The present work reports, for the first time, synthesis
of dye
incorporated o-phenylenediamine (OBB) with a view
to obtain a conjugated oligomer with enhanced functionality. The structure
was confirmed by IR studies, while the electronic transitions were
confirmed by UV visible studies. The dye modified oligomer showed
one order higher fluorescence intensity than the pristine Bismarck
Brown (BB) dye. Confocal imaging showed red emission which could be
utilized in near infra-red imaging. Density functional theory (DFT)
studies were carried out to predict the theoretical properties of
the oligomers. The energies of the highest occupied molecular orbital
(HOMO) and the lowest unoccupied molecular orbital orbital were computed
to explore how the HOMO energies of the reactants initiated the electronic
interactions between them. The interaction energies were correlated
to conjugation/hyper conjugation stabilization energies of the natural
bond orbitals (NBO) via the DFT method using the B3LYP functional
with the 6-311G(d) basis set on Gaussian 09 software. Drug binding
was evaluated through simulation of interaction energy, (ΔE
A–x
) with drugs such as captopril, propranolol, thiazide, and fentanyl.
The results predicted that the oligomer could be developed into a
fentanyl drug sensor.