In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1835-65-0 as follows. name: 3,4,5,6-Tetrafluorophthalonitrile
With reference to Compounds 17 and 18, an exemplary synthesis and characterization of F34PcCo (hereinafter “Compound 17”) and F52Pc’Co (hereinafter “Compound 18”) is depicted. In particular, Compounds 17 and 18 are prepared similarly to Compounds 15 and 16, using sixteen (16) glass vessels, each charged with about 0.3 g (about 0.47 mmol) of Compound 14, about 0.05 g (about 0.25 mmol) of Compound 13 and about 0.045 g (about 0.18 mmol) cobalt(II) acetate tetrahydrate. Microwave heating is performed for approximately 12 min at about 185 ¡ãC. Initial purification of the brute solid by gel filtration is done with a toluene hexane approximately 1 :9 mixture (v/v). The rest of the separations are carried out as described for Compounds 1 and 16. Evaporation of the eluted fractions and drying to constant weight allows for isolation of green exemplary F52Pc’Co (Compound 18) in about 1.5percent yield (about 0.05 g), exemplary F34PcCo (Compound 17) in about 1 1 percent yield (about 0.19 g) and exemplary F]6PcCo as a side product in about 10percent yield (about 0.084 g), based on starting material Compound 13. About 4.5 g of Compound 14 are recovered following the initial separation (about 90percent of initial amount). X-ray quality single crystals for exemplary F34PcCo are obtained by slow evaporation of an acetonitrile/toluene approximately 1 :1 solution.[00106] Specifically, the exemplary properties of Compound 17, i.e., F34PcCo, are as follows: Mp > 300 ¡ãC; UV-vis (CHCI3): lmm (log e) 680 (4.52), 667 (4.50), 61 1 (4.03) nm (L moF1 cm-1); 19F NMR (282 MHz, (CD3)2CO): delta -63.58 (3F, br, GF3), -67.36 (3F, s, CF3), -68.75 to -76.79 (12F, m, CF3), -100.98 (I F, br, Ar-F), -132.36 (I F, s, CF), -137.64 (I F, d, Ar-F), -139.44 to -142.63 (5F, m, Ar-F), -155.92 to -157.62 (6F, m, Ar-F), -165.55 (I F, d, CF), -169.46 (IF, br, CF); HRMS (APCI-): calcd. for [M]~ (C41F34N8C0) 1308.9040, found 1308.9032.[00107] With reference to FIG. 17, the measured exact mass spectrum (negative ion APCI) and isotope pattern of [M]~ for F34PCC0 are depicted, indicating the calculated value for [M]~.[00108] Turning now to FIG. 18(a), the side view of the aggregation in solid state of F34PCC0 is illustrated. In particular, the toluene molecules in the crystalline lattice and the H atoms of coordinated acetonitrile have been omitted and the Z-C3F7 groups are depicted as van der Waals spheres. The interplanar stacking distance, approximately 3.25 A, illustrates the existence of pi-pi interactions. With reference to FIG. 18(b), a top view of the pi-pi stacking region of two adjacent molecules of F34PCC0 is depicted.[00109] With reference to FIG. 19, the X-ray structure of F34PcCo(CH3CN) is depicted, showing a metal-coordinated acetonitrile molecule. In particular, the thermal ellipsoids are plotted at about 40percent probability and rotational disorder of the CF3 groups of -C3F7 is present, as is shown by the dashed lines.[00110] Further, the exemplary properties of Compound 18, i.e., Fs2Pc’Co, are as follows: Mp > 300 ¡ãC; UV-vis (CHC13): max (log e) 686 (4.62), 615 (4.1 8), 334 (4.58) nm (L mol”1 cm”1); l9F NMR (282 MHz, (CD3)2CO): delta -63.62 (3F, br, C73/4, -67.01 to -76.28 (33F, m, CF3), -90.0 to -1 10.0 (2F, br, Ar-F), -137.5 to -147.5 (6F, m, Ar-F), -155.0 to – 1 59.5 (4F, br, Ar-F), -165.82 (I F, m, CF), -169.76 to -171.73 (3F, m, CF); HRMS (APC1-): calcd. for [M]~ (C5oF52NgCor 1758.8753, found 1758.8763.[00111] With reference to FIG. 20, the measured exact mass spectrum (negative ion APCI) and isotope pattern of [M]~ for F52Pc’Co are depicted, indicating the calculated value for [Mf.[00112] Turning now to FIG. 21 (a), a ball-and-stick representation ofF34PcZn(H20)*((CH3)2CO)2 is depicted showing H-bonding between the H atoms of H20 and the oxygen atoms (02) of the two acetone molecules. FIG. 21(b) is a van der Waals representation of the exemplary F3 PcZn(H20)*((CH3)2CO 2. FIG. 21(c) illustrates the side view of the aggregation in solid state of exemplary p34PcZn. The acetone molecules in the crystalline lattice and the H atoms of coordinated H2O have been omitted for clarity. The i-C3F7 groups are depicted as van der Waals spheres. The interplanar stacking distance, about3.393 A, demonstrates the existence of pi-pi interactions. Further, FIG. 21 (d) illustrates a top view of the pi-pi stacking region of two adjacent molecules of exemplary F34PCZ11. [0PsiPi3] Turning now to FIG. 22, the X-ray structure of F3 Pc2n(H20) is illustrated, showing a metal -coordinated water molecule. In particular, the acetone molecules in the crystalline lattice have been omitted. The thermal ellipsoids of FIG. 22 are plotted at about 40percent probability.
According to the analysis of related databases, 1835-65-0, the application of this compound in the production field has become more and more popular.
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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