Synthesis of Ferrocene−Cyclodextrin, Anthracene−Cyclodextrin, and Pyrene−Cyclodextrin [2]Rotaxane Conjugates and Their Intercomponent Behavior as Observed in NMR Spectroscopy

• Main Authors: Tumaneng, John Vincent M, Matulac, Andrea Louise, Reyes, Jude M, Baldovino, Amyel Joseph, Lumba, Joseph, Yu, Gilbert U
• Format: text
• Published: Archīum Ateneo 2022
• Subjects: anthracene; CuAAC ‘click′ reaction; ferrocene; inclusion complexation; pyrene; [2]rotaxane; Chemistry; Organic Chemistry; Physical Sciences and Mathematics
• Online Access: https://archium.ateneo.edu/chemistry-faculty-pubs/189; https://doi.org/10.1002/ajoc.202200541
• Institution: Ateneo De Manila University

Ferrocene, anthracene, and pyrene-terminated alkynylated moieties were reacted with azidized beta-cyclodextrin derivatives to form supramolecular structures under various conditions. While initial experiments concerning mono-azidized beta-cyclodextrin proved difficult to isolate and have limited solubility, their reaction with peracetylated mono-azidized beta-cyclodextrin was more facile. Introduction and threading of the macrocycle, dibenzo-24-crown-8 (DB24C8), allowed for [2]rotaxane synthesis. These compounds were characterized by infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), and mass spectrometry (MS). Among the compounds formed, the ferrocene-capped species showed promising host-guest inclusion complexation with the cyclodextrin cavity.