Synthesis And Controled Self-Assembly Of Pyridine Appended Hbc Derivatives

Self-assembled nano-materials from functional n-conjugated organic molecules have attracted increasing attention due to their potential applications in organic and supramolecular electronics. Polycyclic aromatic hydrocarbons (PAHs) could self-assemble into one-dimensional columnar structures via strong π-π stacking interactions, which show a one-dimensional conductivety as an excellent transport material. HBC is a class of polycyclic aromatic compounds. Their physicochemical properties could be optimized by substitution. And novel molecules with new optical, electric, catalytic functions could be prepared by further molecular self-assembly. In the present work, pyridine moieties were introduced into HBC. It is expected to control their self-assembly behavior by adding the metal since the long electrons pair of pyridine are easy to coordinate with metalThe thesis is divided into three parts.Part I:synthesis of pyridine appended HBC derivative. Two kinds of HBC derivatives containing pyridine unit were designed and synthesized from iodobenzene and1-bromo-4-iodobenzene as starting material via a series of classical reactions, which including. Sonogashira coupling reaction, Suzuki coupling reaction, Wolff-Kishner reduction reaction, Scholl-type oxidative cyclization.The synthesized HBC derivatives were characterized by MALDI-TOF mass spectrometry.Part Ⅱ:Physicochemical properties and self-assembly of the compound1and2. The physicochemical properties of1and2were characterized by UV-vis, fluorescence spectroscopy, differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA) measurements. And the self-assembling behaviors of1and2were discussed in different solvents. TGA result indicated that both target compounds exhibiting high thermostability their decomposition temperature over380℃. The image of Scanning electron microscopy (SEM) showed rod-like self-assembled nanostructures of compound1in toluene solution.Part III:The coordination of compound1and2with silver salts. no obvious controlled self-assembly by coordination was implied by UV-vis, fluorescence spectrometry and SEM. which might because that the interaction between nitrogen and silver coordination is too weak to adjust the π-π stacking of HBCs.