0000000000550045

AUTHOR

Raúl García

showing 3 related works from this author

The Role of Planarity versus Nonplanarity in the Electronic Communication of TCAQ-Based Push–Pull Chromophores

2018

Donor-acceptor-substituted alkynes, endowed with 11,11,12,12-tetracyano-9,10-anthraquinodimethane (TCAQ) and N,N-dimethylaniline (DMA) units, have been further functionalized by a [2+2] cycloaddition with tetracyanoethylene (TCNE) followed by a subsequent retro-electrocyclization to form distorted nonplanar structures with bridging 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) units. Comprehensive spectroscopic, electrochemical, and computational studies have been carried out to compare the electronic communication in planar (alkyne bridges) and nonplanar (TCBD bridges) TCAQ-based push-pull chromophores. Cyclic voltammetry and UV/Vis absorption measurements confirm the electronic communication be…

chemistry.chemical_classificationMaterials science010405 organic chemistryAlkyneGeneral ChemistryTetracyanoethyleneChromophore010402 general chemistry01 natural sciencesPlanarity testingCycloaddition3. Good health0104 chemical scienceschemistry.chemical_compoundCrystallographychemistryElectronic communicationDensity functional theoryCyclic voltammetry
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A Straightforward Electroactive π-Extended Tetrathiafulvalene (exTTF) Building Block

2012

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.

ConjugationOlefinationOrganic ChemistryPhosphonium saltPi interactionSettore CHIM/06 - Chimica OrganicaPhotochemistryFused-ring systemCombinatorial chemistryMaterialchemistry.chemical_compoundchemistryBromideWittig reactionMoietyPi interactionPhysical and Theoretical ChemistryCyclic voltammetryDonor-acceptor systemTetrathiafulvaleneDerivative (chemistry)European Journal of Organic Chemistry
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Tuning the Electronic Properties of Nonplanar exTTF-Based Push–Pull Chromophores by Aryl Substitution

2012

International audience; A new family ofπ-extended tetrathiafulvalene (exTTF) donor−acceptorchromophores has been synthesized by [2 + 2] cycloaddition of TCNE with exTTF-substituted alkynes and subsequent cycloreversion. X-ray data and theoretical calculations,performed at the B3LYP/6-31G**level, show that the new chromophores exhibit highlydistorted nonplanar molecular structures with largely twisted 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) units. The electronic and optical properties, investigated by UV/visspectroscopy and electrochemical measurements, are significantly modified when theTCBD acceptor unit is substituted with a donor phenyl group, which increases the twistingof the TCBD unit…

010405 organic chemistryBand gap[CHIM.ORGA]Chemical Sciences/Organic chemistryArylOrganic ChemistryChromophore010402 general chemistryPhotochemistry01 natural sciencesAcceptorCycloaddition0104 chemical scienceschemistry.chemical_compoundchemistry[ CHIM.ORGA ] Chemical Sciences/Organic chemistryPhenyl groupSpectroscopyTetrathiafulvaleneComputingMilieux_MISCELLANEOUS
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