The Syntheses And Properties Of Rigided And Conjugated Compounds Based On Triptycene And Porphyrins

Triptycene has attracted more and more attention, not only for its specific structure, but also its attractive application prospects in many aspects, for example,molecular machines, supramolecular chemistry, material chemistry and organic reactions. Three benzene rings constitute the internal free volume, so it is an ideal receptor that provide π electron. Porphyrin compounds, which have unique conjugated structure, show excellent physical and chemical properties and other functional properties. Those compounds widely exist in living organisms and the nature of porphyrins. They exhibit good light stability and they are ideal photosensitizer that widely applied as materials on organic solar cells, organic electroluminescent materials and optical storage materials. This paper is based on triptycene and porphyrin skeleton to design and synthesize the new compounds and studied their UV-vis light absorption properties of cyclic voltammetry. Our work provide a theoretical and experimental reference for the applycation of porphyrin and triptycene in the field of photovoltaic material. The research summarized as follows:(1) In order to synthesize the target molecule, we adopt the method of step by step nitration to decorate triptycene skeleton. Six amino groups are introduced in benzene ring of triptycene.(2) Pyrene has great conjugated structure and good photoelectric properties. If it condensation with porphyrin and triptycene, the target molecules will have a stronger conjugate.(3) we used 3,5-di-tert-butyl-benzaldehyde and pyrrole to synthesize porphyrin. The β position of porphyrin was modified by nitration, and an amino group was introduced in ortho.(4) The target compounds were characterized by 1H NMR, 13 C NMR, mass spectrometry. Their optical and the relationship between structure-performance were investigated by cyclic voltammetry and UV-Vis spectra.