Synthesis of Amphiphilic Naphthalenediimides and Investigation of Their Bioimaging Potential in Large Unilamellar Vesicles

Abstract

New fluorescent probes for bioimaging outlook are constantly required to in depth elucidate relevant biochemical processes and macrodomains. Among them the targeted imaging of cellular membranes is of high importance due to their complex biochemical function. In this work, a small library of amphiphilic core substituted 1,4,5,8-naphthalenediimides (cNDIs) has been synthesized and investigated. This approach aims to evaluate how fluorophores with the same molecular structure and hydrophilic/hydrophobic balance but bearing different small structural moieties, needed to tune their optical features, can stain the lipid bilayer membrane in large unilamellar vesicles (LUVs) as cell membrane models. The photophysical properties and the partition kinetic into different LUVs have been analysed with respect to the probe structure and the specific photophysical traits related to cNDIs core substitution spanning the whole visible spectrum. The obtained results and preliminary cell imaging analyses represent versatile key data to support the design of new amphiphilic fluorescent sensors for bioimaging.