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Synthesis 2010(20): 3569-3575  
DOI: 10.1055/s-0030-1258209
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Spiro-Annelated Zn-Phthalocyanine: A Novel Building Block for Molecular Architecture?

Herwig J. Bertholda, Joachim Thiema, Andrea Zalianib, Theo Schotten*c
a University of Hamburg, Department of Chemistry, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
b ZBH Zentrum für Bioinformatik, Bundesstr. 43, 20146 Hamburg, Germany
c CAN GmbH, Grindelallee 117, 20146 Hamburg, Germany
Fax: +49(40)428385797; e-Mail: schotten@can-hamburg.de;
Further Information

Publication History

Received 14 May 2010
Publication Date:
13 August 2010 (online)

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Abstract

The de novo synthesis of an aromatic system via [2+2+2] alkyne cyclotrimerization provided access to a fluorenyl spiro-annelated­ phthalic anhydride derivative. Its exceptional rigidity - originating from the orthogonally attached fluorenyl moiety - was confirmed by single-crystal X-ray analysis. The anhydride was used successfully as a precursor for the synthesis of a novel class of orthogonal spiro-annelated Zn-phthalocyanine, which has the potential to be used as a core for molecular architecture.

Key words

alkynes - rhodium - Wilkinson’s catalyst - cyclotrimerization - spiro compounds - phthalocyanines

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