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Synthesis 2007(21): 3323-3328  
DOI: 10.1055/s-2007-990807
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Rigid Oligofluorene Stars

Shezhad Jeevaa, Stephen C. Moratti*b
a Liquid Crystal Group, Department of Chemistry, University of York, York, Yorkshire, YO10 5DD, UK
b Department of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
e-Mail: smoratti@chemistry.otago.ac.nz;
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Publication History

Received 18 July 2007
Publication Date:
21 September 2007 (online)

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Abstract

In this paper we present the synthesis of a tetrahedral oligofluorene-functionalized adamantane, via an iterative synthetic approach, using Suzuki coupling methodology. Tetraphenyladamantane with two fluorene units on each arm were successfully synthesized. These tetrahedral oligofluorene adamantane cores exhibited good optical and thermal properties. One problem in this synthesis of these materials was that the homocoupling of the core became more prevalent as the molecular size increased. This is possibly a common defect in many controlled synthesis of large poly­arenes.

Keywords

Pd-coupling - ipso-substitution - conjugation - organometallic reagents - silylation