We report an efficient synthesis of chiral (2S)-ethylhexanol for functionalizing and solubilizing conjugated polymers. The alpha-substituted chiral ethylhexyl side chains were obtained through a powerful and flexible asymmetric synthesis using pseudoephedrine as a chiral auxiliary. The dependence of the properties of conjugated polymers on molecular structure is investigated by circular dichroism, fluorescence, and absorption spectroscopy on two new chiral conjugated polymers, poly(3,3-bis((S)-2-ethylhexyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine) (PProDOT((2S)-ethylhexyl)(2)) and poly(3,3-bis((S)-2-methylbutyl)-3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine) (PProDOT((2S)-methylbutyl)(2)). The properties of PProDOT((2S)-ethylhexyl)(2)) differ significantly from those of its methylbutyl analog as investigated by chiral aggregation providing insight into the role of interchain interactions in these subsecond switching electrochromic polymers.
Colored ribbons: The soluble, electron‐rich conjugated title polymer (alkyl=dodecyl) with a regiosymmetric structure was synthesized by Grignard metathesis. The polymer displays strong thermochromism in solution. AFM images of spin‐coated films show the formation of nanoribbons, and 2D‐WAXS analysis reveals 2D order in the bulk material (see picture). The polymer is thus a promising candidate for device applications.
The synthesis of well-defined second-generation PS
n
PtBA2
n
dendrimer-like copolymers based
on polystyrene (PS) and poly(tert-butylacrylate) (PtBA) is described. The synthetic procedure involves a
combination of atom transfer radical polymerization (ATRP) using multifunctional initiators and chain
end modification reactions. These structures are composed of a PS core with 2, 4, 6, or 8 arms and a
corona of PtBA with 4, 8, 12, or 16 arms, respectively. Third-generation PS
n
PS2
n
PtBA4
n
dendrimer-like
copolymers were also derived by repetition of chain end modification and ATRP. Characterization was
carried out by size exclusion chromatography online with multiangle laser light scattering and by 1H
NMR spectroscopy. PS
n
PAA2
n
amphiphilic structures based on PS and poly(acrylic acid) (PAA) were
subsequently generated by hydrolysis of the tert-butylester groups. Langmuir monolayer studies of
PS
n
PtBA2
n
showed the formation of stable films. AFM images demonstrated a significant change in
morphology upon increasing surface pressures.
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