Synthesis and characterization of dibenzoborepin and its analogs

ORGN 294

Anthony Caruso Jr., acaruso6@jhu.edu and John D. Tovar, tovar@jhu.edu. Department of Chemistry, Johns Hopkins University, 3400 N. Charles Street, Baltimore, MD 21218
Boron-containing materials have emerged as reliable building blocks for extended π-conjugated scaffolds due to their unique optical and structural properties that result from the vacant pz-orbital of the boron. We present herein analogues of three-coordinate boron-containing ring system that consists of a seven membered, 6π-electron borepin core. Air and moisture stability is obtained by installation of different R1 substituents, while conjugation can be extended through further functionalization at the R2 positions. Preliminary UV-vis data of the dibenzoborepin system shows a blue-shifted absorption spectrum upon addition of a fluoride source. Prospects for further synthetic manipulation and incorporation into new functional materials will be addressed.

 

Heterocycles and Aromatics
1:00 PM-5:20 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- 206, Oral

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009