Synthesis, Photochemistry, Computational Study and Potential Application of New Styryl-Thiophene and Naphtho-Thiophene Benzylamines

Mlakić, Milena; Odak, Ilijana; Faraho, Ivan; Bosnar, Martina; Banjanac, Mihailo; Lasić, Zlata; Marinić, Željko; Barić, Danijela; Škorić, Irena (2022) Synthesis, Photochemistry, Computational Study and Potential Application of New Styryl-Thiophene and Naphtho-Thiophene Benzylamines. International Journal of Molecular Sciences, 24 (1). ISSN 1422-0067

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Abstract

In this research, the synthesis, photochemistry, and computational study of new cis- and trans-isomers of amino-thienostilbenes is performed to test the efficiency of their production and acid resistance, and to investigate their electronic structure, photoreactivity, photophysical characteristics, and potential biological activity. The electronic structure and conformations of synthesized thienostilbene amines and their photocyclization products are examined computationally, along with molecular modeling of amines possessing two thiophene rings that showed inhibitory potential toward cholinesterases. New amino-styryl thiophenes, with favorable photophysical properties and proven acid resistance, represent model compounds for their water-soluble ammonium salts as potential styryl optical dyes. The comparison with organic dyes possessing a trans-aminostilbene subunit as the scaffold shows that the newly synthesized trans-aminostilbenes have very similar absorbance wavelengths. Furthermore, their functionalized cis-isomers and photocyclization products are good candidates for cholinesterase inhibitors because of the structural similarity of the molecular skeleton to some already proven bioactive derivatives.

Item Type:	Article
Uncontrolled Keywords:	acid resistance; benzylamines; DFT; heterostilbenes; molecular docking; photocyclization; semiempirical methods; TD-DFT
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	NMR Center
Depositing User:	Danijela Barić
Date Deposited:	23 Apr 2026 14:16
URI:	https://fulir.irb.hr:/id/eprint/11788
DOI:	10.3390/ijms24010610

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