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New intrinsic fluoroionophores with dual fluorescence: DMABN-Crown4 and DMABN-Crown5 by J.-F. Létard; S. Delmond; R. Lapouyade; D. Braun; W. Rettig; M. Kreissler is a Chemistry article available to read on EtoBox.

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## Abstract Two new intrinsic fluoroionophores, with the electronic structure of 4‐(dimethylamino)‐ benzonitrile (DMABN): 4‐(1‐aza‐4,7,10‐trioxaclyclododecyl)benzonitrile (DMABN‐Crown4) and 4‐(1‐aza‐4,7,10,13‐tetraoxacyclopentadecyl) benzonitrile (DMABN‐Crown5) were synthesized and their absorption, fluorescence spectra and quantum yields of fluorescence measured and discussed. Comparison of X‐ray data and calculations from the density functional theory (DFT) shows that from DMABN to DMABN‐Crown5 the twist angle of the amino group with respect to the phenyl plane increases while the pyramidalization of the nitrogen is not significantly affected. The activation energies (E~a~ 8.9 kJ · mol^−1^, E~d~ 23.7 kJ · mol^−1^) and the enthalpy (ΔH‐14.8 kJ · mol^−1^) involved between the __LE__ and __TICT__ states of DMABN‐Crown5 were obtained in toluene and compared with those previously published for DMABN. The greater relief of strain (larger ΔH) which accompanies the formation of the __TICT__ state in the crown derivatives, accounts for the higher proportion of __TICT__ emission recorded at room temperature. The fluorescence of DMABN‐Crown5 in acetonitrile, is altered significantly at 3 ·

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Author

J.-F. Létard; S. Delmond; R. Lapouyade; D. Braun; W. Rettig; M. Kreissler

Publisher

Elsevier Science; Wiley (John Wiley & Sons); Royal Netherlands Chemical Society; Wiley (ISSN 0165-0513)

Published

2010

Language

EN

ISBN

9781995114118

Field

Chemistry (Physical Sciences)