Synthesis and characterization of dibenzoborepin and its analogs

ORGN 294

Anthony Caruso Jr., and John D. Tovar, 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