A Modular Synthetic Approach to Conjugated Pentacene Di-, Tri-, and Tetramers†
Dan Lehnherr
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada), Fax: (+1) 780-492-8231
Search for more papers by this authorAdrian H. Murray
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada), Fax: (+1) 780-492-8231
Search for more papers by this authorRobert McDonald Dr.
X-ray Crystallography Laboratory, Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorRik R. Tykwinski Prof. Dr.
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada), Fax: (+1) 780-492-8231
Present address: Institut für Organische Chemie, Friedrich-Alexander-Universität, Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
Search for more papers by this authorDan Lehnherr
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada), Fax: (+1) 780-492-8231
Search for more papers by this authorAdrian H. Murray
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada), Fax: (+1) 780-492-8231
Search for more papers by this authorRobert McDonald Dr.
X-ray Crystallography Laboratory, Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada)
Search for more papers by this authorRik R. Tykwinski Prof. Dr.
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 (Canada), Fax: (+1) 780-492-8231
Present address: Institut für Organische Chemie, Friedrich-Alexander-Universität, Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
Search for more papers by this authorThis work was generously supported by the University of Alberta, the Natural Sciences and Engineering Research Council of Canada (NSERC) through the Discovery grant program, and the Canadian Foundation for Innovation (CFI). D.L. thanks NSERC (PGS-D), the Alberta Ingenuity Fund (AIF) , the Alberta Heritage Fund, the Killam Trusts, and the University of Alberta for scholarship support. A.H.M. thanks NSERC (PGS-D) and AIF for scholarship support.
Graphical Abstract
Achtung, Bandlücke! Di-, tri- und tetramere Pentacene können aus einem vielfältig einsetzbaren Baustein durch Hay-Homokupplungen und auch durch Cadiot-Chodkiewicz-Kreuzkupplungen synthetisiert werden. Durch diese modulare Herangehensweise können Löslichkeit, Stabilität und HOMO-LUMO-Bandlücke der Verbindungen in Abhängigkeit von ihrer Länge bewertet werden. Im iBu3Si-substituierten Pentacen-Dimer treten weit reichende dreidimensionale π-Überlappungen auf (siehe Bild; n=2).
Supporting Information
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