Synthesis of a Water Soluble, Monosubstituted C₆₀ Polymeric Derivative and Its Photoconductive Properties

Abstract

Atom transfer radical polymerization (ATRP) catalyzed by N,N′,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDETA)/CuBr was performed to synthesize poly(tert-butyl acrylate) with predictable molecular weight, low polydispersities, and well-defined bromine end groups. The bromine end groups have been substituted by azides. Then C 60 end-capped poly(tert-butyl acrylate) was synthesized by the reaction of C60 with PtBA-N3 in DMF. GPC measurement showed that C60 was chemically bonded to the end chain of poly(tert-butyl acrylate); i.e., the final products (PtBA-C60) were monosubstituted. 1 H NMR, FTIR, and UV-vis measurements confirmed that the water-soluble, monosubstituted C60 derivatives of poly(acrylic acid) (PAA-C60) have been obtained by hydrolysis of PtBA-C60. The photoconductivities of PtBA-C60 and PAA-C60 were measured by photoinduced xerographic discharge technique. Experimental results showed that C60 bonded in the polymers is the headstream of the photoconductivity, and an increase of the C60 content in C60 polymeric derivatives could improve the photoconductivity dramatically. The microstructures of CGL are very important for the photoconductive properties, and perfect hole-transport channels in the CGL will improve the photoconductivity notably.

Self-Assembly of Stimuli-Responsive Water-Soluble [60]Fullerene End-Capped Ampholytic Block Copolymer

“…In addition, ATRP was also employed to synthesis the well-defined poly(tert-butyl acrylate-b-styrene)-C 60 for photoconductive applications [16]. The water-soluble C 60 -containing poly(acrylic acid) (PAA-b-C 60 ) synthesized by Yang et al formed core-shell micelles in aqueous solution, which enhanced the photoconductivity of films [17]. Recently, we synthesized C 60 -containing well-defined water-soluble C 60 containing polymer systems using ATRP.…”

Novel C60‐Anchored Two‐Armed Poly(tert‐butyl acrylate): Synthesis and Characterization

“…Our group [5] also prepared star-shaped C 60 -based polyurethanes with six well-defined polymeric arms via condensation between polyhydroxylated C 60 and isocyanated polyether prepolymers. Recently, Li et al [6] and Wang et al [7] separately prepared functional polystyrene and poly(tert-butyl acrylate) with well-defined molecular weights via atom transfer radical polymerization (ATRP), and then introduced C 60 to these polymers to create C 60 -end-bonded polymers. The former was achieved by the radical addition of bromoterminated polystyrene onto a C 60 molecule, while the latter was achieved by the cycloaddition reaction of an azide end group-functionalized poly(tert-butyl acrylate) with a C 60 molecule.…”

Stimuli‐Responsive Water‐Soluble Fullerene (C60) Polymeric Systems

“…C 60 modifi ed with these kinds of polymers combines the unique properties of C 60 with the stimuli characteristics of the polymers that may extend their end-use applications in the fi elds of biotechnology and biomedicine. In recent years, a variety of stimuliresponsive water-soluble fullerene systems have been reported such as PMAA-C 60 , [ 36 ] PDMAEMA-C 60 [ 37 , 38 ] and its betainization derivative, [ 39 ] P(MAA-bDMAEMA)-C 60 , [ 40 ] PAA-C 60 , [41][42][43] and PNIPAM-C 60 systems. [44][45][46][47] Over the last two decades, various C 60 -containing polymers, including hydrophobic and hydrophilic polymers have been prepared and their structures are shown schematically in Figure 1 .…”