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Self-assembly via intermolecular hydrogen-bonding between o-/m-/p-NH2 and BF2 groups on dipyrromethenes

TitleSelf-assembly via intermolecular hydrogen-bonding between o-/m-/p-NH2 and BF2 groups on dipyrromethenes
Publication TypeJournal Article
Year of Publication2008
AuthorsShin, JY, Patrick, BO, Dolphin, D
JournalTetrahedron Letters
Volume49
Pagination5515-5518
Date PublishedSep
Type of ArticleArticle
ISBN Number0040-4039
KeywordsANALOG, boron-dipyrromethene, CHEMISTRY, EFFICIENT, HYDROGEN-BOND, LIGANDS, MOLECULES, self-assembly, SOLID-STATE
Abstract

Boron difluoride dipyrromethenes bearing configurationally different amine groups on a meso-phenyl ring were prepared and crystallized. The ortho- and para-amino groups allow the phenyl group to inductively release greater electron density into the dipyrromethenes resulting in relatively strong intermolecular hydrogen-bonding with the terminal BF2 groups, whereas the meta-analog formed weaker hydrogen-bonds. The intensities of the H-1 NMR peaks in concentrated solutions all increased with F-decoupling. (C) 2008 Elsevier Ltd. All rights reserved.

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