About the synthesis of Naphthalocyanine derivatives: strategies involving organometallic couplings and Methane[10]annulenes

• Grant number: 12/24092-9
• Support type: Scholarships in Brazil - Doctorate
• Effective date (Start): March 01, 2013
• Effective date (End): February 28, 2017
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Kleber Thiago de Oliveira
• Grantee: Nicholas Roberto da Silva Gobo
• Home Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil
• Associated research grant: 08/06619-4 - Synthesis of new photosensitizers with potential aplication in photodynamic therapy, AP.JP

Abstract

The rising application of phthalocyanines in high technology and pharmaceuticals fields has attracted the interest of several research groups around the world. The potential presented by these compounds include: electronic displays, solar cells, storage system, liquid crystals, gas sensors and photodynamic therapy.Thus, in this research project, we intend to accomplish the synthesis of novel photosensitizers aiming at the increasing of conjugations in phthalocyanines through the Heck-Mizoroki cross coupling between allylic esters and halogenated phthalocyanines. The compounds obtained in these cross coupling reactions will yield new naphthalocyanines after electrocyclizations.In a second part of this work, we intended to develop the synthesis of new photosensitizers using 1,6-methano[10]annulenes aiming compounds with an extended conjugation (absorption at 750-1100 nm), and due methylene bridges will provide compounds with low aggregation.Further studies about the potential of these compounds are desired, such as applications in PDT, liquid-crystals and solar cells.

Scientific publications

(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)

DA SILVA GOBO, NICHOLAS ROBERTO; BROCKSOM, TIMOTHY JOHN; DE OLIVEIRA, KLEBER THIAGO. Synthesis of a Naphthalocyanine-Like Dye: The First Report on Zn(II)-1,6-methano[10]annulenecyanine. Molecules, v. 25, n. 9 MAY 2020. Web of Science Citations: 0.

GOBO, NICHOLAS R. S.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T. Soluble and Non-Aggregated Phthalocyanines: Synthesis, Mechanistic Aspects and Their Main Building Blocks. CURRENT ORGANIC SYNTHESIS, v. 14, n. 8, p. 1132-1155, 2017. Web of Science Citations: 1.

PAVANI, CHRISTIANE; FRANCISCO, CLAUDIA M. L.; GOBO, NICHOLAS R. S.; DE OLIVEIRA, KLEBER T.; BAPTISTA, MAURICIO S. Improved photodynamic activity of a dual phthalocyanine-ALA photosensitiser. NEW JOURNAL OF CHEMISTRY, v. 40, n. 11, p. 9666-9671, 2016. Web of Science Citations: 8.