Site-selective synthesis and characterization of BODIPY-acetylene copolymers and their transistor properties

To study the effect of site-selective copolymerization of borondipyrromethene (BODIPY) with acetylene on the structural and optoelectronic properties, three copolymers P1–P3 were synthesized by the Sonogashira cross-coupling of BODIPY units with diacetylene and bromine capping through all the possible linkages: α-α (P1), α-β (P2), and β-β (P3). The optoelectronic properties of the polymers were investigated systematically to understand the effect of site-selective polymerization. The HOMO levels of the polymers were significantly tuned from P1 to P3 with negligible change in the LUMO levels. Broadening of absorption spectra from P3 to P1 was observed because of increase in the extent of conjugation. Additionally, the charge transport properties of these polymers in organic thin-film transistors (OTFTs) revealed that P1 and P3 exhibited only p-type mobility, whereas P2 exhibited electron mobility. Notably, the further investigations of the surface morphology of polymer films by atomic force microscopy (AFM) unveiled that comb like nanostructural arrangements in P3 was beneficial for the charge-carrier mobility over the circular arrangements in P1 and P2. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016