Synthesis And Properties Of Aza-Fused Conjugated Molecules

?-Conjugated molecules are promising candidates for a variety of potential applications, such as optoelectronics and supramolecular nanomaterials. Aimed at creating novel functionalized ?-conjugated systems, in this thesis, we have developed a new method to synthesize a series of phenanthroline like aza-fused molecules and their corresponding conjugated polymers. The structures and physical properties of these 1,10-phenanthroline-analogous aza-fused molecules and their conjugated polymers were characterized and discussed in terms of optical properties, molecular energy levels and stimuli-responsiveness.1. Bischler-Napieralski cyclization was used as the key step to synthesize a series of phenanthroline like aza-fused molecules. All the compounds obtained were characterized by 1H NMR,13C NMR and MALDI-TOF mass spectroscopy. Their molecular structures and packing modes were determined by X-ray analysis of single crystals. The optical and electrochemical properties of the target molecules were investigated by UV-vis absorption spectroscopy, fluorescence spectroscopy and cyclic voltammetry, illustrating that they are promising functional materials for the application of electronic devices.2. Dibromination of the fused rings of the above obtained aza-fused molecules successfully afforded the critical intermediates, serving as starting materials for conjugated polymers. High molecular weight copolymers with good solubility in common organic solvents or water have been synthesized by palladium (0)-catalyzed Suzuki-Miyaura-Schliiter polycondensation of the novel aza-fused molecules and fluorene-2,7-diboronic esters. Such a novel repeating unit with the analogue structure to 1,10-phenanthroline endows the copolymers sensitive to acid and metal ions, in which the water solubilized polymer obtained herein was selectively response to Fe3+. Photophysical property studies illustrated that this kind of copolymer is a promising chemosensor material.