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Facile Synthesis and Photophysical Characterization of New Quinoline Dyes

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Abstract

This paper describes the synthesis of new quinoline derivatives, molecules that has been long interest in the organic and medicinal chemistry. Through the Multicomponent Reaction (MCR), an important tool in modern synthetic methodology, that generate products with good structural complexity, in addition to economy of atoms and selectivity, we provide easy access to the preparation of quinoline derivatives. The reactions were promoted by niobium pentachloride, as a Lewis acid. Subsequently, the synthesis of new aminoquinoline derivatives with good yields was performed using Pd/C and hydrazine. The photophysical investigations of quinoline derivatives show the substituent effect on the optical properties characterization was done by absorption and photoluminescence measurements with quantum yields of up to 83 %, the presence of the amino group at position 6 at the quinoline backbone was crucial for obtaining these increased quantum yields. Results show that these molecules may have potential use for a variety of applications and mainly attracts attention because of its wide potential of applicability in optoelectronic devices.

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Acknowledgments

The authors would like to thank Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) (Procs. 2013/08,697–0, 2012/24,199–8, 2015/00,615–0 and 2016/01,599–1), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) (Proc. 302,753/2015–0) and Pró-Reitoria de Pesquisa (PROPe-UNESP) for their financial support. We would also like to thank CBMM – Companhia Brasileira de Mineralogia e Mineração for the NbCl5 samples. We express our special thanks to N. P. Lopes, J. N. Mendonça and J. C. Tomaz at the University of São Paulo in Ribeirão Preto for the HRMS analyses.

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  1. Laboratory of Organic Synthesis and Processes (LOSP), Department of Chemistry, Faculty of Sciences, São Paulo State University (UNESP), 17033-360, Bauru, São Paulo, Brazil

    Giovanny Carvalho dos Santos, Aloisio de Andrade Bartolomeu, Valdecir Farias Ximenes & Luiz Carlos da Silva-Filho

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  1. Giovanny Carvalho dos Santos
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Santos, G.C.d., de Andrade Bartolomeu, A., Ximenes, V.F. et al. Facile Synthesis and Photophysical Characterization of New Quinoline Dyes. J Fluoresc 27, 271–280 (2017). https://doi.org/10.1007/s10895-016-1954-5

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