Pyrrole Amide Benzo Crown Ether Ions On The Synthesis And Crystal Structure Of Identifying The Main Study

Supramolecular chemistry is the science studying on the intermolecular weak interactions and their assemblies which may have special structures and functions. It has developed rapidly and become one of the challenging fields. Ion-pair recognition, named as simultaneously binds both anionic and cationic guests by one host, can diminish the effect of counterion. At present, it has become a new emerging field in supramolecular chemistry.By combination of anionic binding site, pyrrolic amide, with cationic binding site, crown ether, we have successfully designed and synthesized three new compounds of 4,5-di-(1-H-pyrrole-2-carboxamides)-benzo-crown ether, which may have the potential ability for the binding ion-pair.This dissertation is made up of three parts. The origin, development and application of the ion-pair recognition have been elaborated in the first part.In the second part, the synthesis of three target compounds has been introduced in detail. The best procedure of every step has been summarized. Fifteen compounds have been synthesized in this dissertation and most of them have been characterized by ~1H NMR, MS etc. To the best of our knowledge, five compounds, 4,5-dinitrobenzo-12-crown-4(4), 4,5-diaminobenzo- 12-crown-4(5), 4,5-di-(1-H-pyrrole-2-carboxamides)-benzo-12-crown-4(8), 4,5-di-(1-H-pyrrole-2-carboxamides)-benzo-15-crown-5(11) and 4,5-di-(1-H-pyrrole-2-carboxamides)-benzo-18-crown-6(16), haven't been reported. The last three are the target ion-pair hosts.The crystal structures of the three target compounds have been studied by the X-ray diffraction in the third part. Through the different hydrogen-bonding motifs, they exhibit different topology. For example, the crystal structure of 8 is a 3-D architecture, whereas each of 11 and 16 contains 1-D motif with the different crystal packing.Due to the participation of the crown ether or methanol, the pyrrolic amide moieties of three target compounds comprise some new hydrogen-bonding motifs, which are different from the previous observation. In crystal structure of 8, the pyrrole NH group form N-H…O hydrogen bond with the oxygen atom of the crown ether. In the crystal structure of 11, the pyrrole NH group form N-H…O hydrogen bond with the oxygen atom of methanol. In the crystal structure of 16, the pyrroLe NH group form N-H…O hydrogen bond with the oxygen atoms both on the crown ether and the methanol. It may attribute to the steric factor and the oxygen atoms of crown ether or methanol are better hydrogen bond acceptor than carbonyl oxygen atoms. X-diffraction studies also indicate that the three target compounds could be applied to molecular recognition as ion-pair recognition hosts.