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Non-linear optical, electrochemical and spectroelectrochemical properties of amphiphilic inner salt porphyrinic systems

Abstract : Three zwitterionic meso-substituted A(3)B- and AB(2)C-porphyrins containing one sulfonato alkylpyridinium substituent and three or two alkoxy-substituted phenyl groups were synthesized in good yield and fully characterized as to their physicochemical properties by a variety of techniques. This new series of inner salt donor-acceptor meso-substituted porphyrin derivatives were prepared for possible application as amphiphilic probes for membrane insertion in the area of combined second-harmonic and two-photon fluorescence cellular microscopy. To this end, the linear and nonlinear optical properties of the compounds were characterized, together with their electrochemical and spectroelectrochemical properties in non-aqueous media. The neutral design of such molecules enabled us to determine their second order non-linear properties, both by Electric Field Induced Second Harmonic Generation and Hyper-Rayleigh Scattering. Two-photon absorption cross sections of these dyes were also measured by the two-photon induced fluorescence method. The zwitterionic nature of the inner salt results in very specific solvent-dependent redox-properties, which could be rationalized in terms of solvent-dependent ion-pairing. The overall data electrochemical and photophysical data indicates that these new porphyrinic systems should be good probes for membrane potential sensing.
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https://hal-univ-bourgogne.archives-ouvertes.fr/hal-01436568
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Soumis le : lundi 16 janvier 2017 - 15:22:00
Dernière modification le : jeudi 4 août 2022 - 17:08:41

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Claude P. Gros, Clément Michelin, Griet Depotter, Nicolas Desbois, Koen Clays, et al.. Non-linear optical, electrochemical and spectroelectrochemical properties of amphiphilic inner salt porphyrinic systems. Journal of Porphyrins and Phthalocyanines, 2016, 20 (08n11), pp.1002 - 1015. ⟨10.1142/S1088424616500425⟩. ⟨hal-01436568⟩

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