Molecular tuning in highly fluorescent dithieno[3,2-b:2′,3′-d] pyrrole-based oligomers: Effects of N-functionalization and terminal aryl unit

Sean J. Evenson, Ted M. Pappenfus, M. Carmen Ruiz Delgado, Karla R. Radke-Wohlers, J. T.López Navarrete, Seth C. Rasmussen

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    28 Scopus citations

    Abstract

    A series of eight conjugated oligomers consisting of central dithieno[3,2-b:2′,3′-d]pyrroles (DTPs) end-capped with either thienyl or phenyl groups have been prepared from N-alkyl-, N-aryl-, and N-acyl-dithieno[3,2-b:2′,3′-d]pyrroles via Stille and Suzuki cross-coupling. The DTP-based quaterthiophene, N-phenyl-2,6-bis(2-thienyl) dithieno-[3,2-b:2′,3′-d]pyrrole was characterized via X-ray crystallography and was found to crystallize in the orthorhombic space group Pna2 1 with a = 10.8666(3) Å, b = 22.8858(6) Å, c = 7.4246(2) Å, and Z = 4. The full oligomeric series was thoroughly investigated via photophysical, electrochemical, and DFT calculations in order to correlate the cumulative effects of both aryl end-groups and N-functionalization on the resulting optical and electronic properties. Through such molecular tuning, it was found to be possible to modulate the HOMO energy by as much as 0.32 V and to generate highly fluorescent oligomers with solution fluorescence efficiencies as high as 92%. This journal is

    Original languageEnglish (US)
    Pages (from-to)6101-6111
    Number of pages11
    JournalPhysical Chemistry Chemical Physics
    Volume14
    Issue number17
    DOIs
    StatePublished - May 7 2012

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