Structural and Optical Insights Into a Phenothiazine-derived Chalcone Synthesized via Eco-friendly Methods

Authors

  • Ștefana GRAMA Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Corresponding author: bianca.stoean@ubbcluj.ro.
  • Bianca STOEAN Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: bianca.stoean@ubbcluj.ro. https://orcid.org/0000-0001-6313-6018
  • Alexandru TURZA Department of Mass Spectrometry, Chromatography and Applied Physics, National Institute for Research and Development of Isotopic and Molecular Technologies, Cluj-Napoca, Romania. Email: aturza@itim-cj.ro. https://orcid.org/0000-0002-1920-9272
  • Dan Ioan PORUMB Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: ioan.porumb@ubbcluj.ro. https://orcid.org/0000-0001-6388-2686
  • Castelia CRISTEA Faculty of Chemistry and Chemical Engineering, Babeș-Bolyai University, Cluj-Napoca, Romania. Email: castelia.cristea@ubbcluj.ro. https://orcid.org/0000-0003-1138-2596
  • Luminița SILAGHI-DUMITRESCU Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, Cluj-Napoca, Romania. Email: lusi@chem.ubbcluj.ro. https://orcid.org/0000-0001-8800-4839

DOI:

https://doi.org/10.24193/subbchem.2023.4.01

Keywords:

Phenothiazine; Chalcone; Sonochemistry; Mechanochemistry, UV-vis spectroscopy, XRD

Abstract

A novel chalcone containing (hetero)aromatic units was obtained by the Claisen-Schmidt condensation of phenothiazinyl-3-carbaldehyde with 4-hydroxy-acetophenone under three experimental approaches based on classical, mechanochemical and ultrasound-assisted procedures. A comparison between the experimental outcomes emphasizes shorter reaction time and lower energy usage in the case of mechanochemical and ultrasound-assisted procedures, recommending these methods as more environmentally friendly synthetic options. Moreover, the use of the sonochemical method resulted in the formation of the reaction product in crystalline state thus simplifying the purification process. The optical properties of the new chalcone were assessed by UV-vis spectroscopy. (E)-1-(4-hydroxyphenyl)-3-(10-methyl-10H-phenothiazin-3-yl)prop-2-en-1-one exhibited an intense absorption in the UV region (λₘₐₓ=408 nm) and low intensity fluorescence emission in DMSO solution (λₑₘ=560 nm, Stokes shift 7558 cm-1). The X-ray diffraction on monocrystal technique which was employed to ascertain the solid-state structure of the new chalcone revealed strong O-H···O hydrogen bonds and weak dispersive van der Waals interactions such as π···π and C-H···π contacts ensuring its supramolecular architecture, crystal cohesion and stability.

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Published

2023-12-20

How to Cite

GRAMA, Ștefana ., STOEAN, B. ., TURZA, A. ., PORUMB, D. I. ., CRISTEA, C. ., & SILAGHI-DUMITRESCU, L. . (2023). Structural and Optical Insights Into a Phenothiazine-derived Chalcone Synthesized via Eco-friendly Methods. Studia Universitatis Babeș-Bolyai Chemia, 68(4), 7–16. https://doi.org/10.24193/subbchem.2023.4.01

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