Synthesis of new H-bonding porphyrins for materials design

COLL 219

Sunaina Singh, sunnaina2002@yahoo.co.in1, Charles Michael Drain, cdrain@hunter.cuny.edu2, and Xinxu Shi2. (1) Chemistry & Biochemistry, Hunter College and Graduate Center of the City University of New York, 695 Park Avenue, New York, NY 10021, (2) Department of Chemistry, Hunter College & Graduate Center of the City University of New York, 695 Park Ave, New York, NY 10021
Porphyrins have an array of optical and redox properties that can be readily fine tuned via the choice of metal ion coordinated to the center of the macrocycle and by exocyclic groups, yet are stable under variety of conditions. We have developed a variety of strategies for the development of supramolecular porphyrinic materials, and focus on H- bonding herein. We will report on several synthetic strategies to the formation of porphyrins bearing H-bonding rigidly appended to the macrocycle, i.e. 5,10,15,20-tetrakis(1-butyl-6-uracyl)porphyrinato Zn(II); 5,10,15,20- tetrakis(1-ethylmethyl ether-6-methyl-5-uracyl)porphyrinato Zn(II); and 5,10,15,20-tetrakis(6-methyl-5-uracyl)porphyrinato Zn(II). Characterization of theses compounds and the process of their self assembly reveals that a variety of different nanostructured materials can be formed by the same porphyrin by varying solvent, evaporation rate, and surface. Thus, thin films, nano-rods, nano-ropes, and other structures can be formed. The role of the intermolecular interaction in the formation of the materials will be discussed.