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@article{183345,
        author = {Viniket Ramesh Gawand and Ravibabu Tayade and Shreyashi khot and Bharat Raut},
        title = {PHOTOCHROMISM, DFT STUDY, AND SYNTHESIS OF 4-METHOXY CHALCONE FULGIDE AND FULGIMIDE},
        journal = {International Journal of Innovative Research in Technology},
        year = {2025},
        volume = {12},
        number = {3},
        pages = {1380-1386},
        issn = {2349-6002},
        url = {https://ijirt.org/article?manuscript=183345},
        abstract = {Stobbe condensation is a significant reaction for forming carbon-carbon bonds, where aldehydes or ketones are condensed with dimethyl succinate to produce a corresponding acid-ester product.  After the Stobbe condensation, the product undergoes a reaction called ammonolysis to form fulgimide. Substituted chalcone was synthesized using a convenient method to allow further Stobbe condensation reactions. When chalcone, such as (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one, is reacted with dimethyl succinate in the presence of a strong base at room temperature, the corresponding acid-ester product is formed, which is (3Z,5E)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-6-phenylhexa-3,5-dienoic acid. The esterification of this product, followed by another Stobbe condensation with Acetone, gives the acid-ester product (3Z,5E)-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-6-phenyl-2-(propan-2-ylidene) hexa-3,5-dienoic acid. This acid ester product was saponified to give the corresponding diacid, known as fulgenic acid, which is (Z)-2-((E)-1-(4-methoxyphenyl)-3-phenylallylidene)-3-(propan-2-ylidene) succinic acid. Acetylation of the fulgenic acid results in the formation of fulgide, which is (Z)-3-((E)-1-(4-methoxyphenyl)-3-phenylallylidene)-4-(propan-2-ylidene) dihydrofuran-2,5-dione. Further ammonolysis of the fulgide with aniline produces the corresponding fulgimide, (Z)-3-((E)-1-(4-methoxyphenyl)-3-phenylallylidene)-1-phenyl-4-(propan-2-ylidene) pyrrolidine-2,5-dione. Photochromism is the reversible change of color in a material when exposed to light of a certain frequency or intensity. This property makes these materials useful in applications such as optical memory devices, ophthalmic lenses, novelty printing sensors, and more. The fulgide was irradiated at 254 nm wavelength in an immersion-well photochemical reactor to study its photochromic properties. Properties such as bond length, bond angle, dipole moment, HOMO-LUMO gap, and vibrational frequencies were analyzed using Density Functional Theory (DFT) at the B3LYP level with 6- 311+ G** basis set.},
        keywords = {Stobbe condensation, Fulgide, Fulgimide, Photochromism, DFT.},
        month = {August},
        }