Pseudorotaxanes, and Rotaxanes into the Chemistry Curriculum for Undergraduate Students, A Gateway to Modern Molecular Design

Abstract

Design and synthesis of a 24-membered macrocyclic wheel (MC) based [2]rotaxane (ROT) with multiple functional groups are reported. Threading followed by capping strategy was used to form a mechanically interlocked structure. Initially, metal ion template [2]pseudorotaxane was formed via ternary complexations. Then, stoppering via click chemistry results [2]rotaxane. The interlocking nature was established by ESI-MS spectrometry and various 1D, 2D NMR studies. This concept also offers a valuable pedagogical framework for teaching and learning modern chemical design strategies and, the interpretation of various spectroscopic, and spectrometric data, extensive use of chem-draw software for undergraduate students. This article explores the design, synthesis and characterization of pseudorotaxane and rotaxane, importance of interlocked systems in the pedagogy at undergraduate level with the aim to deep understanding of modular synthesis and orthogonal reactivity.