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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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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dos Santos, Giovanny Carvalho [1, 2] ; Roldao, Juan Carlos [2] ; Shi, Junqing [2, 3] ; Milian-Medina, Begona [4] ; da Silva-Filho, Luiz Carlos [1] ; Gierschner, Johannes [2]
Total Authors: 6
[1] Sao Paulo State Univ UNESP, Lab Organ Synth & Proc LOSP, Dept Chem, Sch Sci, BR-17033360 Bauru, SP - Brazil
[2] IMDEA Nanociencia, Ciudad Univ Cantoblanco, C Faraday 9, Madrid 28049 - Spain
[3] Northwestern Polytech Univ, Xian Inst Flexible Elect, Dongxiang St 1, Xian 710072, Shaanxi - Peoples R China
[4] Univ Valencia, Fac Chem, Dept Phys Chem, Ave Dr Moliner 50, Burjassot 46100, Valencia - Spain
Total Affiliations: 4
Document type: Journal article
Source: ChemPhysChem; v. 21, n. 16 JUL 2020.
Web of Science Citations: 0

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-pi{*} and pi pi{*} 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. (AU)

FAPESP's process: 18/14506-7 - Study about the one-pot synthesis and application as organic dyes of quinolone and anthrazoline derivatives
Grantee:Luiz Carlos da Silva Filho
Support type: Regular Research Grants
FAPESP's process: 18/10112-4 - "Studies on the synthesis and photochemical and photophysical characterization of quinoline derivatives with donor-Pi-acceptor structure for use as sensitizing dyes of organic electronic devices"
Grantee:Giovanny Carvalho dos Santos
Support type: Scholarships abroad - Research Internship - Doctorate
FAPESP's process: 15/00615-0 - Studies on the synthesis and photochemical and photophysical characterization of quinoline derivatives with donor-p-acceptor structure for use as sensitizing dyes in organic electronic devices
Grantee:Giovanny Carvalho dos Santos
Support type: Scholarships in Brazil - Doctorate