ABSTRACT
In this work, the synthesis of BODIPY-phenyl-triazole labelled coumarins (BPhTCs) using a two-step approach is described. The influence of the BODIPY appending on the photophysical, electrochemical and thermal properties of the phenyl-triazole-coumarin precursors (PhTCs) was investigated. Band gap energies were measured by absorption spectroscopy (2.20 ± 0.02 eV in the solid and 2.35 ± 0.01 eV in solution) and cyclic voltammetry (2.10 ± 0.05 eV). The results are supported by DFT calculations confirming the presence of lowest LUMO levels that facilitate the electron injection and stabilize the electron transport. Their charge-transport parameters were measured in Organic Field-Effect Transistor (OFET) devices. BPhTCs showed an ambipolar transistor behavior with good n-type charge mobilities (10-2 cm2V-1s-1) allowing these derivatives to be employed as promising semiconducting crystalline and fluorescent materials with good thermal and air stability up to 250 °C.
ABSTRACT
3-(4-Formylphenyl)-triazole-coumarin hybrid chromophores (FPhTCs) were synthesized in good yields, using a click chemistry protocol, and were also structurally characterized. Their photophysical, electrochemical and thermal properties were measured demonstrating that FPhTCs are luminescent in the blue-violet region of the electromagnetic spectrum, both in solution and the solid state. They showed an electrochemical band-gap values of 2.79 ± 0.08 eV, resistivity values between 104 and 105 Ω cm and are thermally stable up to 225 °C, properties that promise FPhTCs as good candidates for optoelectronic or imaging applications. Their solution and solid state photoluminescent properties are discussed and supported by theoretical calculations.
