Abstract
Ultrasound-assisted synthesis of water soluble poly(o-phenylenediamine) (POPD) and its doping with Acid Orange (AO), Fluorescein (Fluo) and Rhodamine-6G (R6G) dyes was carried out with a view to enhance the photophysical properties of POPD. XPS studies confirmed that doping of POPD occured through hydrogen bonding between NH group of POPD and C=O/SO−, S=O groups of the dyes. The presence of strong hydrogen bonding was also confirmed via UV-vis studies by the addition of urea and sodium chloride to the dye modified POPD adducts. Molar extinction coefficient of these adducts was found to bear a close relationship with the molecular structure. Fluorescence life time, (τf,) was found to be lowest (1.8 ns) for AO-POPD and highest (3.2 ns) for Fluo-POPD. The structure of AO-POPD was more strained, while that of Fluo-POPD was least strained. Intrinsic fluorescence decay constant, (k0f) showed increasing values for POPD, AO-POPD, Fluo-POPD, R6G-POPD as 0.071, 0.072, 0.153, and 0.172 (108 s−1), which could be correlated to the increasing strain-free molecular structure of the adducts. Circular dichroism spectra (CD) of BSA in presence of POPD and R6G- POPD revealed that it partially broke its helical structure, while Fluo-POPD and AO-POPD showed enhancement in the helical content. The 3-D fluorescence studies confirmed enhancement in hydrophobicity of POPD and R6G- POPD and increase in hydrophylicity of AO-POP and Fluo-POPD in the microenvironment of tryptophan residue-213 of BSA. Fluo-POPD and R6G-POPD adducts were chosen to find out the lowest detection limit (LOD) of BSA by differential pulse voltammetry (DPV) which was found to be 1.35 nM, and 1.65 nM using Fluo-POPD and R6G -POPD respectively. The binding constant of BSA with Fluo-POPD- and R6G-POPD was obtained as 3.98 × 106 Lmol−1 and 5.27 × 102 Lmol−1. These polymers could therefore, be used for the detection of BSA. Live cell imaging revealed that POPD nanoparticles were bound to the outer membrane of E. coli, while R6G-POPD, showed penetration into the cytoplasm and excellent labeling of E. coli. This facile technique could be used to design tunable biomarkers by tailoring the conjugated polymer with a desired dye molecule.
Highlights
Acid Orange (AO), Fluorescein (Fluo) and Rhodamine-6G (R6G) dyes was carried out with a view to enhance the photophysical properties of POPD
Fluorescein interacted through the C=O of xanthene ring which is in the same plane as the –NH– group of POPD, Fig. 2(b)
The binding constant values of Bovine serum albumin (BSA) were obtained as 3.98 × 106 Lmol−1 and 5.27 × 102 Lmol−1 in presence of Fluo-POPD and R6G-POPD respectively
Summary
Acid Orange (AO), Fluorescein (Fluo) and Rhodamine-6G (R6G) dyes was carried out with a view to enhance the photophysical properties of POPD. The addition of increasing amounts of POPD (10−4 M) to AO dye solution (10−5 M) (given in Supplementary Information as Fig. S4(a)), revealed that the intensity of AO monomer peak decreased substantially from 1.25 to 0.3. The addition of AO-POPD to AO dye solution showed reduction in the intensity of the AO monomer and dimer peaks of AO dye, (given in Supplementary Information as Fig. S4(d)).
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