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Cross-coupling reactions on the synthesis of new photosensitizers with high conjugation

Grant number: 13/06532-4
Support type:Regular Research Grants
Duration: July 01, 2013 - June 30, 2015
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Kleber Thiago de Oliveira
Grantee:Kleber Thiago de Oliveira
Home Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

This project aims at the synthesis of new porphyrins and phthalocyanines derivatives with high conjugation, more specifically dibenzobacteriochlorins and naphthalocyanines. Therefore, we are proposing a linear synthesis of some bacteriochlorins and phthalocyanines, both adequately substituted with halogens for further functionalization through the organometallic cross-couplings. The coupling products will be submitted to the electrocyclization/aromatization reactions, in order to obtain the desired dibenzobacteriochlorins and naphthalocyanines. These studies intended to cover the aspects of methodology on the use of organometallic cross-couplings in photosensitizers, besides to study electrocyclization/aromatization reactions as a general strategy for the production of photosensitizers with high conjugation level (current focus of our group). It is expected to obtain structures of new photosensitizers named here dibenzobacteriochlorins, whose photophysical properties can be promising for application under numerous perspectives. Specifically in the studies on organometallic cross-coupling with halophthalocyanines should be noted that, until this date, this strategy has not been used for the production of naphthalocyanines. Thus, it can be considered an important contribution from the methodological point of view. Also, the properties of these new compounds can point to applications in numerous areas such as photonic therapies, fluorescent markers, OLEDs, liquid crystals, and others.More broadly, we intend to move forward with this project that is related to the research initiated in 2009 (Young Researcher Financial Support 2008/06619-4) - Synthesis of Heterocyclic Compounds with Photosensitizing Activities). Currently, we have 4 PhD students, 2 master's degree, 3 ICs and 2 postdocs in our group working on different fronts of our research line. We established our team at the UFSCar just over 2 ½ years and, since then our team has grown significantly and, with it the consumption needs, equipment and infrastructure to conduct our research. The young researcher financial support from FAPESP assisted us with the major requirements to start up our group. Now, we inevitably need to invest in the infrastructure of the laboratory, adapting and reforming it as soon as possible. Also, we need to maintain the current researches in terms of budgets. (AU)

