New olefinic centred binuclear clamshell type phthalocyanines: Design, synthesis, structural characterisation, the stability and the change in the electron cloud at olefine-based symmetrical diphthalonitrile fragment by the combined application of UV-Vis electronic structure and theoretical methods

Degirmencioglu, IsmailBayrak, RizaEr, MustafaSerbest, Kerim2024-09-292024-09-2920110277-53871873-3719https://doi.org/10.1016/j.poly.2011.03.039https://hdl.handle.net/20.500.14619/5219The olefinic centred Schiff base (3) was obtained from the condensation of substituted dialdehyde (1) with 2-amino-4-methylphenol (2) in a 1:2 ratio. The diphthalonitrile derivative (5) was prepared by the reaction of 4-nitrophthalonitrile (4) and compound (3) in dry dimethylformamide/potassium carbonate. The key product (5) was obtained by nucleophilic substitution of an activated nitro group into an aromatic ring. The cyclotetramerization of compound (5) with phthalonitrile (6) in 1:6.15 ratio gave the expected metal-free phthalocyanine of clamshell type (7), and with metal salts of Zn(II), Ni(II), Co(II) and Cu(II) gave metallophthalocyanines of clamshell types (8-11), respectively in dimethylaminoethano1/1,8-diazabycyclo[5.4.0]undec-7-ene system. The products were purified by several techniques such as crystallization and preparative thin layer chromatography. The newly prepared compounds were characterised by a combination of elemental analyses, IR, H-1/C-13 NMR, MS and UV-Vis spectroscopy. (C) 2011 Elsevier Ltd. All rights reserved.eninfo:eu-repo/semantics/closedAccessPhthalocyanineMetallophthalocyanineBinuclearClamshellSchiffs baseOlefinic centredNew olefinic centred binuclear clamshell type phthalocyanines: Design, synthesis, structural characterisation, the stability and the change in the electron cloud at olefine-based symmetrical diphthalonitrile fragment by the combined application of UV-Vis electronic structure and theoretical methodsArticle10.1016/j.poly.2011.03.0392-s2.0-7995575235316369Q2162830WOS:000291498600025Q2