New indole trimers as precursors for molecular electronic materials

We have prepared two new C 3-symmetric, substituted-triazatruxene molecules using a facile one-pot trimerisation of 5-carboxyindole and 6-bromoindole in acetic acid using Br 2, giving 2a and 3a, respectively. These were subsequently modified by the addition of six alkyl chains to the N- and carboxyl...

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Bibliographic Details
Published in:Tetrahedron letters 2012-02, Vol.53 (6), p.657-660
Main Authors: Valentine, Robert A., Whyte, Alexander, Awaga, Kunio, Robertson, Neil
Format: Article
Language:English
Subjects:
Acetic acid
DFT
Electrochemistry
FET
Fluorescence
Mathematical analysis
Molecular electronics
Precursors
Synthesis (chemistry)
Tetrahedrons
Transistor
Triazatruxene
Trimers
Voltammetry
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Summary:We have prepared two new C 3-symmetric, substituted-triazatruxene molecules using a facile one-pot trimerisation of 5-carboxyindole and 6-bromoindole in acetic acid using Br 2, 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.11.124