6533b82efe1ef96bd12928a4

RESEARCH PRODUCT

A Straightforward Electroactive π-Extended Tetrathiafulvalene (exTTF) Building Block

Andreas GouloumisM. Rosario TorresNazario MartínNazario MartínFrancesco GiacaloneRaúl GarcíaAgustín Molina-ontoria

subject

ConjugationOlefinationOrganic ChemistryPhosphonium saltPi interactionSettore CHIM/06 - Chimica OrganicaPhotochemistryFused-ring systemCombinatorial chemistryMaterialchemistry.chemical_compoundchemistryBromideWittig reactionMoietyPi interactionPhysical and Theoretical ChemistryCyclic voltammetryDonor-acceptor systemTetrathiafulvaleneDerivative (chemistry)

description

The synthesis and X-ray structure of a new and readily available exTTF derivative (6) bearing a methyltriphenylphosphonium bromide moiety as a new building block for the construction of electroactive molecules is reported. The phosphonium salt 6, which was prepared in one step from 2-hydroxymethyl-exTTF as a stable yellow solid in 84 % yield, efficiently undergoes Wittig olefination reactions with a variety of aldehydes to predominantly form the E isomer. Electronic spectra and cyclic voltammetry of the novel compounds reveal the electronic communication between the electroactive units.

https://doi.org/10.1002/ejoc.201200115