Synthesis and Characterization of New Zinc Phthalocyanine - Dodecenyl Succinic Anhydride Benzoic Groups

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Author(s): Hussein Ali Al-Bahrani, Mohanad Mousa Kareem, Abdul Amir H. Kadhum*, Nour Abd. Alrazzak

Journal Name: Current Organic Synthesis

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Abstract:

Background: The phthalocyanines a series of compounds involves four iso-indole units linked by aza nitrogen atoms bonded with metal atoms that are normally located in the center a phthalocyanines ring. Some of the central metalphthalocyanines can be excited by ultraviolet light and emits a fluorescence in far-red region.

Objective: To synthesize a derivative of phthalocyanines namely 4,4ʹ,4ʹʹ-tri-(dodecenyl succinic anhydride)-4ʹʹʹ-(5-amino salicylic acid) zinc phthalocyanine with a zinc central metal.

Method: The reaction of 4- nitro Phthalonitrile and 4- amino Phthalonitrile with ZnCl2 in the presence of dimethyl amino ethanol afforded 4,4ʹ,4ʹʹ-triamino-4ʹʹʹ-nitro zinc phthalocyanine. This product was reacted with 5-amino salicylic acid to yield tetra-(5-amino salicylic acid) zinc phthalocyanine. A dodecenyl succinic anhydride was added on the amine group of benzoic rings to afford 4,4ʹ,4ʹʹ-tri-(dodecenyl succinic anhydride)-4ʹʹʹ-(5-amino salicylic acid) zinc phthalocyanine(I), the target compound.

Result: Compound I is successfully synthesized with a yield of 72% from tetra-(5-amino salicylic acid) zinc phthalocyanine with dodecenyl succinic anhydride.

Conclusion: The newly synthesized molecule of 4,4ʹ,4ʹʹ-tri-(dodecenyl succinic anhydride)-4ʹʹʹ-(5-amino salicylic acid) zinc phthalocyanine (I), tetra-(5-amino salicylic acid) zinc phthalocyanine(E) and 4,4ʹ,4ʹʹ-triamino-4ʹʹʹ-nitro zinc phthalocyanine (S). The reaction of 4- nitro Phthalonitrile and 4- amino and the structure of compound I is confirmed and its formation was proven.

Keywords: zinc phthalocyanine, dodecenyl succinic anhydride, 5-amino salicylic acid, 4-nitro phthalonitrile, 4-amino phthalonitrile, dimethylaminoethanol.

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(E-pub Ahead of Print)
DOI: 10.2174/1570179417666200519091950
Price: $95

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