Studies about the use of NbCl5 in multicomponent reactions for the synthesis of organic dyes

• Grant number: 16/01599-1
• Support Opportunities: Regular Research Grants
• Start date: May 01, 2016
• End date: April 30, 2018
• 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

The development of organic electronic devices have received great prominence in the global scientific scene, because those devices have a low cost for their production and present a good conversion efficiency of solar energy into electrical energy, electrical energy into light energy, amplification of electrical signals, among others. The main applications of organic compounds in electronic devices include: organic dye-sensitize solar cells (DSSCs), organic light emitting devices (OLEDs), organic field effect transistors (OFETs), flexible information displays, radio-frequency identification cards (RFID), textile and sensing electronics. Because of this, the synthetic organic chemistry emerges as an excellent tool for the development of sensitizing dyes in organic electronic devices, allowing the synthesis of new types of dyes and also granting through structural changes in organic dyes already used, the potentiation thereof. Therefore, in this project we propose to conduct a study for obtaining the differents tetra-aryl-1,4-dihydro-pyrrol[3,2-b]pyrrole and xanthene derivatives through multicomponent reactions promoted by niobium pentachloride (NbCl5), by checking in detail the effect of the concentration of NbCl5 in the reaction time and yield of the formed products. After preparation of the compounds of interest, they will be submitted to structural, photochemical and photophysical analyses, so that we can enable their application as sensitizing dyes in organic electronic devices (DSSCs and OLEDs). It is also intended to inquire what the effect of the substituent groups are, being them donors or withdrawing of electrons, in proportion and yield of the formed products, in the reaction times and in the physical and chemical properties of the formed products. (AU)

Scientific publications

(21)

(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)

MARTINS, JEFFERSON S.; BARTOLOMEU, ALOISIO A.; DOS SANTOS, WILLIAN HENRIQUE; DA SILVA FILHO, LUIZ CARLOS; DE OLIVEIRA, ELIEZER FERNANDO; LAVARDA, FRANCISCO CARLOS; CUIN, ALEXANDRE; LEGNANI, CRISTIANO; MACIEL, INDHIRA O.; FRAGNEAUD, BENJAMIN; et al. New Class of Organic Hole-Transporting Materials Based on Xanthene Derivatives for Organic Electronic Applications. Journal of Physical Chemistry C, v. 121, n. 24, p. 12999-13007, JUN 22 2017. (13/08697-0, 14/20410-1, 16/01599-1, 12/21983-0, 12/23821-7)

SACOMAN TORQUATO DA SILVA, BRUNO HENRIQUE; BREGADIOLLI, BRUNA ANDRESSA; DE OLIVEIRA GRAEFF, CARLOS FREDERICO; DA SILVA-FILHO, LUIZ CARLOS. NbCl5-Promoted Synthesis of Fluorescein Dye Derivatives: Spectroscopic and Spectrometric Characterization and Their Application in Dye-Sensitized Solar Cells. CHEMPLUSCHEM, v. 82, n. 2, p. 261-269, FEB 2017. (14/01337-1, 11/02205-3, 16/01599-1)

DOS SANTOS, WILLIAN HENRIQUE; DA SILVA-FILHO, LUIZ CARLOS. New method for the synthesis of chromeno[4,3-b]chromene derivatives via multicomponent reaction promoted by niobium pentachloride. Tetrahedron Letters, v. 58, n. 9, p. 894-897, MAR 1 2017. (16/01599-1)

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)

DOS SANTOS, GIOVANNY CARVALHO; SERVILHA, ROBERTA OLIVEIRA; DE OLIVEIRA, ELIZER FERNANDO; LAVARDA, FRANCISCO CARLOS; XIMENES, VALDECIR FARIAS; DA SILVA-FILHO, LUIZ CARLOS. Theoretical-Experimental Photophysical Investigations of the Solvent Effect on the Properties of Green- and Blue-Light-Emitting Quinoline Derivatives. Journal of Fluorescence, v. 27, n. 5, p. 1709-1720, SEP 2017. (13/08697-0, 15/00615-0, 14/20410-1, 16/01599-1, 12/21983-0, 12/24199-8)

DANIEL B. FUMIS; MARIA L.D.C SILVEIRA; CAROLINE GAGLIERI; LAURA T. FERREIRA; RODRIGO F.C. MARQUES; AROLDO G. MAGDALENA. The Effect of EDTA Functionalization on Fe3O4 Thermal Behavior. MATERIALS RESEARCH-IBERO-AMERICAN JOURNAL OF MATERIALS, v. 25, 2022-10-28. (16/01599-1, 13/09022-7, 15/00615-0)

