Synthesis and photophysics of a terphenylene-ethynylene macrocycle

ORGN 786

Thomas S. Hughes, Thomas.S.Hughes@uvm.edu, Andrew L. Korich, Andrew.Korich@uvm.edu, and Ian A. McBee. Department of Chemistry, University of Vermont, Cook Physical Sciences Building, 82 University Place, Burlington, VT 05405
A series of triangular, trimeric phenylene ethynylene macrocycles have been synthesized via Suzuki and Sonogashira cross-coupling reactions. These shape-persistent macrocycles have been synthesized in roughly comparable yields using two different synthetic strategies. One-step, statistical macrocyclizations of difunctional monomers have been employed as have the macrocyclizations of linear trimers synthesized by the stepwise assembly of orthogonally deprotected monomers using a split-pool strategy. Unsubstituted macrocycles are sparingly soluble in halogenated organic solvents, whereas substitution with alkyl and alkoxy substituents on the phenyl rings. The unsubstituted terphenylene ethynylene macrocycle has been shown to exhibit a strong fluorescence at 387 and 406 nm. The solution aggregation of these macrocycles has been examined, both by NMR spectroscopy and UV-VIS absorption and fluorescence spectroscopy.

 

Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007