Theoretical-Experimental Photophysical Investigations of the Solvent Effect on the Properties of Green- and Blue-Light-Emitting Quinoline Derivatives

Abstract

This paper describes the investigations on the solvatochromic effect and the photophysical properties of quinoline derivatives, compounds with potential applicability in optoelectronic devices. Using an experimental and theoretical approach, the effect of the solvent and the insertion of the phenyl, nitro, amino and dimethylamino group in the quinoline backbone were investigated. The use of Density Functional Theory (DFT) calculations provided the bases for the understanding of the energetic transitions observed in the absorption and fluorescence experiments. In general, it was observed a change in the wavelength of maximum absorption and fluorescence quantum yield of the studied compounds caused by the substituents in the quinoline core. This effect was correlated with the solvent dielectric constants.

Synthesis of Green/Blue Light Emitting Quinolines by Aza-D-A Reaction Using InCl3 Catalyst

“…To examine the efficacy of InCl 3 extensive comparative studies with several catalytic systems have been investigated. Thus, several reactions were scrutinized in the presence of catalysts like InBr 3 , AlCl 3 , FeCl 3, Cu(OTf) 2, CuCl 2, CAN, I 2, TFA, p-TsOH and BF 3 OEt 3 , respectively ( Table 1, entries [11][12][13][14][15][16][17][18][19][20]. All the tested acids gaive lower yields than that of InCl 3 , however, in the case of Cu(OTf) 2 , a mixture of compounds are observed.…”

“…1). In addition to bioactivity, quinolines scaffolds also show luminescent properties with potential applications in organic solar cells (OSCs), organic light emitting diodes (OLEDs), biomolecular markers, molecular probes and switches [12][13][14]. Moreover, quinoline-based dyes such as ethyl red iodide and pinacyanol ( Fig.…”

Exploring the effect of different coumarin donors on the optical and photovoltaic properties of azo‐bridged push‐pull systems: A theoretical approach

“…Moreover, DFT provides a range of functionals and amongst these, B3LYP has been found as a reliable functional for the determination of optical, electronic, as well as structural properties of small‐ to medium‐sized organic molecules . The results obtained, after benchmark tests based on experimental and theoretical data for various functionals, have shown that the results obtained with B3LYP are generally in good agreement with the corresponding experimental values …”

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

“…[29] Introducing amino-and nitro-functionalities as donor and acceptor groups, respectively, the optical and photophysical response can be drastically altered, while keeping the fundamental molecular backbone. [30][31] Moreover, strong solvatochromic effects were observed for this class of compounds; [26,[32][33] and for some derivatives dual emission was observed. [34][35][36][37] The basicity of the chromophores can be tuned, so that large variations in the pH response of quinolines are observed.…”