Synthesis of high conjugated phthalocyanine and porphyrin derivatives: strategies using RMCs and Diels-Alder reactions

• Grant number: 14/24506-3
• Support Opportunities: Scholarships in Brazil - Doctorate
• Start date: May 01, 2015
• End date: February 29, 2020
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Agreement: Coordination of Improvement of Higher Education Personnel (CAPES)
• Principal Investigator: Kleber Thiago de Oliveira
• Grantee: Aloisio de Andrade Bartolomeu
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
• Associated scholarship(s): 18/08772-6 - Direct C-H photocatalyzed arylation of quinolines, pyridines and styrenes with aryldiazonium and diaryliodonium salts, BE.EP.DR

Abstract

Porphyrins and Phthalocyanines are compounds which have been extensively studied as photosensitizers in different areas, including photodynamic therapy (PDT), production of semiconductors, gas sensors, dye-sensitized solar cells, liquid crystals, among other applications. Thus, in this research project, we propose to carry out the synthesis of new phthalocyanine-type photosensitizers starting from high conjugated phthalonitriles obtained from multicomponent reactions (MCRs) in the presence of niobium pentachloride (NbCl5). In a second part of the project, we intend to synthesize two metal tetra-beta-formylporphyrins which will be also employed in MCRs with NbCl5, to obtain high conjugated porphyrin derivatives. The metal tetra-beta-formylporphyrins will also be converted into their respective vinylporphyrins through the Wittig reaction, and then used in the Diels-Alder reactions with maleimides to yield chlorin and bacteriochlorin photosensitizers. Photophysical studies will be performed in order to evaluate the optical properties of the synthetized compounds, aiming at application in solar cells and photonic therapies. (AU)

Scientific publications

(4)

(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)

COSTA E SILVA, RODRIGO; DA SILVA, LUELY OLIVEIRA; BARTOLOMEU, ALOISIO DE ANDRADE; BROCKSOM, TIMOTHY JOHN; DE OLIVEIRA, KLEBER THIAGO. Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches. Beilstein Journal of Organic Chemistry, v. 16, p. 917-955, MAY 6 2020. (18/00106-7, 18/00879-6, 14/24506-3)

BARTOLOMEU, ALOISIO DE A.; BROCKSOM, TIMOTHY J.; DA SILVA FILHO, LUIZ C.; DE OLIVEIRA, KLEBER T.. Multicomponent reactions mediated by NbCl5 for the synthesis of phthalonitrile-quinoline dyads: Methodology, scope, mechanistic insights and applications in phthalocyanine synthesis. DYES AND PIGMENTS, v. 151, p. 391-402, APR 2018. (14/24506-3, 11/13993-2, 13/07276-1, 15/21110-4)

SILVA, TAYNARA L.; BARTOLOMEU, ALOISIO DE A.; DE JESUS, HUGO C. R.; DE OLIVEIRA, KLEBER T.; FERNANDES, JOAO B.; BROMME, DIETER; VIEIRA, PAULO C.. New Synthetic Quinolines as Cathepsin K Inhibitors. Journal of the Brazilian Chemical Society, v. 31, n. 8, p. 1605-1613, AUG 2020. (17/15455-4, 14/24506-3, 18/00106-7, 12/11819-8)

BARTOLOMEU, ALOISIO DE A.; SILVA, RODRIGO C.; BROCKSOM, TIMOTHY J.; NOEL, TIMOTHY; DE OLIVEIRA, KLEBER T.. Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach. Journal of Organic Chemistry, v. 84, n. 16, p. 10459-10471, AUG 16 2019. (13/07276-1, 18/00106-7, 14/24506-3, 18/08772-6, 18/00879-6)