Preparation, X-ray structure and properties of a hexabrominated, symmetric indole trimer and its TCNQ adduct: a new route to functional molecular systems

N Robertson, S Parsons, E J MacLean, R A Coxall, A R Mount

Research output: Contribution to journalArticlepeer-review

Abstract

Reaction of indole with Br-2 led to isolation of an indole trimer 2, formed by linking the 2- and 3-positions of each indole to form a central aromatic ring, and brominated at the 5- and 6-positions of each indole. The X-ray structure of [2]. acetone . 2DMF showed pi-stacking of the planar aromatic molecules with two different overlap modes with interplanar distances of 3.287 Angstrom and 3.378 Angstrom. Cyclic voltammetry showed one reversible oxidation for 2 and phosphorescence from frozen ethanol solution was observed. The X-ray structure of the adduct [2][TCNQ](2) . 4DMSO was determined and showed a mixed stack arrangement where 2 alternates with two adjacent TCNQ molecules.

Original languageEnglish
Pages (from-to)2043-2047
Number of pages5
JournalJournal of Materials Chemistry
Volume10
Issue number9
Publication statusPublished - 2000

Keywords

  • INDOLE-5-CARBOXYLIC ACID
  • ELECTROPOLYMERIZATION
  • METALS

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