1,2,3-Triazoles as conjugative π-linkers in push-pull chromophores: Importance of substituent positioning on intramolecular charge-transfer

Peter D. Jarowski, Yi Lin Wu, W. Bernd Schweizer, François Diederich*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    74 Scopus citations

    Abstract

    (Chemical Equation Presented) Isomeric charge-transfer chromophores using 1,2,3-triazol-diyl as linker have been studied experimentally and computationally. The instability of the polarized reactants precluded the use of the Huisgen reaction and alternative synthetic methodologies were employed. Charge-transfer absorptions between an N,N-dimethylanilino and a dicyanovinyl group are modest to strong, with maxima from λmax = 400 to 453 nm depending on substituent positioning. TD-B3LYP/6-31G(d) calculations are within 0.6 eV of experiment and assign these bands as HOMO-LUMO transitions.

    Original languageEnglish (US)
    Pages (from-to)3347-3350
    Number of pages4
    JournalOrganic Letters
    Volume10
    Issue number15
    DOIs
    StatePublished - Dec 1 2008

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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