Synthesis and Characterizations of Regioregular Poly(3‐alkylthiophene) with Alter1483ting Dodecyl/1H,1H,2H,2H‐Perfluorooctyl Side Chains

Abstract

A regioregular poly[4'-dodecyl-3-(1H,1H,2H,2H-perfluorooctyl)-2,2'-bithiophene] (P3DDFT) with alternating alkyl and semifluoroalkyl side chains were synthesized. Short ethylene spacer between perfluorohexyl part and thiophene did not largely affect the absorption and emission properties of the polythiophene backbone in comparison with poly(3-dodecylthiophene) (P3DDT). P3DDFT showed a larger onset of the oxidation potential (+0.17 V) observed by cyclic voltamogram due to the electron withdrawing effect of the fluoroalkyl part. Thermal analysis and X-ray diffraction patterns indicated that P3DDFT in the solid state forms a semicrystalline lamellar structure that is similar to that of P3DDT. Ultraviolet photoemission spectroscopy was also used to investigate their electron structure in the films. Comparison of hole mobilities in the films suggested that P3DDFT could have a less ordered packing structure compared to P3DDT both in the bulk and at the dielectric interface.

Optical Anisotropy and Strong H‐Aggregation of Poly(3‐Alkylthiophene) in a Surface Monolayer

“…Regioregular P3BT‐F 17 , P3BT, and P3DDFT were synthesized following previous reports. The number‐average molecular weights ( M n ) of P3BT‐F 17 , P3BT, and P3DDFT measured by gel permeation chromatography (GPC) with eluent of CHCl 3 were 6000, 5500, and 8400, with a polydispersity index (PDI) of 1.08, 1.11, and 1.27, respectively.…”

Organic Planar Heterojunctions: From Models for Interfaces in Bulk Heterojunctions to High‐Performance Solar Cells

“…In addition to the intrinsic dipoles from the symmetric molecules at the surface, the aligned permanent dipoles of asymmetric molecules on the surface can induce a large shift in the vacuum levels. This has been achieved by using SSMs of fluoroalkylated molecules, such as F‐PCBM and P3DDFT (see Figure ), because the fluoroalkyl chains have strong permanent dipole moments. Depending on the density of the fluoroalkyl chains, the shift of the vacuum level at the film surface can be controlled.…”

Effects of a side chain sequence on surface segregation of regioregular poly(3-alkylthiophene) and interfacial modification of bilayer organic photovoltaic devices

“…However, alt-P3DDFT showed large peaks, which were attributed to a lamellar crystalline structure. 16 These results indicate that stat-P3DDFT has a low crystallinity in the solid state, owing to the random sequences of the two side chains.…”

“…Regioregular alt-P3DDT and the monomers used in this work were synthesized as previously reported. 16 2.1 Synthesis of stat-P3DDFT 2,5-Dibromo-3-(1H,1H,2H,2H-peruorooctyl)thiophene (323.4 mg, 0.55 mmol), 2,5-dibromo-3-dodecylthiophene (184.6 mg, 0.45 mmol), and anhydrous THF (10 mL) were placed in a 50 mL two-necked round-bottom ask under N 2 and cooled in an icewater bath. A hexane solution of iPrMgCl (0.45 mL, 2.0 mol L À1 , 0.9 mmol) was injected quickly with a syringe.…”