Study about the one-pot synthesis and application as organic dyes of quinolone and anthrazoline derivatives

• Grant number: 18/14506-7
• Support Opportunities: Regular Research Grants
• Start date: December 01, 2018
• End date: November 30, 2020
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Luiz Carlos da Silva Filho
• Grantee: Luiz Carlos da Silva Filho
• Host Institution: Faculdade de Ciências (FC). Universidade Estadual Paulista (UNESP). Campus de Bauru. Bauru , SP, Brazil

Abstract

In recent years the aza-heterocyclic conjugated compounds, such as quinolines and anthrazolines derivatives, have gained interest in the scientific community due to the diversified electronic properties that allow for a wide range of optoelectronic applications (e.g., sensors, metal corrosion inhibitors, photopolymerization initiators, OLEDs, DSSCs (dye-sensitized solar cells) and perovskite solar cells (CSP)). While there are many potential applications for these compounds, synthetic methods are costly and require multiple steps, which may prevent widespread application on a commercial scale. Specifically, we are looking to decrease the production cost and improve synthetic ease for this class of materials (e.g., reducing processes of separation and purification of these compounds). Among the methodologies widely used in organic synthesis, multicomponent reactions (RMCs) are essential. This process involves three or more reactants added to the reaction system, leading to the formation of a product containing the structural characteristics of each of the reagents used, highly advantageous compared to multi-step synthesis. RMCs can also be classified as one-pot reactions, where the sequences of reactions in which a previous transformation makes the obtained species reactive to another reagent that is also present in the reactional medium, followed by formation of the expected final product, without needing to perform product separations at each step and neither purification. In the synthesis of the various aza-heterocyclic derivatives, the use of catalysts is extremely important, also with the objective of increasing reaction yields and reducing working times, thus reducing production costs. In this sense, our research group has regularly presented excellent results of the application of NbCl5 in different RMCs. Hence, in this research project, it is proposed to study the use of NbCl5 not only with one-pot reaction agent to obtain quinoline and anthrazoline derivatives through sequential RMCs, as well as its application as a reducing agent NO2 groups through the formation of complexes with metals, such as Zn and Nb. It is also intended to study the different possibilities of application of the proposed compounds, such as: chemosensors, photoinitiators of polymerization reactions, anti-corrosive agents and hole transport materials in CSP and OLEDs. (AU)

Scientific publications

(16)

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

ALARCON, RAFAEL TURRA; GAGLIERI, CAROLINE; DOS SANTOS, GIOVANNY CARVALHO; ROLDAO, JUAN CARLOS; MAGDALENA, AROLDO GERALDO; DA SILVA-FILHO, LUIZ CARLOS; BANNACH, GILBERT. A deep investigation into the thermal degradation of urethane dimethacrylate polymer. JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, APR 2021. (18/03460-6, 15/00615-0, 16/01599-1, 17/08820-8, 18/14506-7)

ALARCON, RAFAEL TURRA; GAGLIERI, CAROLINE; DOS SANTOS, GIOVANNY CARVALHO; ROLDAO, JUAN CARLOS; MAGDALENA, AROLDO GERALDO; DA SILVA-FILHO, LUIZ CARLOS; BANNACH, GILBERT. A deep investigation into the thermal degradation of urethane dimethacrylate polymer. JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, v. 147, n. 4, p. 3083-3097, FEB 2022. (16/01599-1, 17/08820-8, 18/03460-6, 18/14506-7, 15/00615-0)

DE MOURA, ANIELE; GAGLIERI, CAROLINE; DA SILVA-FILHO, LUIZ CARLOS; CAIRES, FLAVIO JUNIOR. Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative. JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, v. 146, n. 2, p. 587-594, OCT 2021. (18/24378-6, 18/14506-7, 13/07296-2)

MARTINS, LUCAS MICHELAO; BREGADIOLLI, BRUNA ANDRESSA; AUGUSTO, LAIS CRISTINA; LAZARO DE CARVALHO, JOSE HENRIQUE; ZAGHETE, MARIA APARECIDA; DA SILVA FILHO, LUIZ CARLOS. Synthesis of Novel 1,4-dihydro-1,2,4,5-tetraarylpyrrolo[3,2-b]pyrroles Derivatives Catalyzed by NbCl5 and Application in Dye Sensitized Solar Cells. MATERIALS RESEARCH-IBERO-AMERICAN JOURNAL OF MATERIALS, v. 24, n. 1, 2021. (16/01599-1, 18/14506-7, 18/09235-4, 17/07627-0)

DOS SANTOS, GIOVANNY CARVALHO; MARTINS, LUCAS MICHELAO; BREGADIOLLI, BRUNA ANDRESSA; MORENO, VITOR FERNANDES; DA SILVA-FILHO, LUIZ CARLOS; SACOMAN TORQUATO DA SILVA, BRUNO HENRIQUE. Heterocyclic compounds as antiviral drugs: Synthesis, structure-activity relationship and traditional applications. Journal of Heterocyclic Chemistry, v. 58, n. 12, AUG 2021. (18/14506-7, 18/09235-4, 17/07627-0)

GIOVANNY C. DOS SANTOS; JULIA L. RODRIGUES; JÚLLIA R. DE SOUZA; LUIZ C. DA SILVA-FILHO; BRUNO H. S. T. DA SILVA. A QUÍMICA POR TRÁS DOS MEDICAMENTOS DISTRIBUÍDOS PELO PROGRAMA FARMÁCIA POPULAR NO BRASIL: ROTAS SINTÉTICAS, RELAÇÃO ESTRUTURA-ATIVIDADE E PERSPECTIVAS FUTURAS. Química Nova, v. 44, n. 10, p. 1280-1299, 2021-12-20. (18/14506-7, 15/00615-0, 18/10112-4)

