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

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

Volume: 12 Issue: 7

Author(s): Said Nadeem, Muhammad R. Shah, Qamar Ali and Zahid Hussain

Affiliation:

Keywords: Shape-persistent Macrocycles, Sonogashira Coupling of Aryl chlorides, 1, 10-phenanthroline, Fluorescent Macrocycles.

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)₂Cl₂, CuI and TBAF at 100 °C. PhenMac was obtained as yellow fluorescent compound; characterized by NMR, ESI, MALDI-TOF, CHN, IR and UVvisible spectroscopy. In chloroform, PhenMac showed λ_ex-max at 331 nm while λ_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.

Cite this article as:

Nadeem Said, R. Shah Muhammad, Ali Qamar and Hussain Zahid, One Pot Synthesis of 1,10-Phenanthroline-based Shape-Persistent Flouroscent Macrocycle Using Sonogashira Coupling, Letters in Organic Chemistry 2015; 12 (7) . https://dx.doi.org/10.2174/157017861207150708113303