Preparation and properties of calix[4]arene-based epoxy resins

Abstract

Calix[4]arene macrocycles are the subject for increasing interest in the field of supramolecular chemistry and hostguest chemistry as basic skeletons for the synthesis of host compounds for ions or neutral molecules. Although quite a large number of reports exists on the molecular calix[4] arenes, those on polymeric precursors are limited. Recently, calix[4]arene-based polymers have just begun to receive attention, as these new polymers may then be processed into materials suitable for the chemical sensor devices such as ion selective electrodes and filtration/extraction membranes. There is some structural analogy between polymeric linear phenolic novolak molecules and calixarenes which could also be called ‘cyclic phenol resin’. Thus it seems promising to further enhance the sensitivity of calixarene derivatives by applying various techniques, which are generally used to reduce the required dose of commonly used novolak resin. Up to now, this method has not been applied to the non polymeric class of calixarenes. In the microelectronic process, the smallest obtainable structure size as well as the line edge roughness is strongly influenced by the size of the typical novolak based polymeric resist molecules. Therefore, the search for prospective nonpolymeric resist materials has become a high interest. In this paper, various glycidyl calix[4]arene derivatives were prepared using ECH under different conditions, and their curing behavior and thermal properties were examined using epoxy systems with 4,4'-diaminodiphenylmethane and boron trifluoride-isopropylamine as a crosslinker and a cationic catalyst, respectively.