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4H-Pyran-4-ylidenes: Strong Proaromatic Donors for Organic Nonlinear Optical Chromophores

Abstract :

Merocyanines where a polyenic spacer separates a 4H-pyran-4-ylidene moiety and different strong organic acceptors have been synthesized. According to NMR studies and X-ray diffraction data, these compounds have weakly alternated structures and remarkably zwitterionic ground states, with a partial aromatic character that is compared to those of other pyran derivatives. The proaromaticity of the 4H-pyran-4-ylidene donor lies behind the cyanine-like behavior and low (positive or negative) second-order optical nonlinearities of the shorter derivatives. On the other hand, lengthening the π-spacer gives rise to rapidly increasing μβ1907 values up to 17,400 × 10−48 esu.

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https://hal.univ-angers.fr/hal-03027817
Contributeur : Okina Université d'Angers <>
Soumis le : vendredi 27 novembre 2020 - 12:28:13
Dernière modification le : samedi 28 novembre 2020 - 03:27:37

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Citation

Raquel Andreu, Laura Carrasquer, Santiago Franco, Javier Garín, Jesús Orduna, et al.. 4H-Pyran-4-ylidenes: Strong Proaromatic Donors for Organic Nonlinear Optical Chromophores. Journal of Organic Chemistry, American Chemical Society, 2009, 74 (17), pp.6647 - 6657. ⟨10.1021/jo901142f⟩. ⟨hal-03027817⟩

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