Optical Properties and Tautomerism of 2-Carbamido-1,3-Indandione in Ground and Excited States

IF 3.4 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Journal of Computational Chemistry Pub Date : 2025-03-03 DOI:10.1002/jcc.70041

Venelin Enchev, Tsvetan Zahariev, Nina Stoyanova, Ivan Angelov, Ivelina Georgieva

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Abstract

2-Carbamido-1,3-indanedione (CAID) is a fluorescent compound, existing in two tautomeric forms: A and B. Spectroscopic features of CAID suggest that the tautomeric equilibrium is possible both in ground and excited state. To further elucidate this, measurements of UV–Vis absorption and fluorescence spectra were recorded in various solvents. The ground and low-lying excited states of CAID are modeled at SOS-MP2/ADC(2) computational level. The two tautomers A and B coexist in ground state with the amount of A amounting to 90% and a dynamic equilibrium is established. However, in all excited states the tautomer B is more stable and its amount is almost 100%. Along with fluorescence from the first excited state of both tautomers, a rare case of breaking Kasha's rule—fluorescence from the third excited state of the two tautomers—has been observed. A scheme is proposed to explain the photophysical processes and photoreactions of CAID in ethanol solution.

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来源期刊

Journal of Computational Chemistry 化学-化学综合

CiteScore

6.60

自引率

3.30%

发文量

247

审稿时长

1.7 months

期刊介绍： This distinguished journal publishes articles concerned with all aspects of computational chemistry: analytical, biological, inorganic, organic, physical, and materials. The Journal of Computational Chemistry presents original research, contemporary developments in theory and methodology, and state-of-the-art applications. Computational areas that are featured in the journal include ab initio and semiempirical quantum mechanics, density functional theory, molecular mechanics, molecular dynamics, statistical mechanics, cheminformatics, biomolecular structure prediction, molecular design, and bioinformatics.