MORENO, VITOR FERNANDES; DOS SANTOS, GIOVANNY CARVALHO; GASPAR DA COSTA, GYORDANNA MAYARA; AYALA GOMES, MARCELO HENRIQUE; DA SILVA-FILHO, LUIZ CARLOS. NbCl5 Promoted the Efficient Synthesis of Phthalein Derivatives: Optical Characterization and Solvatochromic Effect. Journal of Heterocyclic Chemistry, v. 56, n. 10, AUG 2019. (12/24199-8, 16/01599-1, 15/00615-0)

MARTINS, LUCAS MICHELAO; VIEIRA, SAMUEL DE FARIA; BALDACIM, GABRIEL BALDO; BREGADIOLLI, BRUNA ANDRESSA; CARASCHI, JOSE CLAUDIO; BATAGIN-NETO, AUGUSTO; DA SILVA-FILHO, LUIZ CARLOS. Improved synthesis of tetraary1-1,4-dihydropyrrolo[3,2-b]pyrroles a promising dye for organic electronic devices: An experimental and theoretical approach. DYES AND PIGMENTS, v. 148, p. 81-90, JAN 2018. (16/01599-1)

DOS SANTOS, GIOVANNY CARVALHO; OLIVEIRA, ELIEZER FERNANDO; LAVARDA, FRANCISCO CARLOS; DA SILVA-FILHO, LUIZ CARLOS. Designing new quinoline-based organic photosensitizers for dye-sensitized solar cells (DSSC): a theoretical investigation. Journal of Molecular Modeling, v. 25, n. 3, MAR 2019. (13/08697-0, 15/00615-0, 14/20410-1, 16/01599-1, 16/18499-0, 12/21983-0, 12/24199-8)

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)

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)

SACOMAN TORQUATO DA SILVA, BRUNO HENRIQUE; RIEHL, LUIZA OLBERA; DOS SANTOS, GIOVANNY CARVALHO; ROLDAO, JUAN CARLOS; DA SILVA-FILHO, LUIZ CARLOS. Solvent-Free Synthesis Using Nb2O5 and a Theoretical-Experimental Study of Solvent Effect in New Rhodamine Dyes. CHEMISTRYSELECT, v. 5, n. 4, p. 1455-1463, JAN 31 2020. (14/01337-1, 16/01599-1, 15/00615-0)

BALDO PIRES, OSMAR ANTONIO; ALARCON, RAFAEL TURRA; GAGLIERI, CAROLINE; DA SILVA-FILHO, LUIZ CARLOS; BANNACH, GILBERT. Synthesis and characterization of a biopolymer of glycerol and macadamia oil. JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, v. 137, n. 1, p. 161-170, JUL 2019. (17/08820-8, 15/00615-0, 16/01599-1, 18/03460-6, 13/09022-7)

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)

LAZARO DE CARVALHO, JOSE HENRIQUE; BREGADIOLLI, BRUNA ANDRESSA; DA SILVA-FILHO, LUIZ CARLOS. Niobium Compounds in Transesterification Reactions of Soybean Oil: A Promising Use of NbCl5. ORBITAL-THE ELECTRONIC JOURNAL OF CHEMISTRY, v. 10, n. 5, p. 423-429, APR-JUN 2018. (16/01599-1)

SIQUEIRA, MAYARA DE SOUZA; DA SILVA-FILHO, LUIZ CARLOS. NbCl5-promoted the synthesis of 4H-pyrans through multicomponent reaction. Tetrahedron Letters, v. 57, n. 46, p. 5050-5052, NOV 16 2016. (16/01599-1)

ALARCON, RAFAEL TURRA; GAGLIERI, CAROLINE; SACOMAN TORQUATO DA SILVA, BRUNO HENRIQUE; DA SILVA FILHO, LUIZ CARLOS; BANNACH, GILBERT. New fluorescein dye derivatives and their use as an efficient photoiniator using blue light LED. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, v. 343, p. 112-118, JUN 15 2017. (12/21450-1, 14/01337-1, 13/09022-7, 16/01599-1)

DOS SANTOS, WILLIAN HENRIQUE; DE OLIVEIRA, ELIEZER FERNANDO; LAVARDA, FRANCISCO CARLOS; LEONARCZYK, IVES ANTONIO; BARBOSA FERREIRA, MARCO ANTONIO; DA SILVA-FILHO, LUIZ CARLOS. One-Step Synthesis of Methoxylated Phloroglucinol Derivatives Promoted by Niobium Pentachloride: An Experimental and Theoretical Approach. SYNTHESIS-STUTTGART, v. 49, n. 11, p. 2402-2410, JUN 2017. (15/08541-6, 16/01599-1, 12/21983-0, 14/20410-1)

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)

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; 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)