The Synthesis Of β-unsubstituted Bis(Dipyrromethanes) And Structural Characterization Of Meso-tetrakis (4-lkoxyphenyl) Porphyrins And Their Metallic Complexes

Multiporphyrin arrays joined by covalent bond have been intensively studied due to their potential applications in the fields of photoelectric signal transmission and storage, molecular lines and molecular antenna. But, it is difficult to synthesize, the mainly methods are one or multi-step coupling reation, and these approaches are lower yield, much steps, difficult to purify and only introduce fixed substituting groups; therefore, we provide a general and efficient protocol to synthesize a series of novel bis(dipyrromethanes) and construct various multiporphyrin arrays with one pot.In recent years, our group attempted different methods and confirmed that InCl₃-catalyzed condensation of functionalized dialdehydes and pyrrole is a good way; Morever, we hope this approach is not only mild, but also easily operate, high-yield, efficient and universal, so as to accelerate the study of multiporphyrin compounds.In this paper, we have prepared 17 aldehydes which linkered by phenyene, triphenyene, triphenylenevinylene, carbazolene, 15 bis(dipyrromethanes) and 2 dipyrromethanes (19 of them have not been reported ), and characterized by 1H NMR, ¹³C NMR, MALDI-TOF-MS and HPLC; meanwhile, the synthesis methods of bis(dipyrromethanes) were studied.Our group have studied liquid properties of porphyrin and lubricating oil additives, in order to identify the fine structure of moleculars, develop the new function of these compounds, ten single crystals of meso–tetrakis (4-alkoxyphenyl) porphyrin and metalloporphyrins were obtained; furthermore, one lubricating oil additives was determined in this article, their crystal structures were confirmed by X-ray diffraction analyses. According to the results, different metal ions and alkoxyl groups have some influence on the porphyrin mean plane, but not significant; piperidine ring exists in the form of chair conformation, the whole molecule is in a stable condition becaude of hydrogen-bonding interactions.In addition, we found that metal complexes of meso-tetrakis (4-alkoxyphenyl) metalloporphyrin compounds can be used heterogeneous catalyst, made propylene oxide into propylene carbonate, and easily separated product from crude material. It have some important significance to re-understand and research meso-tetrakis (4-alkoxyphenyl) porphyrins complexes.