Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
UDK 547.552 Гомологи анилина
The paper investigates the influence of the nature of N-nucleophiles on the reaction of activated aromatic nucleophilic substitution of chlorine atom in 4,5-dichlorophthalonitrile. The authors synthesised 4-chloro-5-(R-amino)phthalonitriles not described in the literature. They are promising compounds for the synthesis of phthalocyanines with increased organosolubility.
4,5-dichlorophthalonitrile, N-nucleophiles, amines, SNAr reaction, phthalocyanines, 4-chloro-5-(R-amino)phthalonitriles
1. Wöhrle, D., Eskes, M., Shigehara, K. & Yamada, A. (1993) A simple synthesis of 4,5-disubstituted 1,2-dicyanobenzenes and 2,3,9,10,16,17,23,24-octasubstituted phthalocyanines, Synthesis, 2, pp. 194-196. DOI:https://doi.org/10.1055/S-1993-25825.
2. Matlaba, P.M. (2002) Synthesis of zinc phthalocyanine derivatives for possible use in photodynamic therapy. MA thesis. Grahamstown.
3. Sabeeha, S.M. (2014) Phthalocyanine-based molecules and polymers of intrinsic microporosity. PhD. Cardiff.
4. Alharbi, N. (2014) Synthesis and functionalization of novel meso-substituted tetrabenzotriazaporphyrins. PhD, Norwich.
5. Matemadombo, F., Maree, M.D., Ozoemena, K.I., Westbroek, P. & Nyokong, T. (2005) Synthesis, electrochemical and spectroelectrochemical studies of octaphenylthio-substituted phthalocyanines, Journal of Porphyrins and Phthalocyanines, 9(7), pp. 484-491. DOI:https://doi.org/10.1142/S1088424605000605.
6. Abramov, I.G., Baklagin, V.L., Bukhalin, V.V., Maizlish, V.E. & Rassolova, A.E. (2022) Synthesis of substituted aryloxyphthalonitriles based on 4-chlorophthalonitrile and 4,5-dichlorophthalonitrile, From Chemistry Towards Technology Step-By-Step, 3(4), pp. 102-109 [online]. Available at: https://ystu.editorum.ru/en/nauka/issue/5030/view (accessed 10.03.2024). DOI:https://doi.org/10.52957/27821900_2022_04_102. (in Russian).
7. Venkatramaiah, N., Rocha, D.M.G.C., Srikanth, P., Paz, F.A.A. & Tomé, J.P. C. (2015) Synthesis and photophysical characterization of dimethylamine-derived Zn(ii)phthalocyanines: exploring their potential as selective chemosensors for trinitrophenol, Journal of Materials Chemistry C, 3, pp. 1056-1067. DOI:https://doi.org/10.1039/C4TC02253J.
8. Gümüş, G. & Ahsen, V. (2002) Synthesis and characterization of di-n-hexylamino-substituted phthalocyanines, Journal of Porphyrins and Phthalocyanines, 6(7), pp. 489-493. DOI:https://doi.org/10.1142/S1088424602000610.
9. Burat, A.K., Koca, A., Lewtak, J.P. & Gryko, D.T. (2010) Synthesis, physicochemical properties and electrochemistry of morpholine-substituted phthalocyanines, Journal of Porphyrins and Phthalocyanines, 14(7), pp. 605-614. DOI:https://doi.org/10.1142/S108842461000246X.
10. Roberts, J.M. (2016) Synthesis, spectroscopic studies, and computational analysis of a solvatochromic phthalocyanine derivative. MA thesis. Tucson.
11. Burat, A.K., Koca, A., Lewtak, J.P. & Gryko, D.T. (2011) Preparation, electrochemistry and optical properties of unsymmetrical phthalocyanines bearing morpholine and tert-butylphenoxy substituents, Synthetic Metals, 161(15-16), pp. 1537-1545. DOI:https://doi.org/10.1016/j.synthmet.2011.05.010.
12. Green, J., Hopkins, M., Jones, B., Kiryanov, A.A., Kuehler, J., Monenschein, H., Murphy, S., Nixey, T. & Sun, H. (2020) Piperidinyl- and piperazinyl-substituted heteroaromatic carboxamides as modulators of GPR6. 20200375969 US.
13. Tshivhase, M. & Williams, D.B.G. (2014) Color-Coded Ligands: Tracking the Catalyst using Highly Pigmented Porphyrazine Ligands in Biphasic Reactions, Organometallics, 33(24), pp. 7023-7026. DOI:https://doi.org/10.1021/om501094p.
14. Dehe, D., Lothschütz, C. & Thiel, W.R. (2010) Novel pyrazole functionalized phthalocyanines and their first row transition metal complexes, New Journal of Chemistry, 34, pp. 526-532. DOI:https://doi.org/10.1039/B9NJ00485H.
15. Majeed, S.A., Ghazal, B., Nevonen, D.E., Goff, P.C., Blank, D.A., Nemykin, V.N. & Makhseed, S. (2017) Evaluation of the Intramolecular Charge-Transfer Properties in Solvatochromic and Electrochromic Zinc Octa(carbazolyl)phthalocyanines, Inorganic Chemistry, 56(19), pp. 11640-11653. DOI:https://doi.org/10.1021/acs.inorgchem.7b01570.
16. Majeed, S.A., Nwaji, N., Mack, J., Nyokong, T. & Makhseed, S. (2019) Nonlinear optical responses of carbazole-substituted phthalocyanines conjugated to graphene quantum dots and in thin films, Journal of Luminescence, 213, pp. 88-97. DOI:https://doi.org/10.1016/j.jlumin.2019.04.034.