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New indole trimers as precursors for molecular electronic materials
Authors:Robert A Valentine  Alexander Whyte  Kunio Awaga  Neil Robertson
Institution:1. School of Chemistry and EaStCHEM, University of Edinburgh, King’s Buildings, West Mains Road, Edinburgh EH9 3JJ, UK;2. Department of Chemistry and Research Center of Materials Science, Nagoya University, Chikusa-ku, Nagoya 464-8602, Japan
Abstract:We have prepared two new C3-symmetric, substituted-triazatruxene molecules using a facile one-pot trimerisation of 5-carboxyindole and 6-bromoindole in acetic acid using Br2, giving 2a and 3a, respectively. These were subsequently modified by the addition of six alkyl chains to the N- and carboxyl-positions of 2a giving 2b and three alkyl chains to the N-positions of 3a giving 3b. The new molecules were characterised using cyclic voltammetry, UV/vis and emission spectroscopy, DFT calculations and in the case of 3b, field-effect transistor measurements showing gate-modulated source-drain current. These represent a straightforward route to large polyaromatic molecules with easily-modified side groups and are suitable as building blocks for synthesis of functional molecules for materials.
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