MARTINS, LUCAS MICHELAO; MORENO, VITOR FERNANDES; ROSARIO, ILANA SGANZERLA; DE OLIVEIRA GRAEFF, CARLOS FREDERICO; SILVA FILHO, LUIZ CARLOS. Bronsted Acid Mediated Facile Greener Multicomponent Synthesis of 2,4-Diaryl-quinoline Derivatives in Water. ORBITAL-THE ELECTRONIC JOURNAL OF CHEMISTRY, v. 14, n. 1, p. 9-pg., 2021-01-01. (13/07296-2, 18/14506-7, 16/01599-1, 18/09235-4)

PAVAN, NATHALIA MARIANA; MARTINS, LUCAS MICHELAO; AUGUSTO, LAIS CRISTINA; DA SILVA-FILHO, LUIZ CARLOS; XIMENES, VALDECIR FARIAS. Development of fluorescent azapentalenes to study the reactivity of hypochlorous acid and chloramines in micellar systems. JOURNAL OF MOLECULAR LIQUIDS, v. 365, p. 10-pg., 2022-08-27. (18/14506-7, 19/18445-5)

ALARCON, RAFAEL TURRA; DOS SANTOS, GIOVANNY CARVALHO; DE OLIVEIRA, ARTHUR ROSSI; DA SILVA-FILHO, LUIZ CARLOS; BANNACH, GILBERT. Synthesis of luminescent polymers in the UV light region from dimethacrylate monomer using novel quinoline dyes. Journal of Applied Polymer Science, v. 136, n. 19, MAY 15 2019. (13/09022-7, 18/03460-6, 16/01599-1, 18/14506-7, 15/00615-0, 17/08820-8)

DE MOURA, ANIELE; GAGLIERI, CAROLINE; ALARCON, RAFAEL TURRA; FERREIRA, LAURA TEOFILO; VECCHI, RAFAEL; ROVIS SANCHES, MARIANA LIESSA; DE OLIVEIRA, RODRIGO CARDOSO; VENTURINI, JAMES; DA SILVA-FILHO, LUIZ CARLOS; CAIRES, FLAVIO JUNIOR. A New Curcuminoids-Coumarin Derivative: Mechanochemical Synthesis, Characterization and Evaluation of Its In Vitro Cytotoxicity and Antimicrobial Properties. CHEMISTRYSELECT, v. 6, n. 41, p. 11352-11361, NOV 8 2021. (13/07296-2, 18/03460-6, 18/14506-7, 18/24378-6)

DOS SANTOS, GIOVANNY CARVALHO; ROLDAO, JUAN CARLOS; SHI, JUNQING; MILIAN-MEDINA, BEGONA; DA SILVA-FILHO, LUIZ CARLOS; GIERSCHNER, JOHANNES. 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. ChemPhysChem, v. 21, n. 16, JUL 2020. (18/14506-7, 18/10112-4, 15/00615-0)

DOS SANTOS, GIOVANNY CARVALHO; RODRIGUES, JULIA LOPES; MORENO, VITOR FERNANDES; DA SILVA-FILHO, LUIZ CARLOS. Environmental effects in nitroquinoline derivatives solutions: Solvatochromism, acid-base effect and ion-sensor investigation. Journal of Molecular Structure, v. 1235, p. 8-pg., 2021-03-19. (18/14506-7, 15/00615-0, 16/01599-1)

DE MOURA, ANIELE; GAGLIERI, CAROLINE; DA SILVA-FILHO, LUIZ CARLOS; CAIRES, FLAVIO JUNIOR. Mechanochemical synthesis, characterization and thermoanalytical study of a new curcumin derivative. JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, JUL 2020. (18/24378-6, 13/07296-2, 18/14506-7)

DOS SANTOS, GIOVANNY CARVALHO; MORENO, VITOR FERNANDES; OSHIRO, PAULA BEATRIZ; DA SILVA-FILHO, LUIZ CARLOS. NbCl5 a multifunctional reagent for the synthesis of new halogenated aminoquinoline compounds through innovative one-pot reaction and the acidochromism effect. Tetrahedron, v. 74, n. 42, p. 6144-6149, OCT 18 2018. (12/24199-8, 15/00615-0, 18/14506-7, 16/01599-1)

PASTRELLO, BRUNA; DOS SANTOS, GIOVANNY CARVALHO; DA SILVA-FILHO, LUIZ CARLOS; DE SOUZA, AGUINALDO ROBINSON; MORGON, NELSON HENRIQUE; XIMENES, VALDECIR FARIAS. Novel aminoquinoline-based solvatochromic fluorescence probe: Interaction with albumin, lysozyme and characterization of amyloid fibrils. DYES AND PIGMENTS, v. 173, FEB 2020. (15/00615-0, 15/22338-9, 16/20549-5, 18/14506-7, 14/50926-0)

DOS SANTOS, GIOVANNY CARVALHO; MORENO, VITOR FERNANDES; SACOMAN TORQUATO DA SILVA, BRUNO HENRIQUE; DA SILVA-FILHO, LUIZ CARLOS. Heterocyclic anthrazoline derivatives: a critical review. NEW JOURNAL OF CHEMISTRY, v. 43, n. 47, p. 18415-18432, DEC 21 2019. (15/00615-0, 18/14506-7)