Polymer and Hybrid Electron Accepting Materials Based on a Semiconducting Perfluorophenylquinoline

Abstract

Single wall carbon nanotubes were purchased from Carbon Nanotechnologies Inc., Houston, TX (HiPCo). 2-amino-5-bromo benzophenone[1] and 4-vinylphenylboronic acid was synthesized according to previous reports [2]. 1-Bromo-4-nitrobenzene 99% (Aldrich)

A General Direct Arylation of Polyfluoroarenes with Heteroaryl and Aryl Chlorides Catalyzed by Palladium Indolylphosphine Complexes

“…Palladium-catalyzed direct arylation of polyfluoroarenes with aryl chlorides. [a,b] [a] Reactionc onditions: Aryl chlorides (0.5 mmol), polyfluorobenzenes (1.0 mmol), Pd(OAc) 2…”

“…In conclusion, we reported the first general palladium-catalyzed direct arylation of polyfluorobenzenes with heteroaryl chlorides, especially substituted 2pyridyl chlorides, using ac ombination of Pd(OAc) 2 and indolylphosphine ligand L1 as catalysts ystem. Particularly noteworthy is that the reaction conditions were mild and ac atalystl oading down to 1mol %P d could be achieved.…”

“…Particularly,2 -substitutedn itrogen-containing compounds constitute high relevance in pharmaceutical chemistry and materials ciences. [1] Examples are polymer and hybrid electron-accepting materials based on semiconducting perfluorophenylquinoline (P5FQ), [2] the sensitization of TiO 2 nanoparticles, electrodes with perfluoroaryl motif in organic semioconducting dyes for photochemical applications (Ph5FQ-TiO 2 ), [3] and betaine dyes for determination of solvent polarity (eicosanfluoro( F 20 )-substituted betaine dye) ( Figure 1). [4] Transition metal-catalyzed cross-coupling constitutes au seful methodf or connecting two aromatic building blocks together.H owever,i ntegrating an electron-deficient aromatic fragment into the target molecule is difficult.…”

“…Surprisingly,o nly XPhos (L6)l ed to ab etter yield among the ligands examined, and poor substrate conversions and prod-uct yields were observed when L5 and L7-L12 were used. Therefore, the catalyst system comprising Pd(OAc) 2 and L1 was employed to test the scope of this reaction.…”

Solution-phase molecular recognition of an azafullerene-quinoline dyad by a face-to-face porphyrin-dimer tweezer

“…Moreover, the presence of the halogen atoms enabled their straightforward transformation to azides, allowing the direct incorporation on the sp 2 skeleton of carbon nanostructures via cycloaddition reactions. [35][36][37] More specic, (tetrauoro)azidophenyl-quinolines have been employed for the functionalization of carbon nanotubes, 35,36 C 60 (ref. 36 and 37) and phenyl-C 61 -butyric acid methyl ester (PCBM).…”