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synthesis and structure of d3h-symmetric triptycene trimaleimide合成和结构d3h-symmetric triptycene trimaleimide.pdf

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synthesis and structure of d3h-symmetric triptycene trimaleimide合成和结构d3h-symmetric triptycene trimaleimide

Molecules 2010, 15, 226-232; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Synthesis and Structure of D3h-Symmetric Triptycene Trimaleimide Cristiano Zonta 1,2,*, Ottorino De Lucchi 2, Anthony Linden 3 and Martin Lutz 4 1 Dipartimento di Scienze Chimiche, Università di Padova, via Marzolo 1, 35131 Padova, Italy 2 Dipartimento di Chimica, Università Ca’ Foscari di Venezia, Dorsoduro 2137, I-30123 Venezia, Italy; E-Mail: delucchi@unive.it (O.D.L.) 3 Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland 4 Bijvoet Centre for Biomolecular Research, Crystal and Structural Chemistry, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands * Author to whom correspondence should be addressed; E-Mail: cristiano.zonta@unipd.it. Received: 16 December 2009; in revised form: 24 December 2009 / Accepted: 30 December 2009 / Published: 7 January 2010 Abstract: A new D3h symmetric triptycene derivative has been synthesized with the aim of obtaining molecules that are able to assemble into porous structures, and can be used in the development of new ligands. The synthesis involves a Diels-Alder reaction as the key step, followed by an oxidation and the formation of a maleimide ring. Triptycene trimaleimide furnished single crystals which have been analyzed by means of X-ray diffraction. Keywords: tripodal ligand; cycloaddition; symmetry; triptycene Introduction The advantages offered by high-symmetry molecules are widely recognize