated, showing solvent- dependent aggregation. In particular, FIG. 33(a) illustrates a spectrum recorded in chloroform, in which F34PcZn is a monomer, and FIG. 13(b) illustrates a spectrum recorded in ethanol, in which F34PcZn displays a significant degree of dimerization.[00101] Further, the exemplary properties for Compound 16, i.e., F52Pc’Zn, are as follows: Mp > 300 ¡ãC; UV-vis (CHC13): Xmm (log epsilon) 701 (5.10), 674 (4.97), 640 (4.62), 615 (4.44), 372 (4.78) nm (L mol”1 cm”1); IR (KBr): 1523, 1489, 1375, 1287, 1236, 1 166, 1 127, 1050, 966, 939, 737 cnT1 ; 19F NMR (282 MHz, (CD3)2CO): delta -63.23 (3F, br, C3/4 -68.52 (3F, br, CF3), -70.69 to -76.31 (30F, m, CF ), -97.56 (2F, br, Ar-F), -130.85 (I F, d, CF), -137.91 to -141 .55 (5F, m, Ar-F), -151.23 to -152.76 (4F, m, Ar-F), -161 .49 (I F, d, CF), -166.47 to -170.15 (3F, m, CF); HRMS (APCI+): calcd. for [M + H]+ 1764.8780, found 1764.8804.[00102] With reference to FIG. 14, the measured exact mass spectrum (positive ion APCI) and isotope pattern of [M + H].bul. for F52 c’Zn are depicted, indicating the calculated value for [00103] Turning now to FIG. 15, the X-ray structure of F52Pc’Zn(OPPh3) is depicted, showing a metal-coordinated triphenyl phosphine oxide molecule. The thermal ellipsoids are plotted at about 35percent probability and rotational disorder of the CF3 groups of -C3F7 is present, specifically shown as dashed lines.[00104] With reference to FIG. 16, the side view of the aggregation in solid state of F52Pc’Zn is illustrated. In particular, the toluene molecules in the crystalline lattice and the atoms of coordinated triphenyl phosphine oxide, except oxygen, have been omitted. Further, the /-C3F7 groups are shown in ball-and-stick representation and the interplanar stacking distance, approximately 3.663 A, proves the existence of pi-pi interactions.
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1835-65-0.
Reference:
Patent; NEW JERSEY INSTITUTE OF TECHNOLOGY; GORUN, Sergiu, M.; LOAS, Andrei, Ioan; GRISWOLD, Kimberly; LAPOK, Lukasz; PATEL, Hemantbhai, Hasmukhbhai; GERDES, Robert; WO2012/61344; (2012); A1;,
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