Proton transfer in fluorescent secondary amines: synthesis, photophysics, theoretical calculation and preparation of photoactive phosphatidylcholine-based liposomes

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
Thais KroetzFabiano Severo Rodembusch

Abstract

In this article, new fluorescent lipophilic based benzazoles were synthesized from the reaction between photoactive formyl derivatives and aliphatic amines followed by NaBH4 reduction with good yields. The photophysics of the benzazoles was investigated experimentally and theoretically. These compounds present absorption maxima in the UV region (∼339 nm) and fluorescence emission maxima in the cyan to green region with a large Stokes shift (∼175 nm) due to a proton transfer process in the excited state. Two fluorophores were successfully used as a proof of concept to produce stable photoactive liposomes prepared from phosphatidylcholine (PC) and were characterized by zeta potential, small angle X-ray scattering (SAXS), FTIR and UV-Vis experiments (turbidity). The scattering data indicate that the presence of compounds 20 and 23 reduces the overall surface charge of the PC vesicles, possibly due to the partial neutralization of phosphatidic acid and/or phosphatidylinositol phosphate by the amine groups, and they also modify the structural features of the assemblies, leading, in particular, to a reduction in the thickness of the hydrophobic inner segment (tt) of the liposomes. DFT and TD-DFT calculations were performed with the ω...Continue Reading

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Methods Mentioned

BETA
column chromatography
X-ray

Software Mentioned

ChemCraft
SASfit
FIT2D
Gaussian
Shimatzu IR solution

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