New Base-Doped Polyfluorene Derivatives

Abstract

A series of new well-defined acidic poly(2,7-fluorene) derivatives have been synthesized by palladium-catalyzed Suzuki couplings. Upon deprotonation (i.e., base doping), these conjugated polymers generate stable polymeric anions counterbalanced by alkali metal cations. The resulting polymeric salts exhibit interesting conducting properties. For instance, base-doped poly[2,7-(9,9-dioctylfluorene)-alt-2,7-((4-hexylphenyl)fluorene-9-carbonyl)] exhibits an electrical conductivity of 10-2−10-3 S/cm in air, at room temperature. In all these polymeric systems, a strong polarization of the electrical conduction is observed which seems to indicate a significant ionic transport. These electrical properties confirm the good potential of these novel acidic fluorene-based π-conjugated polymers for the development of various electrical and electrochemical solid-state devices.

The effect of complexation with platinum in polyfluorene derivatives: A photo- and electro-luminescence study

“…R f ¼ 0. 35 [39,40] To a mixture of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (6) (29 mmol) and dibromo compounds,…”

“…In Scheme 1, two molecules of 2,5-dibromopyridine that were linked together through a typical aryl-aryl coupling using palladium as catalyst in a strong alkaline medium as described in Ref. [37][38][39][40][41] are brominated. No major side products were formed, and the starting material could be easily recovered from the crude product mixture by sublimation.…”

“…produce white crystals with overall yield of 97% with higher purity for this one step reaction [39]. The bromo derivative (5) was converted to the 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (6) by lithiating the compound in diethyl ether at low temperature, followed by reaction with the borolan ester derivative as described elsewhere [48].…”

3D Monodisperse Oligofluorenes with Non‐Conjugated Triphenylamine‐Based Cores: Synthesis and Optoelectronic Properties

“…All other reagents were purchased from Alfa Aesar and used without further purification. (4-Bromophenyl)(phenyl)p-tolylamine, [18] 2,7-dibromofluorenone [19] and 9,9,9Ј,9Ј-tetra-n-octyl-2,2Ј-bifluorenyl-7-boronic acid [20] were prepared according to literature procedures. (p-tolyl)amino)]phenylboronic Acid (1): nBuLi (2.5  in nhexane, 6 mL, 15 mmol) was slowly added to a solution of (4-bromophenyl)(phenyl)p-tolylamine (3.88 g, 11.5 mmol) in anhydrous tetrahydrofuran (30 mL) at -78°C under nitrogen.…”

Controlling Polymer Solubility: Polyfluorenes with Branched Semiperfluorinated Side Chains for Polymer Light‐Emitting Diodes

“…[23] The favorable optical and electronic properties of PFs originate from their p-conjugated backbones, whereas other properties such as solubility, polarity, film-forming, and aggregation behavior can be adjusted by their side chains. [24,25] However, although very useful for tuning the overall properties of the target compound, side chains also dilute the optically and electronically active moieties; thus potentially lowering the output per mass of polymer. Therefore, finding an optimal size and structure of the side chains is a perpetual goal in polymer design.…”