Synthesis of Tris(2,5-dialkynylthieno)cyclotriynes, Tris(4,5-dialkoxyphenyl)cyclotriynes, and Tetrakis(4,5-dialkoxyphenyl)cyclotetraynes with Long-Chain Alkyl Substituents, and the Nickel and Cobalt Complexes of Tris[4,5-(didodecyloxy)phenyl]cyclotriyne

Abstract

This report focuses on the synthesis of materials designed to be discotic mesogens based on a cyclotriyne core with alkyl side chain substituents. With the attachment of long side chains, tris(4,5-dialkoxyphenyl)cyclotriynes and tris(2,5-dialkynylthieno)cyclotriynes are structurally similar to hexasubstituted triphenylene discotic mesophases. The syntheses of four tris(2,5-dialkynylthieno)cyclotriynes, two tris(4,5-dialkoxyphenyl)cyclotriynes, and two tetrakis(4,5-dialkoxyphenyl)cyclotetraynes are described. The interaction of one of the tris(4,5-dialkoxyphenyl)cyclotriynes with Ni(0) and Co2(CO)8 to form a mononuclear Ni(0) complex and a tetranuclear cobalt cluster are reported. Evidence is also presented to explain why the systems reported herein are not liquid crystals and suggestions for correcting this are made.