Scientific publications (13)
(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)
DONATONI, MARIA C.; VIEIRA, YGOR W.; BROCKSOM, TIMOTHY J.; RABELO, ADRIANO C.; LEITE, EDSON R.; DE OLIVEIRA, KLEBER T. One-pot sequential functionalizations of meso-tetrathienylporphyrins via Heck-Mizoroki cross-coupling reactions. Tetrahedron Letters, v. 57, n. 27-28, p. 3016-3020, JUL 6 2016. Web of Science Citations: 4.
DE ASSIS, FRANCISCO F.; FERREIRA, MARCO A. B.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T. NIR bacteriochlorin chromophores accessed by Heck and Sonogashira cross-coupling reactions on a tetrabromobacteriochlorin derivative. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 14, n. 4, p. 1402-1412, 2016. Web of Science Citations: 8.
DE OLIVEIRA, KLEBER T.; MILLER, L. ZANE; MCQUADE, D. TYLER. Exploiting photooxygenations mediated by porphyrinoid photocatalysts under continuous flow conditions. RSC ADVANCES, v. 6, n. 16, p. 12717-12725, 2016. Web of Science Citations: 13.
RAMOS, L. D.; SAMPAIO, R. N.; DE ASSIS, F. F.; DE OLIVEIRA, K. T.; HOMEM-DE-MELLO, P.; PATROCINIO, A. O. T.; FRIN, K. P. M. Contrasting photophysical properties of rhenium(I) tricarbonyl complexes having carbazole groups attached to the polypyridine ligand. DALTON TRANSACTIONS, v. 45, n. 29, p. 11688-11698, 2016. Web of Science Citations: 13.
MOMO, PATRICIA B.; SAMPAIO, OLIVIA M.; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T. Selective Vilsmeier-Haack aryl-formylations of tetrathienylporphyrin and its Ni(II) complex. Journal of Porphyrins and Phthalocyanines, v. 19, n. 6, p. 745-752, JUN 2015. Web of Science Citations: 1.
ALVES, LEANDRO DE C.; DESIDERA, ANDRE L.; DE OLIVEIRA, KLEBER T.; NEWTON, SEAN; LEY, STEVEN V.; BROCKSOM, TIMOTHY J. A practical deca-gram scale ring expansion of (R)-(-)-carvone to (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 13, n. 28, p. 7633-7642, 2015. Web of Science Citations: 7.
BROCKSOM, TIMOTHY JOHN; DESIDERA, ANDRE LUIZ; ALVES, LEANDRO DE CARVALHO; DE OLIVEIRA, KLEBER THIAGO. The New Directions of Organic Synthesis. CURRENT ORGANIC SYNTHESIS, v. 12, n. 5, p. 496-522, 2015. Web of Science Citations: 6.
MOMO, PATRICIA B.; BELLETE, BARBARA S.; BROCKSOM, TIMOTHY J.; DE SOUZA, RODRIGO O. M. A.; DE OLIVEIRA, KLEBER T. Exploiting novel process windows for the synthesis of meso-substituted porphyrins under continuous flow conditions. RSC ADVANCES, v. 5, n. 102, p. 84350-84355, 2015. Web of Science Citations: 11.
ULIANA, MARCIANA P.; SERVILHA, BRUNO M.; ALEXOPOULOS, OLGA; DE OLIVEIRA, KLEBER T.; TORMENA, CLAUDIO F.; FERREIRA, MARCO A. B.; BROCKSOM, TIMOTHY J. The Diels-Alder reactions of para-benzoquinone nitrogen-derivatives: an experimental and theoretical study. Tetrahedron, v. 70, n. 39, p. 6963-6973, SEP 30 2014. Web of Science Citations: 4.
BARBOSA, LAYLA R.; VIEIRA, YGOR W.; LACERDA, JR., VALDEMAR; DE OLIVEIRA, KLEBER T.; DOS SANTOS, REGINALDO B.; GRECO, SANDRO J.; NETO, ALVARO C.; DE CASTRO, EUSTAQUIO V. R.; BROCKSOM, TIMOTHY J. Unequivocal structural assignments of three cycloheptenoid intermediates for guaiane sesquiterpenes: an experimental and theoretical approach. Magnetic Resonance in Chemistry, v. 52, n. 6, p. 318-328, JUN 2014. Web of Science Citations: 2.
DONATONI, MARIA C.; JUNIOR, GILMAR A. B.; DE OLIVEIRA, KLEBER T.; ANDO, ROMULO A.; BROCKSOM, TIMOTHY J.; DOS SANTOS, ALCINDO A. Solvent-free Diels-Alder reactions catalyzed by FeCl3 on Aerosil((R)) silica. Tetrahedron, v. 70, n. 20, p. 3231-3238, MAY 20 2014. Web of Science Citations: 8.
DE OLIVEIRA, KLEBER T.; MOMO, PATRICIA B.; DE ASSIS, FRANCISCO F.; FERREIRA, MARCO A. B.; BROCKSOM, TIMOTHY J. Chlorins: Natural Sources, Synthetic Developments and Main Applications. CURRENT ORGANIC SYNTHESIS, v. 11, n. 1, p. 42-58, FEB 2014. Web of Science Citations: 31.
ULIANA, MARCIANA P.; PIRES, LAYLA; PRATAVIEIRA, SEBASTIAO; BROCKSOM, TIMOTHY J.; DE OLIVEIRA, KLEBER T.; BAGNATO, VANDERLEI S.; KURACHI, CRISTINA. Photobiological characteristics of chlorophyll a derivatives as microbial PDT agents. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, v. 13, n. 8, p. 1137-1145, 2014. Web of Science Citations: 19.

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