Preparation Of Low-Dimensional Supramolecular Functional Mat Erials Based On Perylene Bisimide And Naphthalene Bisimide

Compared with the low dimension material of one-component π conjugate organic molecules, the multiple components low dimension material is of greater value because of its components of the performance between complementary, restructuring and synergy in its functional, which is a hotspot of the current organic materials science research. Hydrogen bonding is one of the most effective means to synthesize functional material, but the study of hydrogen bonding interaction aggregate structure is still immature, so how to use the hydrogen bonding interaction to construct π-conjugated-molecular-based multicomponent low-dimensional supramolecular functional materials is still the main challenge for modern supramolecular chemistry. In this thesis, based on the design of the hydrogen bondnaphthalimide (referred to as NBI) assembly unit, the naphthalimide and perylene (referred to as PBI) were assembled as two-component low-dimensional structure functional materials, then in further study of the effect of various processing conditions on the aggregate structure, the formation mechanism of self-assembly was explored. In addition, the highly ordered low-dimensional materials of methodnaphthalimide n,n-dialkyl series molecules were successfully synthetized by means of phase transfer and the influence of the alkyl chain length on the structure of the aggregates was explored.Three kinds of new melamine compounds:NBI-D, NBI-P, NBI-MP were synthetized and their chemical structures were validated by’HNMR and FT-IR. By the study of NBI-D·PBI and PBI self-assembly process, it is found that the ultraviolet absorption spectrum of NBI-D·PBI in different solvents conditions shows that the polarity of different environment plays an important role in the formation of the lower dimensional structure with different materials, and the structure of the ordered aggregate can only be formed in the methylene chloride. The solid ultraviolet absorption of NBI-D·PBI components for mole ratio0.5:1indicated that as NBI-D components increase, the pure PBI spectral shows an increasing blue shift. Through the study of different concentrations assembly, it is found that the higher the concentration is, the easier it is to form bar structure. SEM showed the NBI-D·PBI prevalent is over70μm long,1μm wide, and with a very smooth surface, at the same time the wave interference OPM determine theπ-π direction of the bar structure. Through the OPM image and UV-Vis it is found that the hydrogen bonding interaction makes the accumulation of mode of PBI molecules change from t J-type to face-face Ⅱ-type arrangement, and gathered degree increase with time step by step. By using similar self-assembly methods, the morphology of aggregate structure of two kind of different chemical structure the NBI-P·PBI and NBI-MP·PBI were investigated, the prevalent length of NBI-P·PBI and NBI-MP·PBI is80-100μm, the diameter1μm, which is larger than the size of NBI-D·PBI, all above show the H aggregation, and the one dimensional structure aggregate all represent anisotropy. By further investigation, the π-π stacking direction of PBI aggregates is perpendicular to the direction of the long axis of the one-dimensional aggregate, while the direction of hydrogen bonding interactions between two components is parallel to the direction of the long axisBy adopting "phase transfer" preparation method, several low dimension materials based on N,N-two alkyl naphthalene imide are synthetized. The research results indicate that the higher volume ratio of "bad" solvent (methanol) against "good" solvent (chloroform) is, the more effective it is to shape a large one-dimension aggregate structure. In addition, comparison of the influence of different length of alkyl chain to aggregate the structure, the one dimensional of NBI-6aggregate reaches1cm, and the NBI-12formed branches of fibrous, a phenomenon which not currently seen any related reports in the literature. Finally, using the phase transfer method to investigate the gathered state structure NBI-D and NBI-P two self-assembly unit, it is found that NBI-D formed thorn ball structure, the global average diameter in roughly5-7μm; but NBI-P formed short fiber.