Stannyl derivatives of naphthalene diimides and their use in oligomer synthesis

Lauren E Polander; Alexander S Romanov; Stephen Barlow; Do Kyung Hwang; Bernard Kippelen; Tatiana V Timofeeva; Seth R Marder

doi:10.1021/ol203432x

Stannyl derivatives of naphthalene diimides and their use in oligomer synthesis

Org Lett. 2012 Feb 3;14(3):918-21. doi: 10.1021/ol203432x. Epub 2012 Jan 24.

Authors

Lauren E Polander¹, Alexander S Romanov, Stephen Barlow, Do Kyung Hwang, Bernard Kippelen, Tatiana V Timofeeva, Seth R Marder

Affiliation

¹ School of Chemistry and Biochemistry, Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, USA.

PMID: 22272760
DOI: 10.1021/ol203432x

Abstract

2-Stannyl and 2,6-distannyl naphthalene diimides (NDIs) can be synthesized through the palladium-catalyzed reaction of the appropriate bromo derivatives with hexabutylditin. The utility of these precursors in palladium catalyzed cross-coupling reactions is demonstrated by the synthesis of bi- and ter-NDI derivatives, UV-vis, cyclic voltammetry, and n-channel organic field-effect transistor data for which are compared to those of the monomeric parent NDI.