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RESEARCH PRODUCT

Combined Spectroscopic and TD-DFT Analysis to Elucidate Substituent and Acidochromic Effects in Organic Dyes: A Case Study on Amino- versus Nitro-Substituted 2,4-Diphenylquinolines

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Made available in DSpace on 2020-12-12T01:33:30Z (GMT). No. of bitstreams: 0 Previous issue date: 2020-01-01 A combined spectroscopic and TD-DFT case study was performed, to identify a robust method to calculate the complex near UV/Vis absorption spectra of various amino- vs. nitro-substituted 2,4-diphenylquinolines, which vary strongly under neutral and successively acidic conditions. For this, different DFT functionals were tested for geometry optimization and the TD part to calculate the neutral and different protonated species in a fast screening approach, i. e. using single point calculations in an implicit solvent. Offset-corrected M06HF, hitherto only applied to polymers, was identified as a suitable method to reproduce the absorption spectra in a reasonable fashion for all different substitution pattern and all different protonated species at different pH values; moreover, the method properly predicts the energetic ordering of low-lying n-π* and ππ* transitions, which is decisive for the non-/emissive nature of the different compounds. In all, this might provide a valuable tool for computer-aided design of related classes of compounds. Laboratory of Organic Synthesis and Processes (LOSP) São Paulo State University (UNESP) Department of Chemistry School of Sciences IMDEA Nanociencia Ciudad Universitaria de Cantoblanco, C/ Faraday 9 Xi'an Institute of Flexible Electronics Northwestern Polytechnical University Dongda Town, Dongxiang Street 1 Department for Physical Chemistry Faculty of Chemistry University of Valencia, Avenida Dr. Moliner 50 Laboratory of Organic Synthesis and Processes (LOSP) São Paulo State University (UNESP) Department of Chemistry School of Sciences