13C and 1H NMR spectral studies of N‐alkylmethylquinolinium salts

Jaroszewska, Jolanta; Wawer, Iwona; Oszczapowicz, Janusz

doi:10.1002/mrc.1270220510

Cited by 15 publications

(8 citation statements)

References 10 publications

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“…To the best of our knowledge, for some of those most commonly used for the synthesis of cyanines, namely the N -ethyl, -pentyl, -hexyl and -decyl substituted ones, only the 1 H-NMR spectral data for the N -ethyl quaternary salts [4,5] and the 13 C-NMR spectral data for the N -ethylquinolinium salts [5] are available.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines

et al. 2002

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The synthesis and spectroscopic characterisation of some representative N-alkyl-substituted quaternary ammonium salts derived from benzothiazole, benzoxazole, benzo-selenazole, indole and quinoline are described. These heterocyclic salts, bearing an activated methyl group in the 2-position in relation to the nitrogen atom and N-methyl, -pentyl, -hexyl and -decyl chains, are typical precursors of cyanine dyes.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines

et al. 2002

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“…The same holds for the bisisoquinolinium salts 5-8 (see Table 2). Although 1 H and 13 C NMR spectra of 1-ethylquinolinium iodide (in DMSO-d 6 ) have been reported previously, 15 two of the proposed 13 C shifts were found to be interchanged. The values of C-5 and C-8, which were reported as being 118.59 and 130.30 ppm, respectively, are actually swapped, as can be deduced from the unequivocal assignment of compounds 1-4.…”

Section: Resultsmentioning

confidence: 73%

¹H and ¹³C chemical shifts for bis(benzopyridinium) dibromides with semirigid aromatic linkers

Campos¹,

Díaz²,

Núñez³

et al. 2002

Magnetic Reson in Chemistry

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The 1 H and 13 C NMR resonances for four bisquinolinium and four bisisoquinolinium dibromides were completely and unequivocally assigned, using the concerted application of one-and two-dimensional NMR techniques including nuclear Overhauser effect difference, DEPT, COSY, HETCOR and long-range 13 C -1 H correlation spectroscopy. Atomic charges of the heterocyclic moieties of model cations such as 1-methylquinolinium and 2-methylisoquinolinium are shown to be linearly related to the 13 C chemical shifts of the cationic heads of the title compounds.

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“…After cooling to RT the precipitate was filtered off and recrystallized from ethanol in a refrigerator at −10 • C. The solid product was filtered off, dried, soluted in less water and recrystallized by a solution of ammonium hexafluorophosphate in ethanol to form the N-alkyl-quinolinium hexafluorophosphates [40]. N-sulfoalkyl-quinolinium betaines (class B) and N-sulfoalkyl-quinaldinium betaines (class C) [21]:…”

Section: N-alkyl-quinolinium Cations (Class A) and Methyl-substitutedmentioning

confidence: 99%

Intramolecular Photoinduced Electron Transfer in Zwitterionic Quinolinium Dyes – Experimental and Theoretical Studies

Engel¹,

Kaeb²,

Lanig³

2002

Zeitschrift Für Physikalische Chemie

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Fluorescence / Intramolecular Electron Transfer / Marcus Theory / Betaine / Semiempirical CalculationsQuinolinium cations and quinolinium betaines were investigated in the representative solvents water and acetonitrile at room temperature using stationary and time-resolved fluorescence spectroscopy (Single-Photon-Counting-method).Experimental results reveal that sulfoalkyl-and carboxyalkyl-quinolinium compounds display a strikingly different behavior in the two solvents. Furthermore, the fluorescence lifetime depends on the length of the spacer for the sulfoalkyl compounds in acetonitrile and the carboxyalkyl compounds in water, respectively. This suggests an intramolecular interaction of the anionic headgroups with the quinolinium system in the excited state. To support this idea, different positions at the chromophore are substituted by a methylgroup in order to perturb the proposed interaction.With the intention to understand the dynamics of the postulated photoinduced electron transfer from the anionic group onto the excited quinolinium chromophore, semiempirical quantum chemical calculations were performed on the species using the PM3 hamiltonian including solvent effects by a self consistent reaction field (SCRF).We show that the Marcus theory of electron transfer may serve as a theoretical basis for a natural interpretation of the dynamic fluorescence quenching behavior.

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¹³C and ¹H NMR spectral studies of N‐alkylmethylquinolinium salts

Cited by 15 publications

References 10 publications

Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines

Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines

¹H and ¹³C chemical shifts for bis(benzopyridinium) dibromides with semirigid aromatic linkers

Intramolecular Photoinduced Electron Transfer in Zwitterionic Quinolinium Dyes – Experimental and Theoretical Studies

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13C and 1H NMR spectral studies of N‐alkylmethylquinolinium salts

Cited by 15 publications

References 10 publications

Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines

Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical Precursors of Cyanines

1H and 13C chemical shifts for bis(benzopyridinium) dibromides with semirigid aromatic linkers

Intramolecular Photoinduced Electron Transfer in Zwitterionic Quinolinium Dyes – Experimental and Theoretical Studies

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¹³C and ¹H NMR spectral studies of N‐alkylmethylquinolinium salts

¹H and ¹³C chemical shifts for bis(benzopyridinium) dibromides with semirigid aromatic linkers