Photophysical and Electrochemical Properties of Highly pi-Conjugated Bipolar Carbazole-1,3,4-Oxadiazole-based D-pi-A Type of Efficient Deep Blue Fluorescent Dye
JOURNAL OF FLUORESCENCE(2021)
Abstract
In this contribution, we have designed and synthesized a novel carbazole-1,3,4-oxadiazole based bipolar fluorophore (E)-2-(4-(4-(9H-carbazol-9-yl)styryl)phenyl)-5-(4-(tertbutyl) phenyl)-1,3,4-oxadiazole (CBZ-OXA-IV). Wittig reaction is utilised for the synthesis of the designed bipolar target compound CBZ-OXA-IV. H-1 NMR, C-13 NMR, FT-IR and ESI-MS results confirmed the designed chemical structure of the fluorophore CBZ-OXA-IV. The photophysical properties have been investigated in detail using UV-Vis absorption, photoluminescence spectroscopy. Also, the photoluminescence studies on solid state samples (as thin films) were carried out. The CBZ-OXA- IV dye emits intense deep blue fluorescence with observed absorption and emission maxima occurring are at 353 nm and 470 nm, respectively. Fluorophore CBZ-OXA-IV has shown high Stokes shift of 7052 cm(-1). The experimentally measured optical band gap (E-g(opt)) value is found to be 3.01 eV and the fluorescence quantum yields (Phi(f)) is 0.40. The intramolecular charge transfer property of CBZ-OXA-IV dye was examined by using photophysical properties such as absorption, emission in different solvents of different varying polarities. In addition, Density Functional Theory computations are studied in detail including the MEP surface plots and natural bond orbital analysis. The electrochemical properties have been investigated in detail by using cyclic voltammetry measurements. Thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC) measurement results display a high thermal stability with decomposition temperature (T-d5%) 387 degrees C and a large glass transition temperature (Tg) of 98 degrees C. The obtained results demonstrated that the novel bipolar fluorophore CBZ-OXA-IV could play an important role in organic optoelectronics and possibly can be utilized as bipolar transport materials for electroluminescence applications in optoelectronic devices/OLEDs.
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Key words
Photophysical properties, Bipolar fluorophore, Carbazole, 1,3,4-Oxadiazole, Electrochemical properties, DFT Computations
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