Predicting the modulation of UV–vis absorption and emission of mono-substituted pyrido[2,3,4-kl]acridines by electronic density variations analysis

• Published in: Computational and theoretical chemistry Vol. 1213; p. 113733
• Main Authors: Tiano, Martin, Courdurié, Chloé, Colinet, Pauline
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.07.2022; Elsevier
• Subjects: Chemical Sciences; Coordination chemistry; Education; Electronic density; Hammett parameter; Humanities and Social Sciences; Material chemistry; Organic chemistry; Pyrido[2,3,4-kl]acridine; TD-DFT; UV–Visible spectroscopy; EDP; Hammett parameter; EWG; UV–Visible spectroscopy; Electronic density; Pyrido[2,3,4-kl]acridine; GS; ES; TD-DFT
• ISSN: 2210-271X; 2210-2728
• DOI: 10.1016/j.comptc.2022.113733

[Display omitted] •Pyrido[2,3,4-kl]acridines exhibit biological activities and fluorescent properties.•(TD)-DFT calculations accurately simulate UV–Visible absorptions and emissions of pyrido[2,3,4-kl]acridine.•Transition energies correlate with electronic density variation between the ground and the excited states.•Hammett parameter indicates accurately the influence of a substituent on spectroscopic properties.•The best substitution positions and the best substituents is achievable by extrapolation. DFT and TD-DFT calculations were performed to rationalize the link between UV–Visible absorption and emission spectra and the nature and position of a substituent on the heteroaromatic pyrido[2,3,4-kl]acridine skeleton. By studying the variation of electronic density and atomic partial charges between the ground state and the first excited state, we describe here a quantitative protocol to predict the modulation of UV–Visible spectroscopic properties depending on the nature and the position of a substituent.