Synthesis and self-assembly of functionalized donor-sigma-acceptor molecules

Hengfeng Li; Edwin A Homan; Andrew J Lampkins; Ion Ghiviriga; Ronald K Castellano

doi:10.1021/ol047597y

Synthesis and self-assembly of functionalized donor-sigma-acceptor molecules

Org Lett. 2005 Feb 3;7(3):443-6. doi: 10.1021/ol047597y.

Authors

Hengfeng Li¹, Edwin A Homan, Andrew J Lampkins, Ion Ghiviriga, Ronald K Castellano

Affiliation

¹ Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611-7200, USA.

PMID: 15673260
DOI: 10.1021/ol047597y

Abstract

[structure: see text] 3,5,7-Tris(arylmethyl)-1-aza-adamantanetrione donor-sigma-acceptor compounds have been synthesized in four steps. Computational and (1)H NMR analyses rationalize the solubility, gelation, and conformational properties of the C3-symmetric molecules toward employing sigma-coupled donor-acceptor interactions in molecular self-assembly.