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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Synthesis, spectroscopic/electrochemical characterization and DNA interaction study of novel ferrocenyl-substituted porphyrins

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Author(s):
Auras, Bruna L. [1] ; Meller, Sheila De Lucca [1] ; Da Silva, Marcos Paulo [1] ; Neves, Ademir [1] ; Cocca, Leandro H. Z. [2] ; De Boni, Leonardo [2] ; da Silveira, Carolina Hahn [3] ; Iglesias, Bernardo A. [3]
Total Authors: 8
Affiliation:
[1] Univ Fed Santa Catarina, Lab Bioinorgan & Cristalog LABINC, Dept Quim, BR-88040900 Florianopolis, SC - Brazil
[2] Univ Sao Paulo, Inst Fis Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
[3] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS - Brazil
Total Affiliations: 3
Document type: Journal article
Source: Applied Organometallic Chemistry; v. 32, n. 5 MAY 2018.
Web of Science Citations: 8
Abstract

We report the synthesis and characterization of two new meso-ferrocenylporphyrins, with the ferrocenyl unit attached at the para position of a C6F4 group by a C-N bond with -NH(CH2)(2)NH- (2a) and -NH(CH2)(4)NH- (2b) spacers. Compounds 2a and 2b were characterized through elemental analyses, electrospray ionization high-resolution mass spectrometry, H-1 NMR, UV-visible and fluorescence spectroscopies, electrochemistry and spectroelectrochemistry. The free base porphyrin 2 was included for comparison purposes. The binding ability of 2 and the porphyrin derivatives 2a and 2b with calf thymus DNA was determined using U V-visible and fluorescence spectroscopies. The results suggest that the interaction of these systems most probably occurs through pi-stacking by non-classical modes involving the partial insertion of the C6F5 ring between adjacent base pairs on DNA and possible hydrogen interaction with the aliphatic -NH(CH2)(n)NH- (n = 2 or 4) groups with calf thymus DNA. Moreover, we also demonstrate that porphyrins generate singlet oxygen species and show good photostability after irradiation. (AU)

FAPESP's process: 16/20886-1 - Ultrafast nonlinear optical spectroscopy: Transient Absorption and optical Kerr Gate with polarization control
Grantee:Leonardo De Boni
Support type: Regular Research Grants