Structural and Optical Insights Into a Phenothiazine-derived Chalcone Synthesized via Eco-friendly Methods
DOI:
https://doi.org/10.24193/subbchem.2023.4.01Keywords:
Phenothiazine; Chalcone; Sonochemistry; Mechanochemistry, UV-vis spectroscopy, XRDAbstract
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.
References
D. M. Dereje, C. Pontremoli, M. J. Moran Plata, S. Visentin and N. Barbero, Photochem. Photobiol. Sci., 2022, 21, 397–419.
H. A. Shindy, Dye. Pigment., 2017, 145, 505–513.
D. Çakir, T. Arslan and Z. Biyiklioglu, Dalt. Trans., 2015, 44, 20859–20866.
C. F. Lipinski, A. A. Oliveira, K. M. Honorio, P. R. Oliveira and A. B. F. da Silva, Struct. Chem., 2018, 29, 957–965.
C. Zhuang, W. Zhang, C. Sheng, W. Zhang, C. Xing and Z. Miao, Chem. Rev., 2017, 117, 7762–7810.
J. C. Trivedi, J. B. Bariwal, K. D. Upadhyay, Y. T. Naliapara, S. K. Joshi, C. C. Pannecouque, E. De Clercq and A. K. Shah, Tetrahedron Lett., 2007, 48, 8472–8474.
A. L. Cole, S. Hossain, A. M. Cole and O. Phanstiel, Bioorganic Med. Chem., 2016, 24, 2768–2776.
P. Mahesha, N. S. Shetty and S. D. Kulkarni, J. Fluoresc., 2022, 32, 835–862.
A. M. Craciun, M. Focsan, L. Gaina and S. Astilean, Dye. Pigment., 2017, 136, 24–30.
B. Stoean, D. Rugina, M. Focsan, A. M. Craciun, M. Nistor, T. Lovasz, A. Turza, I. D. Porumb, E. Gál, C. Cristea, L. Silaghi‐dumitrescu, S. Astilean and L. I. Gaina, Int. J. Mol. Sci., 2021, 22, 1–21.
A. Pandith, R. G. Siddappa and Y. J. Seo, J. Photochem. Photobiol. C Photochem. Rev., 2019, 40, 81–116.
B. Stoean, L. Gaina, E. Gal, C. Cristea, T. Lovasz and L. Silaghi-Dumitrescu, Stud. Univ. Babes-Bolyai Chem., 2021, 66, 59–66.
V. Talianová, T. Bříza, L. Krčová, B. Dolenský, J. Králová, P. Martásek, V. Král and M. Havlík, Bioorg. Chem., 2020, 94, 103447.
M. M. Corona-López, V. M. Jiménez Pérez, R. Chan-Navarro, M. Ibarra-Rodríguez, H. V. Rasika Dias, A. Chávez-Reyes and B. M. Muñoz-Flores, J. Organomet. Chem., 2017, 852, 64–73.
F. Di Maria, I. E. Palamà, M. Baroncini, A. Barbieri, A. Bongini, R. Bizzarri, G. Gigli and G. Barbarella, Org. Biomol. Chem., 2014, 12, 1603–1610.
L. Gaina, T. Lovasz, I.A. Silberg, C. Cristea, S. Udrea, Het. Commun., 2001, 6, 549–554.
L. Gaina, E. Gal, L. Matarânga-Popa, D. Porumb, A. Nicolescu, C. Cristea, L. Silaghi-Dumitrescu, Tetrahedron, 2012, 68, 2465–2470.
L. Gǎinǎ, C. Cristea, C. Moldovan, D. Porumb, E. Surducan, C. Deleanu, A. Mahamoud, J. Barbe, I.A. Silberg, Int. J. Mol. Sci., 2007, 8, 70–80.
L. Gaina, C. Cristea, I.A. Silberg, T. Lovasz, Rev Roum. Chim, 2002, 47, 983–988.
C. A. Lovasz, T, Oltean, G, Toma, AM, Gaina, L, Silaghi-Dumitrescu, L, Jitaru, M, Cristea, C, Sohar P, Stud. UBB Chem., 2007, 52, 31–38.
L. Gaina, A. Csampai, G. Turos, T. Lovasz, V. Zsoldos-Mady, I.A. Silberg, Org. Biomol. Chem., 2006, 4, 4375–4386.
E. Gál, C. Cristea, L. Silaghi-Dumitrescu, T. Lovász and A. Csámpai, Tetrahedron, 2010, 66, 9938–9944.
L. Gǎinǎ, I. Torje, E. Gal, A. Lupan, C. Bischin, R. Silaghi-Dumitrescu, G. Damian, P. Lönnecke, C. Cristea and L. Silaghi-Dumitrescu, Dye. Pigment., 2014, 102, 315–325.
E. Gal, B. Brem, I. Pereţeanu, L. Gǎinǎ, T. Lovasz, M. Perde-Schrepler, L. Silaghi-Dumitrescu, C. Cristea and L. Silaghi-Dumitrescu, Dye. Pigment., 2013, 99, 144–153.
G. M. Sheldrick, Acta Crystallogr. Sect. A Found. Crystallogr., 2015, 71, 3–8.
G. M. Sheldrick, Acta Crystallogr. Sect. C Struct. Chem., 2015, 71, 3–8.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, J. Appl. Crystallogr., 2009, 42, 339–341.
E. Molnar, E. Gal, L. Gaina, C. Cristea, E. Fischer-Fodor, M. Perde-Schrepler, P. Achimas-Cadariu, M. Focsan and L. Silaghi-Dumitrescu, Int. J. Mol. Sci., 2020, 21, 3178.
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