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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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