New indole trimers as precursors for molecular electronic materials

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. (C) 2011 Elsevier Ltd. All rights reserved.