dc.description.abstract | The three-dimensional rigid iptycene frameworks such as triptycene and pentiptycene have found versatile usages in constructing molecules of both fundamental and practical importance. While the synthesis of many parent iptycenes is well-documented, further functionalization of their phenyl rings with both high regioselectivity and precise control of stoichiometry appears to be rather difficult in view of their high molecular symmetry. Although significant progress in the synthesis of more extended iptycene quinones has been made in the past years, transformation of these quinones to functionalized iptycenes has been poorly developed. To expedite the pentiptycene as well as larger iptycene chemistry, methodologies for facile synthesis of new iptycene building blocks are highly demanded.
This thesis is aimed to develop efficient methodologies for the synthesis of new middle-ring monsubstituted or disubstituted pentiptycenes from pentiptycene quinones. We have successfully used deamination, halogenation, alkylation, cyaniding, and reduction reactions to prepare our target compounds. One of the substituents is a amino, diazo, nitro, chloro, bromo, iodo, cyano, or formyl group and the other is a hydrogen, hydroxy, alkoxy, or perfluoro-1-butane sulfonyloxy group. These functionalized pentiptycenes are potential building blocks for constructing novel pentiptycene-incorporated systems. | en_US |