Peroxidase/H₂O₂ catalyzed oxidative oligomerization of 1-aminopyrene

ABSTRACT

A new florescent oligo(aminopyrene) (OAP) was successfully synthesized by enzymatic approach. For this, H₂O₂ and Horse Radish peroxidase (HRP) were used as catalyst and oxidant, respectively. The structures of monomer and oxidation product were confirmed by NMR, FT-IR and UV-Vis measurements. The oxidation product was characterized by gel permeation chromatography (GPC), thermogravimetry (TG), differential scanning calorimetry (DSC), cyclic voltammetry (CV), photoluminescence (PL) and scanning electron microscopy (SEM) analyses. OAP was soluble in a wide range of organic solvents. UV-Vis spectrum of the OAP showed a dramatic red shift compared to that of the monomer. The optical and electrochemical band gaps of OAP were found to be 1.65 and 1.56 eV, respectively. OAP emitted turquoise color in THF and green color in toluene. SEM observations indicated the presence of a heterogeneous cauliflower like morphology.

KEYWORDS:

• 1-Aminopyrene
• enzymatic polymerization
• HRP
• oxidative polymerization
• photoluminescence

Funding

The authors thank the following source for financial support: The Scientific and Technological Research Council of Turkey (TUBITAK) with project Nu.: 113Z562.