Synthesis of Naphtho-[2,3]-furan derivatives for investigative insights into solvatochromic behaviour

The paper delineates the synthesis of naphtho-[2,3]-furan derivatives (viz. a viz. naphtho-[2,3]-furan-3-yl acetate (NF), 9-nitronaphtho-[2,3]-furan-3-yl acetate (NNF) and 9-bromonaphtho-[2,3-]-furan-3-yl acet-ate (BNF)) using a multistep approach. The products were obtained in high yields and characterized by FT-IR, 1H NMR, 13C NMR, and HRMS spectroscopy. The absorption and fluorescence spectra of these derivatives were recorded in the solvent of different polarities. Solvatochromic correlations were employed to estimate ground state (lg) and excited state (le) dipole moments. The results suggested higher stability of molecules in the singlet excited state than in the ground state. Theoretical investiga-tions indicated that the AEHUMO-LUMO gap varied as AENF> AEBNF >AENNF. The thermogravimetric analysis (TGA) confirmed the higher stability of NNF as compared to BNF and NF.(c) 2023 Elsevier B.V. All rights reserved.

Automated summary

This paper describes the synthesis of naphtho-[2,3]-furan derivatives, including naphtho-[2,3]-furan-3-yl acetate (NF), 9-nitronaphtho-[2,3]-furan-3-yl acetate (NNF), and 9-bromonaphtho-[2,3]-furan-3-yl acetate (BNF), using a multistep approach. The products were characterized by various spectroscopic techniques and their absorption and fluorescence spectra were recorded in different solvents. Solvatochromic correlations were used to estimate dipole moments. Theoretical investigations showed variation in the AEHUMO-LUMO gap. Thermogravimetric analysis confirmed the higher stability of NNF compared to BNF and NF.