Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors

Patrascu, Bianca; Mocanu, Sorin; Coman, Anca; Madalan, Augustin M.; Popescu, Codruta; Paun, Anca; Matache, Mihaela; Ionita, Petre

doi:10.3390/ijms21103559

Open AccessArticle

Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors

by

Bianca Patrascu

¹,

Sorin Mocanu

²,

Anca Coman

¹,

Augustin M. Madalan

³,

Codruta Popescu

¹,

Anca Paun

¹,

Mihaela Matache

¹ and

Petre Ionita

^1,*

¹

Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, Panduri 90-92, 050663 Bucharest, Romania

²

Institute of Physical Chemistry, Spl. Independentei 202, 060021 Bucharest, Romania

³

Department of Inorganic Chemistry, Faculty of Chemistry, University of Bucharest, Dumbrava Rosie 23, 020462 Bucharest, Romania

^*

Author to whom correspondence should be addressed.

Int. J. Mol. Sci. 2020, 21(10), 3559; https://doi.org/10.3390/ijms21103559

Submission received: 30 April 2020 / Revised: 14 May 2020 / Accepted: 16 May 2020 / Published: 18 May 2020

(This article belongs to the Special Issue Synthesis and Reactivity of Novel Aromatic Compounds)

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Abstract

Starting from dansyl-chloride, in reaction with 1,1-diphenylhydrazine and methoxyamine, two new fluorescent derivatives 1 and 2 were obtained and characterized by NMR, IR, UV-Vis, HR-MS, and fluorescence spectroscopy. The single-crystal X-ray structure was obtained for compound 2. Both compounds generate free radicals by oxidation, as demonstrated by ESR spectroscopy. Compound 1 generates the corresponding hydrazyl-persistent free radical, evidenced directly by ESR spectroscopy, while compound 2 generates in the first instance the methoxyaminyl short-lived free radical, which decomposes rapidly with the formation of the methoxy radical, evidenced by the ESR spin-trapping technique. By oxidation of compounds 1 and 2, their fluorescence is quenched.

Keywords: dansyl; fluorescence; free radical; hydrazyl

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MDPI and ACS Style

Patrascu, B.; Mocanu, S.; Coman, A.; Madalan, A.M.; Popescu, C.; Paun, A.; Matache, M.; Ionita, P. Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors. Int. J. Mol. Sci. 2020, 21, 3559. https://doi.org/10.3390/ijms21103559

AMA Style

Patrascu B, Mocanu S, Coman A, Madalan AM, Popescu C, Paun A, Matache M, Ionita P. Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors. International Journal of Molecular Sciences. 2020; 21(10):3559. https://doi.org/10.3390/ijms21103559

Chicago/Turabian Style

Patrascu, Bianca, Sorin Mocanu, Anca Coman, Augustin M. Madalan, Codruta Popescu, Anca Paun, Mihaela Matache, and Petre Ionita. 2020. "Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors" International Journal of Molecular Sciences 21, no. 10: 3559. https://doi.org/10.3390/ijms21103559

APA Style

Patrascu, B., Mocanu, S., Coman, A., Madalan, A. M., Popescu, C., Paun, A., Matache, M., & Ionita, P. (2020). Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors. International Journal of Molecular Sciences, 21(10), 3559. https://doi.org/10.3390/ijms21103559

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Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors

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