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Alireza Karimi

Alireza Karimi

Academic rank: Professor
ORCID: https://orcid.org/0000-0001-5006-8642
Education: PhD.
ScopusId: 57217189368
Faculty: Science
Address: Arak University
Phone:

Research

Title
Synthesis of newhighlyorganosolublemetallophthalocyanineswith 1,8-dioxo-octahydroxanthenesubstituents
Type
JournalPaper
Keywords
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Year
2011
Journal Tetrahedron Letters
DOI
Researchers Alireza Karimi ، Fahimeh Bayat

Abstract

Newhighlyorganosolublemetallophthalocyanines (M = Zn, Co, Ni and Cu) bearing four [4-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenoxy] substituents at peripheral positions have been prepared by tetramerization of 4-[4-(3,3,6,6-tetramethyl-1,8-dioxo-dodecahydro-1H-xanthen-9-yl)phenoxy]phthalonitrile in 2-(dimethylamino)ethanol using microwave irradiation or conventional heating. Ni(II), Co(II), and Cu(I) chloride were employed in order to synthesize the corresponding metal phthalocyanines and Zn(OAc)2 was used for the preparation of the zinc phthalocyanines. 4-[4-(3,3,6,6-Tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenoxy]phthalonitrile was obtained by nucleophilic displacement of the nitro group in 4-nitrophthalonitrile with 9-(4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-dione. 9-(4-Hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-dione was synthesized efficiently from dimedone and 4-hydroxybenzaldehyde. All the phthalocyanines are soluble in DMSO, DMF, CHCl3, THF, CH2Cl2, and CH3CN. The new compounds were characterized by IR, NMR, and UV–vis spectroscopy, elemental analysis, and thermogravimetric analysis.