Abstract

This work describes the synthesis and characterization of a series of arenephosphonic acid salts for use as water soluble down-converters in optogenetic assays.

Two phosphonate salts based on anthracene and naphthalene were synthesized through

cleavage of phosphonate esters. A third amphiphilic salt, developed from a long-alkylchain modified naphthalene, was produced in the same manner to demonstrate micelle

formation. Two techniques were used to determine if any of the salts showed micelle

behavior: 31P NMR and fluorescence spectroscopy. Interestingly, all three compounds

exhibited micelle formation in water. UV-induced fluorescence of NapPONa and

AntPONa revealed a secondary emission profile with maximum excitation wavelengths

that lie on top of the primary emission profile. This secondary emission can be attributed

to the emission of the micellular structure based on solid-state fluorescence experiments.

Moderate x-ray induced radioluminescence was observed in the solid forms of each

compound. A solution of amphiphilic NapPONa demonstrated both concentrationdependent and micelle-dependent radioluminescence, indicating the positioning of

aromatic rings in a micelle is inducive to a radioluminescent response. Furthermore, the

emission wavelength of this compounds lies on top of the excitation wavelength of

channelrhodopsin-2, a well-studied optogenetic target.

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1 results in micelle concentration in Keywords: micelle concentration

Synthesis and Characterization of Amphiphilic Arenephosphonates as Water-Soluble Micellular Radioluminescent Probes

1 results in Keywords: micelle concentration