Electrochemical study of 1,5-diaminonaphthalene in aqueous solution: Assessing electrochemistry as a green synthetic tool for the synthesis of 4-imino-4H-dibenzo[a,h]phenoxazin-11-ol
Journal of the Electrochemical Society, ISSN: 1945-7111, Vol: 164, Issue: 9, Page: G87-G91
2017
- 3Citations
- 8Captures
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Article Description
The electrochemical behavior of 1,5-diaminonaphthalene (1,5DAN) was studied by cyclic voltammetry and controlled-potential coulometry methods in aqueous ethanol (water/ethanol, 70/30 v/v). The effect of different parameters such as solution pH (from 2 to 10), potential scan rate and 1,5DAN concentration on its electrochemical behavior was studied. The electrochemical synthesis of 4-imino-4H-dibenzo[a,h]phenoxazin-11-ol (IDP) was achieved in high yield (87%) by electrooxidation in water (bicarbonate buffer, c = 0.2 M, pH = 9.0)/ethanol (70/30, v/v) in a one-pot process. The proposed mechanism involves the Michael addition of 1,5DAN to 1,5-naphthalendione (from the hydrolysis of the electrogenerated naphthalene-1,5-diimine (1,5DAN)) followed by oxidation of the 1,5-diaminonaphthalene moiety, cyclization, aromatization, and a final oxidation. Polymerization of 1,5DAN was not observed. The present work provides a green and environmentally friendly method with high atom economy for the synthesis of IDP in an undivided cell under constant current. In addition, IDP showed antibacterial activity against Gram-positive bacteria Bacillus cereus and Staphylococcus aureus.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85039980407&origin=inward; http://dx.doi.org/10.1149/2.03517089jes; https://iopscience.iop.org/article/10.1149/2.03517089jes; https://syndication.highwire.org/content/doi/10.1149/2.03517089jes; https://dx.doi.org/10.1149/2.03517089jes; https://validate.perfdrive.com/9730847aceed30627ebd520e46ee70b2/?ssa=176d4438-c1c3-484e-a767-bdedb0f9064e&ssb=80341270457&ssc=https%3A%2F%2Fiopscience.iop.org%2Farticle%2F10.1149%2F2.03517089jes&ssi=ad7c3b97-cnvj-43ff-a0d5-71677f66541b&ssk=botmanager_support@radware.com&ssm=26498383536562947277183239587296808&ssn=5d0ecdc6a8ab1d7c136c0134fdea1f45f2cf1e24c69e-487b-403d-a85a2a&sso=1cb7ea49-6bec873f601531d16c58433013fdfe8a87ca0bfd67203130&ssp=88170238971730441780173077048962721&ssq=02499977901305535026170332315869231627638&ssr=NTIuMy4yMTcuMjU0&sst=com.plumanalytics&ssu=&ssv=&ssw=&ssx=eyJ1em14IjoiN2Y5MDAwNDMyZmZhZjctNjFmNy00ZTc3LWE2MDMtODU2OGRkNzFkZjNlNS0xNzMwNDcwMzMyNjYwMzA4NjgwNjI4LWUyYThjZWNjMjZkY2VkYzUyNzcxNSIsInJkIjoiaW9wLm9yZyIsIl9fdXptZiI6IjdmNjAwMDk3YzcxZDhjLWQ1MTAtNDdmYi1iMjRhLWY4NTRhMjI5NTk4YzE3MzA0NzAzMzI2NjAzMDg2ODA2MjgtNWFhNzdkZTE3YTA3ZWQ1MTI3NzE1In0=
The Electrochemical Society
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