1373354-64-3Relevant academic research and scientific papers
Molecular tuning in highly fluorescent dithieno[3,2-b:2′,3′-d] pyrrole-based oligomers: Effects of N-functionalization and terminal aryl unit
Evenson, Sean J.,Pappenfus, Ted M.,Delgado, M. Carmen Ruiz,Radke-Wohlers, Karla R.,Navarrete, J. T. Lopez,Rasmussen, Seth C.
experimental part, p. 6101 - 6111 (2012/08/13)
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 Pna21 with a = 10.8666(3) A, b = 22.8858(6) A, c = 7.4246(2) A, 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 the Owner Societies 2012.
