Fluorescence studies on 2-(het)aryl perimidine derivatives

Giani, Arianna Maria; Lamperti, Marco; Maspero, Angelo; Cimino, A.; Negri, Roberto; Giovenzana, Giovanni B.; Palmisano, Giovanni; Nardo, Luca

doi:10.1016/j.jlumin.2016.07.033

Cited by 12 publications

(10 citation statements)

References 31 publications

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“…As observed for most of the perimidines, which either do not present luminescence or have very low emission intensities with quantum yield (Φ) of order of 10 –3 ‐10 –5 , the strongly conjugated perinones of the MP type did not emit , , , . However, the perinones of less extended conjugation, such as SP or IP , showed a remarkably strong emission with Φ ca.…”

Section: Resultsmentioning

confidence: 90%

“…The so‐called β‐absorption is a complex broad band with several local maxima which is peaked at 310 nm and looks like a superposition of β‐bands from SP and MP . As mentioned above, not all perimidine structures exhibit the longest wavelength CT band, or sometimes it does not manifest as a well‐defined peak, which can lead to mistakenly acceptance of β‐band as CT absorption, as it happened in a recently published study on absorption and emission properties of several perimidine derivatives . Based on semiempirical quantum‐mechanical calculations carried out in 1967, the authors attributed the band around 340 nm as a CT band, though the perimidine compounds studied showed the weak absorption around 450 nm.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Characterization, and Spectroscopic Properties of Allylic Ruthenium(II) Complexes of a Highly Conjugated Perinone

et al. 2019

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Highly conjugated perinones were evaluated as proligands with [Ru(η 6 -arene)Cl 2 ] 2 precursors (arene = p-cymene or benzene). None of them, except itaco-perinone (IP) bearing one exocyclic methylene group, were able to form coordination compounds. Expected η 1 -coordination through the lone pair of the nitrogen or oxygen atoms of the perinone did not occur. Instead a deprotonation reaction involving the exocyclic methylene was observed and the corresponding [Ru(η 6 -arene)- [a] 3494 (η 3 -IP)Cl] complex was isolated in moderate yields. Mechanistic studies revealed that the base-promoted isomerization of itacoperinone to citraco-perinone prevented higher yields in the synthesis of the allylic complexes. Additionally, it was observed that IP can dimerize through the exocyclic methylene group, indicating high reactivity of this carbon-carbon double bond. Electronic absorption and emission properties of the perinones and organometallic compounds were studied.

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Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, and Spectroscopic Properties of Allylic Ruthenium(II) Complexes of a Highly Conjugated Perinone

et al. 2019

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“…The details on samples preparation are provided in the Materials and Methods section. The binding isotherms (i.e., graphs of fluorescence at 460 nm plotted as a function of DNA concentration) obtained starting from 1 dissolved in DMSO and DMF are shown in Figure 6 , together with the pertaining best-fitting curves according to the independent binding site model [ 58 , 59 ], i.e., using the following equation:

…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization and DNA-Binding Affinity of a New Zinc(II) Bis(5-methoxy-indol-3-yl)propane-1,3-dione Complex

et al. 2021

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The novel zinc(II) µ-oxo-bridged-dimeric complex [Zn2(µ-O)2(BMIP)2] (BMIP = 1,3-bis(5-methoxy-1-methyl-1H-indol-3-yl)propane-1,3-dione), 1, was synthetized and fully characterized. The spectral data indicate a zincoxane molecular structure, with the BMIP ligand coordinating in its neutral form via its oxygen atoms. Structural changes in 1 in dimethylsulfoxide (DMSO) were evidenced by means of spectroscopic techniques including infrared absorption and nuclear magnetic resonance, showing DMSO entrance in the coordination sphere of the metal ion. The resulting complex [Zn2(µ-O)2(BMIP)2(DMSO)], 2, readily reacts in the presence of N-methyl-imidazole (NMI), a liquid-phase nucleoside mimic, to form [Zn2(µ-O)2(BMIP)2(NMI)], 3, through DMSO displacement. The three complexes show high thermal stability, demonstrating that 1 has high affinity for hard nucleophiles. Finally, with the aim of probing the suitability of this system as model scaffold for new potential anticancer metallodrugs, the interactions of 1 with calf thymus DNA were investigated in vitro in pseudo-physiological environment through UV-Vis absorption and fluorescence emission spectroscopy, as well as time-resolved fluorescence studies. The latter analyses revealed that [Zn2(µ-O)2(BMIP)2(DMSO)] binds to DNA with high affinity upon DMSO displacement, opening new perspectives for the development of optimized drug substances.

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“…They are used as intermediates in dyes, dyeing and polymerization systems (Watanab et al, 1977) and have been recognized as new carbene ligands (Bazinet et al, 2003), attracting great interest (Bu et al, 2001;Starshikoy et al, 1973). 1-H Perimidines also exhibit important biological activities (Zhou et al, 2019), having the potential to act as anti-inflammatory agents (Zhang et al, 2017) and inhibitors of enzymes (Alam et al, 2016) and to have applications in fluorescence (Giani et al, 2016), catalysis (Behbahani et al, 2017), corrosion inhibition (He et al, 2018) and in coordination chemistry (Booysen et al, 2016;Mahapatra et al, 2015).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)phenol

et al. 2020

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The asymmetric unit of the title compound, C17H14N2O, contains two independent molecules each consisting of perimidine and phenol units. The tricyclic perimidine units contain naphthalene ring systems and non-planar C4N2 rings adopting envelope conformations with the C atoms of the NCN groups hinged by 44.11 (7) and 48.50 (6)° with respect to the best planes of the other five atoms. Intramolecular O—H...N hydrogen bonds may help to consolidate the molecular conformations. The two independent molecules are linked through an N—H...O hydrogen bond. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (52.9%) and H...C/C...H (39.5%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

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Fluorescence studies on 2-(het)aryl perimidine derivatives

Cited by 12 publications

References 31 publications

Synthesis, Characterization, and Spectroscopic Properties of Allylic Ruthenium(II) Complexes of a Highly Conjugated Perinone

Synthesis, Characterization, and Spectroscopic Properties of Allylic Ruthenium(II) Complexes of a Highly Conjugated Perinone

Synthesis, Characterization and DNA-Binding Affinity of a New Zinc(II) Bis(5-methoxy-indol-3-yl)propane-1,3-dione Complex

Crystal structure, Hirshfeld surface analysis and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)phenol

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