Synthesis & Characterization of Tripyrrine (furan & selenophene) and Conjugated Furan Macrocycles

Abstract

Chapter 1 of this thesis deals with the synthesis of tripyrrine molecule, a subclass of modified porphyrin which was taken into consideration as a noble precursor by Dr. Martin Broering in Institut für Anorganische Chemie, Universität Würzburg to illustrate its importance [1]. The Thiophene tripyrrine molecule has already been synthesized and characterized and the same procedure/ technique were used to produce the tripyrrine molecules with different subunits such as Furan and Selenophene. The diols were synthesized by lithiating the subunits and these diols were further reacted with pyrrole to give the respective tripyrrine molecules as the product. The mass spectra were done either by MALDI-TOF or ESI-TOF spectrometric techniques for identification of the product and the proton NMRs were recorded for confirming the structure of respective molecules.The tripyrrines have Amine (NH) groups which act as good hydrogen-bond donors hence making it a good molecular candidate for co-crystals with hydrogen-bond accepting molecules. Chapter 2 of this thesis describe the products of reaction between furan and pentafluoro-benzaldehyde to give 18or the 36conjugated macrocycles. The idea was to synthesize a derivative of modified isophlorin (furan) having benzene and furan subunits in which the difuran and phenyl-diol derivative would be reacted in presence of pentafluoro-benzaldehyde and be oxidized with ferric chloride to obtain the desired product, but the isolation was unsuccessful.The mass spectra were recorded through MALDI-TOF spectrometer and the 1HNMR & 1H-1H COSY confirmed the product. Though the final products were not overwhelming, the results encourage further experimentation.