Development of benzoxazine macrocycles for supramolecules/molecular necklace via click chemistry

Abstract

Molecular necklace is the development of supramolecular structure based on connected mocrocycles. The preparation of molecular necklace was reported in terms of molecular interlocking, molecular assembly, etc. In the past, our group succeeded in preparing a series of benzoxazine macrocycles by esterification and etherification as simple and effective reaction. In this work, a novel type of benzoxazine macrocycle based molecular necklace was prepared by Click chemistry. The propargylamine was used for preparing of benzoxazine macrocycle containing alkyne and 1,4-dibromobutane was modified with sodium azide to obtain 1,4-dizidobutane. In the final step, click chemistry was applied to link benzoxazine macrocycle containing alkyne and 1,4-diazidobutane by triazole linkage. The FTIR spectrum shows a decreasing of azide peak implying that the azide group is developed to be triazole linkage. Moreover, the ESI mass spectrum shows m/z = 2358 referring to connecting of benzoxazine macrocycle via triazole linkag