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

Hussein Ali Al-Bahrani; Mohanad Mousa Kareem; Abdul Amir Kadhum; Nour A Alrazzak

doi:10.2174/1570179417666200519091950

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

Curr Org Synth. 2020;17(6):488-495. doi: 10.2174/1570179417666200519091950.

Authors

Hussein Ali Al-Bahrani¹, Mohanad Mousa Kareem², Abdul Amir Kadhum³, Nour A Alrazzak⁴

Affiliations

¹ College of Nursing, University of Al-Ameed, Karbala, Iraq.
² Departmemt of Chemistry, College of Science, University of Babylon, Hilla, Iraq.
³ Faculty of Medicine, University of Al-Ameed, Karbala, Iraq.
⁴ Departmemt of Chemistry, College of Science for Women, University of Babylon, Hilla, Iraq.

PMID: 32427085
DOI: 10.2174/1570179417666200519091950

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: 4-amino phthalonitrile; 4-nitro phthalonitrile; 5-amino salicylic acid; Zinc phthalocyanine; dimethylaminoethanol; dodecenyl succinic anhydride..