930-96-1Relevant articles and documents
A convenient preparation of thieno[3,2-c]pyrazole 1
Airey, John,Barrague, Matthieu,Edwards, Michael L.,Ferro, Michael,Friedrich, Dirk,Gillespy, Timothy A.,Jurcak, John,Musick, Kwon,Weintraub, Philip M.
, p. 96 - 100 (2014)
A practical synthesis of multigram quantities of 1H-thi-eno[3,2-c]pyrazole is presented in which the Jacobson reaction serves as the key step. Georg Thieme Verlag Stuttgart · New York.
The Effect of Ring Expansion in Thienobenzo[ b]indacenodithiophene Polymers for Organic Field-Effect Transistors
Chen, Hu,Wadsworth, Andrew,Ma, Chun,Nanni, Alice,Zhang, Weimin,Nikolka, Mark,Luci, Alexander M. T.,Perdig?o, Luís M. A.,Thorley, Karl J.,Cendra, Camila,Larson, Bryon,Rumbles, Garry,Anthopoulos, Thomas D.,Salleo, Alberto,Costantini, Giovanni,Sirringhaus, Henning,McCulloch, Iain
supporting information, p. 18806 - 18813 (2019/11/28)
A fused donor, thienobenzo[b]indacenodithiophene (TBIDT), was designed and synthesized using a novel acid-promoted cascade ring closure strategy, and then copolymerized with a benzothiadiazole (BT) monomer. The backbone of TBIDT is an expansion of the well-known indacenodithiophene (IDT) unit and was expected to enhance the charge carrier mobility by improving backbone planarity and facilitating short contacts between polymer chains. However, the optimized field-effect transistors demonstrated an average saturation hole mobility of 0.9 cm2 V-1 s-1, lower than the performance of IDT-BT (～1.5 cm2 V-1 s-1). Mobilities extracted from time-resolved microwave conductivity measurements were consistent with the trend in hole mobilities in organic field-effect transistor devices. Scanning tunneling microscopy measurements and computational modeling illustrated that TBIDT-BT exhibits a less ordered microstructure in comparison to IDT-BT. This reveals that a regular side-chain packing density, independent of conformational isomers, is critical to avoid local free volume due to irregular packing, which can host trapping impurities. DFT calculations indicated that TBIDT-BT, despite containing a larger, planar unit, showed less stabilization of planar backbone geometries in comparison to IDT-BT. This is due to the reduced electrostatic stabilizing interactions between the peripheral thiophene of the fused core and the BT unit, resulting in a reduction of the barrier to rotation around the single bond. These insights provide a greater understanding of the general structure-property relationships required for semiconducting polymer repeat units to ensure optimal backbone planarization, as illustrated with IDT-type units, guiding the design of novel semiconducting polymers with extended fused backbones for high-performance field-effect transistors.
Convergent Synthesis of Fluorene Derivatives by a Rhodium-Catalyzed Stitching Reaction/Alkene Isomerization Sequence
Nishida, Masaki,Shintani, Ryo
supporting information, p. 7475 - 7479 (2019/05/16)
A convergent synthetic method for the synthesis of fluorene derivatives has been developed by devising a rhodium-catalyzed stitching reaction/alkene isomerization sequence. The reactions proceed smoothly under mild conditions for a variety of substrate combinations, and extended π-conjugation systems are also readily accessible by utilizing this synthetic method. Optical properties of the obtained fluorene derivatives have also been examined.
