One Pot Synthesis of 1,10-Phenanthroline-based Shape-Persistent Flouroscent Macrocycle Using Sonogashira Coupling

Abstract

A rigid shape-persistent fluorescent macrocycle PhenMac was synthesized using Sonogashira coupling reaction and TIPS-decoupling in a single pot. 2,9-dichloro-1,10-phenanthroline was reacted with TIPS-protected diyne 2 in the presence of Pd(PPh3)(2)Cl-2, CuI and TBAF at 100 degrees C. PhenMac was obtained as yellow fluorescent compound; characterized by NMR, ESI, MALDI-TOF, CHN, IR and UV-visible spectroscopy. In chloroform, PhenMac showed lambda(ex-max) at 331 nm while lambda(em-max) was observed at 407 nm. Under UV light, PhenMac showed more fluorescence in CHCl3, ethanol, and DMF while the fluorescence was quenched in triethylamine. PhenMac will be used in various applications of [poly]catenanes, supramolecular chemistry and nanotechnology.