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Synfacts 2006(12): 1226-1226  
DOI: 10.1055/s-2006-955579
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Fluorescent Dialkynylboradiazaindacenes

Contributor(s): Timothy M. Swager, Julian M. W. Chan
C. Goze, G. Ulrich, R. Ziessel*
Ecole de Chimie, Polymères, Matériaux de Strasbourg, France
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Publication History

Publication Date:
22 November 2006 (online)

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Significance

A series of monomeric and dimeric dialkynylboradiazaindacene fluorophores has been prepared. The synthesis begins with the simple and easily accessible borondipyrromethene 1, which is further elaborated using well-established nucleophilic displacement, Sonogashira, and deprotection protocols. Very strong fluorescence and high quantum yields (92-98%) were measured for certain derivatives. Large virtual Stoke’s shifts and redox activity were also found.