Currently, polyaniline (PANI) is
considered as a promising polymer
that can be used in biosensors, drug delivery systems, bioelectronics,
etc. Its biocompatibility can be strongly improved by using dopants
with biofunctionality. This study reveals the protonation/doping of
PANI by fluorinated analogs of natural amino acids, namely, α,α-difluoro-β-amino
acids (DFAAs) with alkyl and aromatic tails in
N
-methylpyrrolidone
solutions. We find that these acids can dope PANI due to both the
weakened basicity of their amino groups because of two fluorine atoms
in α,α-positions and specific intermolecular interactions
(π–π stacking, alkyl−π, F−π)
of their tails with units of PANI chains. These interactions did not
give the doped PANI salts with high conductivity but led to formation
of stable PANI-DFAA complexes, which were confirmed both by clear
changes in the UV–Vis and Fourier transform infrared spectra
of the protonated/doped PANI and by their conductivity of ∼10
–6
S/cm. Our results suggest an applicability of such
PANI complexes as carriers of DFAA for their biomedical applications.