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Bis(1-pyrenylmethyl)-2-benzyl-2-methyl-malonate as a Cu2+ Ion-Selective Fluoroionophore.

ABSTRACT: A new malonate possessing two pyrene moieties was synthesized as a fluoroionophore, and its structure and fluorescence spectroscopic properties were investigated. When excited at 344 nm in acetonitrile/chloroform (9:1, v/v), the synthesized bispyrenyl malonate has the fluorescence of intramolecular excimer (?em = 467 nm) emissions and not a pyrene monomer emission (?em = 394 nm). A large absolute fluorescence quantum yield was obtained in the solid state (?PL = 0.65) rather than in solution (?PL = 0.13). X-ray crystallography analysis clarified the molecular structure and alignment of the bispyrenyl malonate in the crystal phase, elucidating its fluorescence spectroscopic properties. Such analysis also suggests there are intramolecular C-H···? interactions and intermolecular ?···? interactions between the pyrenyl rings. Interestingly, the synthesized bispyrenyl malonate exhibits excellent fluorescence sensing for the Cu2+ ion. Remarkable fluorescence intensity enhancement was only observed with the addition of the Cu2+ ion.

SUBMITTER: Moriuchi-Kawakami T

PROVIDER: S-EPMC6151551 | BioStudies | 2017-01-01T00:00:00Z

REPOSITORIES: biostudies

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Project description:The current research mainly focuses on transforming low-quality waste into value-added nanomaterials and investigating various ways of utilising them. The hydrothermal preparation of highly fluorescent N-doped carbon dots (N-CDs) was obtained from the carboxymethylcellulose (CMC) of oil palm empty fruit bunches and linear-structured polyethyleneimines (LPEI). Transmission electron microscopy (TEM) analysis showed that the obtained N-CDs had an average size of 3.4 nm. The N-CDs were monodispersed in aqueous solution and were strongly fluorescent under the irradiation of ultra-violet light. A detailed description of the morphology and shape was established using Fourier transform infrared (FTIR) spectroscopy and X-ray photoelectron spectroscopy (XPS). It was shown that LPEI were successfully tuned the fluorescence (PL) properties of CDs in both the intrinsic and surface electronic structures, and enhanced the quantum yield (QY) up to 44%. The obtained N-CDs exhibited remarkable PL stability, long lifetime and pH-dependence behaviour, with the excitation/emission maxima of 350/465.5 nm. Impressively, PL enhancement and blue-shifted emission could be seen with the dilution of the original N-CDs solution. The obtained N-CDs were further applied as fluorescent probe for the identification of Cu2+ in aqueous media. The mechanism could be attributed to the particularly high thermodynamic affinity of Cu2+ for the N-chelate groups over the surface of N-CDs and the fast metal-to-ligand binding kinetics. The linear relationship between the relative quenching rate and the concentration of Cu2+ were applied between 1-30 µM, with a detection limit of 0.93 µM. The fluorescent probe was successfully applied for the detection of Cu2+ in real water. Moreover, a solid-state film of N-CDs was prepared in the presence of poly (vinyl alcohol) (PVA) polymer and found to be stable even after 72-h of continuous irradiation to UV-lamp. In contrast to the aqueous N-CDs, the composite film showed only an excitation independent property, with enhanced PL QY of around 47%. Due to the strong and stable emission nature of N-CDs in both aqueous and solid conditions, the obtained N-CDs are ideal for reducing the overall preparation costs and applying them for various biological and environmental applications in the future.

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Bis(1-pyrenylmethyl)-2-benzyl-2-methyl-malonate as a Cu2+ Ion-Selective Fluoroionophore.

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