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

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

Journal Name: Current Organic Synthesis

Volume 17 , Issue 6 , 2020

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Graphical 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 metal-phthalocyanines can be excited by ultraviolet light and emit a fluorescence in far-red region.

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

Materials and Methods: The reaction of 4- nitro Phthalonitrile and 4- amino Phthalonitrile with ZnCl2 in the presence of dimethyl amino ethanol afforded 4,4',4' '-triamino-4' ' '-nitro zinc phthalocyanine. This product 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 4,4',4' '-tri-(dodecenyl succinic anhydride)-4' ' '-(5-amino salicylic acid) zinc phthalocyanine(I), the target compound.

Results and Discussion: 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 4,4',4' '-tri-(dodecenyl succinic anhydride)-4' ' '-(5-amino salicylic acid) zinc phthalocyanine (I), tetra-(5-amino salicylic acid) zinc phthalocyanine(E) and 4,4',4' '- triamino-4' ' '-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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Article Details

Year: 2020
Page: [488 - 495]
Pages: 8
DOI: 10.2174/1570179417666200519091950
Price: $65

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