Synthesis Of Some N-type Organic π-conjugated Molecules And The Positive Response To Fluoride Ion

Over the past decades, design and synthesis of novel organic π-conjugated compoundshave received more attention because of their potential application in many aspects such asorganic electroluminescence displays, organic photovoltaic cells, organic field effecttransistors, and biosensors. In comparison, the organic semiconductor materials present manyadvantages, such as easy obtainable, easily tuning the physical property, portable devices,biodegrade and friendly environment. At present, the preparation and exploitation of n-typematerials lagged behind the p-type counterpart. To envisage these problems, herein, a series ofn-type organic semiconductors were synthesized and characterized. In addition, their physicalproperties were also studied in detail. The thesis is divided into three parts:1. Two novel ladder-type conjugated molecules (10and11) were synthesized andcharacterized. Compound10shows the absorption and emission bands at410nm,443nm and472nm, respectively, whereas11exhibits red-shift absorption and emission spectra comparedto10due to its longer conjugated length. TGA analysis displayed that they have high thermalstability.2. Two novel organic semiconductors containing imidazoles21and22were synthesized andcharacterized through1H NMR,13C NMR and MALDI-TOF spectroscopy. The introductionof twisted topology structure in22might be beneficial for decreasing the π-π stackinginteraction in solid state. Compound21and22present the absorption and emission peaks at351nm and353nm and display the emission bands at441nm,458nm with the excitationwavelength at341nm.3. A novel BF2-complex derivative23was prepared through one-pot reaction of indigo andBF3·Et2O in dry methylene chloride. Single crystal analysis shows that23is a planar moleculewith intermolecular distance about3.34. The positive response of23to fluoride ion overother anions was studied in detail.