Synthesis, spectroscopy and computational studies of some biologically important hydroxyhaloquinolines and their novel derivatives

Małecki, Jan Grzegorz; Nycz, Jacek E.; Ryrych, Ewa; Ponikiewski, Łukasz; Nowak, Maria; Kusz, Joachim; Pikies, Jerzy

doi:10.1016/j.molstruc.2010.01.054

Cited by 16 publications

(11 citation statements)

References 20 publications

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“…A projection of the structure along the a-axis is shown in Figure 5. Bond length distribution and endocyclic bond angles in these compounds are in good agreement with different quinoline derivatives salts and other N-heterocyclic compounds [7,38,[42][43][44][45][46][47].…”

Section: C-oh C-n-c C-c-c C-c-o N···osupporting

confidence: 77%

“…Distances between the mean planes of the two quinolinium ring in each dimer is 1.79, 1.20 & 1.02, and 0.26 Å for H 2 Q + ·Cl -, Me-H 2 Q + ·Cl -and Cl-H 2 Q + ·Cl -, respectively. Such step-shaped hydrogen bounded dimers have been previously reported for 5,7-dichloro-8-hydroxy-2-methylquinolin [43], 5-chloro-8-hydroxyquinolinium chloride [35] and 8-hydroxyquinolinium chloride [34]. However, the computational results obtained in the gas-phase do not show such a step-shaped dimer.…”

Section: C-oh C-n-c C-c-c C-c-o N···omentioning

confidence: 72%

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Formation of R44(8)$R_4^4(8)$ ring in chloride salts of 8-hydroxyquinolinium derivatives: synthesis, structural, and theoretical studies

Mohammadnezhad¹,

Amini²,

Langer³

et al. 2015

Zeitschrift Für Kristallographie - Crystalline Materials

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The molecular structures of chloride salts of 2-and 5-substituted derivatives of 8-hydroxyquinoline, Me-H 2 Q + ·Cl -([C 10 H 10 NO]Cl) and Cl-H 2 Q + ·Cl -([C 9 H 7 ClNO] + ·Cl -), were determined by single crystal X-ray diffraction methods; the latter is a new polymorph. In the crystal structures of these salts, several intra-and inter-molecular interactions result in a step-shaped centrosymmetric 4 4 ( 8) R ring. Unlike most quinolinium salts, there was no solvent present in these structures. Protonation of the quinoline N atom had an effect on the N···O bite distances and C-N-C angle and greater conjugation of the benzene ring with a hydroxyl group was also observed. π-π Interactions between each pair of quinolinium rings were observed in Me-H 2 Q + ·Cl -but not in Cl-H 2 Q + ·Cl -. In addition, the quantum chemical calculations were performed on the new structures as well as similar compounds for comparison. The optimized structures were compared with the experimental observations for the effect of protonation and of hydrogen bonding interactions.

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Section: C-oh C-n-c C-c-c C-c-o N···osupporting

confidence: 77%

Section: C-oh C-n-c C-c-c C-c-o N···omentioning

confidence: 72%

Formation of R44(8)$R_4^4(8)$ ring in chloride salts of 8-hydroxyquinolinium derivatives: synthesis, structural, and theoretical studies

Mohammadnezhad¹,

Amini²,

Langer³

et al. 2015

Zeitschrift Für Kristallographie - Crystalline Materials

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“…In previous studies [3], we have reported the synthesis and characterization of some hydroxyquinolines and their methyl and phosphinyl derivatives by using microanalyses (C, H, N), IR, UVVis, multinuclear NMR spectroscopic techniques, and single crystal X-ray diffraction method. X-ray crystal structure analysis showed the presence of hydrogen-bond donating and accepting sites between the pyridine and hydroxyl functional groups.…”

Section: Resultsmentioning

confidence: 99%

“…This transformation relies on in situ generation of Fischer's type carbenes which subsequently participates in a S E Ar reaction. Our recent studies [3] reported the NBO work of hydroxyquinolines. The atomic charge calculations can give a feature for the relocation of the electron density of the compounds, but the local concentration and local depletion of electron charge density allow us to determine whether the electrophile can be attracted.…”

Section: Synthetic Remarksmentioning

confidence: 99%

“…The conversion of fluoride analogue 2c to styryl derivatives should give so called ''NMR probe'' to enhance our understanding of inhibitorenzyme interaction, thus to facilitate the design of more biologically active compounds. 2c has a potentially rich chemistry due to its relating to 2-methylquinolin-8-ol (1a) and 5,7-dichloro-2-methylquinolin-8-ol, which have received significant attention to its strong antibacterial, antifungal, trichomonal and keratoplastic effect, but also because they are important synthetic intermediates in preparing a variety of biologically active compounds [3]. Our studies of biological activity of thioanalogues of hydroxyquinoline carboxylic acids are in progress.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, spectroscopy and computational studies of selected hydroxyquinoline carboxylic acids and their selected fluoro-, thio-, and dithioanalogues

Nycz

Malecki

2013

Journal of Molecular Structure

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The 8‐Hydroxyquinolinium Cation as a Lead Structure for Efficient Color‐Tunable Ionic Small Molecule Emitting Materials

Adranno

Renier

Bousrez

et al. 2023

Advanced Photonics Research

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Albeit tris(8‐hydroxyquinolinato) aluminum (Alq3) and its derivatives are prominent emitter materials for organic lighting devices, and the optical transitions occur among ligand‐centered states, the use of metal‐free 8‐hydroxyquinoline is impractical as it suffers from strong nonradiative quenching, mainly through fast proton transfer. Herein, it is shown that the problem of rapid proton exchange and vibration quenching of light emission can be overcome not only by complexation, but also by organization of the 8‐hydroxyquinolinium cations into a solid rigid network with appropriate counter‐anions (here bis(trifluoromethanesulfonyl)imide). The resulting structure is stiffened by secondary bonding interactions such as π‐stacking and hydrogen bonds, which efficiently block rapid proton transfer quenching and reduce vibrational deactivation. Additionally, the optical properties are tuned through methyl substitution from deep blue (455 nm) to blue‐green (488 nm). Time‐dependent density functional theory (TDFT) calculations reveal the emission to occur from which an unexpectedly long‐lived S1 level, unusual for organic fluorophores. All compounds show comparable, even superior photoluminescence compared to Alq3 and related materials, both as solids and thin films with quantum yields (QYs) up to 40–50%. In addition, all compounds show appreciable thermal stability with decomposition temperatures above 310 °C.

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Synthesis, spectroscopy and computational studies of some biologically important hydroxyhaloquinolines and their novel derivatives

Cited by 16 publications

References 20 publications

Formation of R44(8)$R_4^4(8)$ ring in chloride salts of 8-hydroxyquinolinium derivatives: synthesis, structural, and theoretical studies

Formation of R44(8)$R_4^4(8)$ ring in chloride salts of 8-hydroxyquinolinium derivatives: synthesis, structural, and theoretical studies

Synthesis, spectroscopy and computational studies of selected hydroxyquinoline carboxylic acids and their selected fluoro-, thio-, and dithioanalogues

The 8‐Hydroxyquinolinium Cation as a Lead Structure for Efficient Color‐Tunable Ionic Small Molecule Emitting Materials

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