141029-75-6Relevant articles and documents
A simple and efficient route to N-functionalized dithieno[3,2-b:2′,3′-d]pyrroles: Fused-ring building blocks for new conjugated polymeric systems
Ogawa, Katsu,Rasmussen, Seth C.
, p. 2921 - 2928 (2003)
A general synthetic route has been developed for the simple and efficient preparation of N-functionalized dithieno[3,2-b: 2′,3′-d]pyrroles. These synthetic methods utilize N-functionalized N-(3′-thienyl)-3-aminothiophenes produced from the Pd-catalyzed am
Searching for Models Exhibiting High Circularly Polarized Luminescence: Electroactive Inherently Chiral Oligothiophenes
Benincori, Tiziana,Appoloni, Giulio,Mussini, Patricia Romana,Arnaboldi, Serena,Cirilli, Roberto,Quartapelle Procopio, Elsa,Panigati, Monica,Abbate, Sergio,Mazzeo, Giuseppe,Longhi, Giovanna
, p. 11082 - 11093 (2018)
Two new inherently chiral oligothiophenes characterized by the atropisomeric 3,3′-bithianaphtene scaffold functionalized with fused ring bithiophene derivatives, namely 4H-cyclopenta[2,1-b3:4b′]dithiophene (CPDT) and dithieno[3,3-b:2′,3′-d]pyrrole (DTP), were synthesized. The racemates were fully characterized and resolved into antipodes by enantioselective HPLC. The enantiomers were analyzed through different chiroptical techniques: electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) were employed to attribute the absolute configuration (AC). Comparison of experimental and calculated VCD spectra confirmed the DFT calculated conformational characteristics. The compound functionalized with two CPDT units was oxidized with FeCl3, and ECD and CPL of the resulting material were measured. Circularly polarized luminescence (CPL) was measured to verify if inherently chiral oligothiophenes could be promising systems for chiral photonics applications.
Highly disordered polymer field effect transistors: N-alkyl dithieno[3,2-b:2′,3′-d]pyrrole-based copolymers with surprisingly high charge carrier mobilities
Liu, Junying,Zhang, Rui,Sauve, Genevieve,Kowalewski, Tomasz,McCullough, Richard D.
scheme or table, p. 13167 - 13176 (2009/03/12)
A series of novel electroactive and photoactive conjugated copolymers based on N-alkyl dithieno[3,2-b:2′,3′-d]pyrroles (DTP) and thiophene (TH) units (DTP-co-THs) were synthesized using a Stille coupling reaction and exhibited molecular weights of 1.6 × 104 to 5.0 × 10 4 g/mol. The incorporation of soluble substituted thiophenes and planar DTP units resulted in low band gap, highly conductive polymers. DTP-co-THs exhibited excellent solubility in common organic solvents and formed high-quality films. Optical characterizationrevealed that the band gaps of DTP-co-THs were between 1.74 and 2.00 eV , lower than regioregular poly(3-alkylthiophenes). Electrochemical characterization showed that the HOMO energy levels of DTP-co-THs are between-4.68 and -4.96 eV. When doped, DTP-co-THs exhibited high conductivitie s up to 230 S/cm with excellent stability. The different thiophene substituent patterns' effect on the polymers' optical and electronic properties was then examined by density functional theory computations. The microstructure and surface morphologies of poly(2,6-(4-dodecyl-4H-bisthieno[3,2-b:2′,3′-d]pyrrole)-random-2, 5-(3-dodecylthiophene)) (P4) and poly(2-(4,4′-didodecyl-2,2′- bithiophen-5-yl)-4-octyl-4H-bisthieno[3,2-b:2′,3′-d]pyrrole) (P6) thin films were studied by X-ray diffraction and atomic force microscopy. As-cast P4 and P6thin films exhibited poorly defined, randomly ordered lamellar structur e that improved significantly after thermal annealing. Field effect transistor devices fabricated from P4 and P6 showed typical p-channel transistor behavior. Interestingly, the mobilities of as-cast, less ordered samples were much higher than those observed after annealing. The highest values of maximum and average mobilities were observed for the polymer P6 as-cast (0.21 and 0.13 cm2 V-1 s-1, respectively). One of our goals was to test the idea that high mobility and excellent electrical and structural reproducibility could perhaps be achieved by the creation of amorphous ?-conjugated materials that could possess long arrange ? connectivity on the microscopic scale. The results of these studies strongly suggest that the presence of highly ordered microcrystalline structures in thin films of organic semiconductors is not necessary for excellent performance of organic transistors.