Formation of a fluorous/organic biphasic supramolecular octopus assembly for enhanced porphyrin phosphorescence in air

Chi Yang; Ravi K Arvapally; Sammer M Tekarli; Gustavo A Salazar; Oussama Elbjeirami; Xiaoping Wang; Mohammad A Omary

doi:10.1002/anie.201411462

Formation of a fluorous/organic biphasic supramolecular octopus assembly for enhanced porphyrin phosphorescence in air

Angew Chem Int Ed Engl. 2015 Apr 13;54(16):4842-6. doi: 10.1002/anie.201411462. Epub 2015 Mar 3.

Authors

Chi Yang¹, Ravi K Arvapally, Sammer M Tekarli, Gustavo A Salazar, Oussama Elbjeirami, Xiaoping Wang, Mohammad A Omary

Affiliation

¹ Department of Chemistry, University of North Texas, Denton, TX 76203 (USA). chi.yang@unt.edu.

PMID: 25735258
DOI: 10.1002/anie.201411462

Abstract

The trinuclear triangle-shaped system [tris{3,5-bis(heptafluoropropyl)-1,2,4-triazolatosilver(I)}] (1) and the multi-armed square-shaped metalloporphyrin PtOEP or the free porphyrin base H2OEP serve as excellent octopus hosts (OEP=2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphine). Coupling of the fluorous/organic molecular octopi 1 and H2OEP or PtOEP by strong quadrupole-quadrupole and metal-π interactions affords the supramolecular assemblies [1⋅PtOEP] or [1⋅H2OEP] (2 a), which feature nanoscopic cavities surrounding the upper triangular and lower square cores. The fluorous/organic biphasic configuration of [1⋅PtOEP] leads to an increase in the phosphorescence of PtOEP under ambient conditions. Guest molecules can be included in the biphasic double-octopus assembly in three different site-selective modes.

Keywords: fluorine; heterocycles; luminescent materials; porphyrins; supramolecular chemistry.