Synthesis of dihydroindolizines for potential photoinduced work function alteration

Seeking to immobilize photochromophores on metallic surfaces, we have synthesized four molecules which contain both a photoresponsive dihydroindolizine (DHI) core and a sulfur containing moiety, which allow for their assembly onto gold substrates. Sonogashira, Suzuki, or Ullmann couplings are employ...

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Bibliographic Details
Published in:Tetrahedron letters 2010-12, Vol.51 (52), p.6839-6842
Main Authors: Bartucci, Matthew A., Wierzbicki, Patrycja M., Gwengo, Chengeto, Shajan, Sunny, Hussain, Syed H., Ciszek, Jacob W.
Format: Article
Language:English
Subjects:
Alterations
Assembly
Coupling (molecular)
Couplings
Esters
Pyridines
Tetrahedrons
Work functions
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Summary:Seeking to immobilize photochromophores on metallic surfaces, we have synthesized four molecules which contain both a photoresponsive dihydroindolizine (DHI) core and a sulfur containing moiety, which allow for their assembly onto gold substrates. Sonogashira, Suzuki, or Ullmann couplings are employed to generate pyridines with pendant thioacetates (or disulfides). The pyridines are condensed with spiro[2-cyclopropene-1,9′-[9 H]fluorene]-2,3-dimethyl ester affording the targeted DHIs.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.10.097