2,5‐Substituted PPV‐Derivatives with Different Polarities: The Effect of Side Chain Polarity on Solubility, Optical and Electronic Properties

Abstract

Three 2,5‐substituted polar PPV derivatives have been prepared using the sulfinyl precursor route and compared to the apolar MDMO‐PPV. All polymers were obtained in excellent yield and with improved purity as compared to other methods. The influence of the polarity of the side chains, i.e. oligo(oxyethylene) and alkyl substituents, on the optical and electronic properties were investigated. In thin films, the oligo(oxyethylene) substituents do not significantly alter the optical properties of the conjugated backbone and the field effect mobility. In contrast, other thin film electrical properties, such as relative permittivity and conductivity, are markedly affected by the polar substituents. This is also the case for their solubility and solution properties. The polar PPV‐derivatives are not only soluble in a wide range of solvents, but also exhibit aggregation phenomena.magnified image

Charge dissociation in polymer:fullerene bulk heterojunction solar cells with enhanced permittivity

“…The synthesis and characterization have been previously reported. 13 Furthermore, previous studies using impedance measurements have shown the relative permittivity of the material to be equal to 4. 14 The chemical structure of phenyl-C 61 butyric acid 2-ethylhexyl ester ͑PCB-EH͒, which is the acceptor used here, is also shown in Fig.…”

The Gilch Synthesis of Poly(p‐phenylene vinylenes): Mechanistic Knowledge in the Service of Advanced Materials

“…Examples are the Wessling, [26] sulfinyl, [27][28][29][30][31][32][33][34] sulfonyl, [35,36] xanthate, [37][38][39] dithiocarbamate, [40] Gilch, Heck, [69][70][71][72][73] Suzuki, [74,75] McMurry, [76] ring-opening metathesis, [77,78] acyclic diene metathesis, [79][80][81] Wittig, [82][83][84] Horner-Emmons, [85] Knoevenagel, [86] chemical vapor deposition, [87][88][89][90][91] and electropolymerization [92] methods. By assessing the pros and cons of all these approaches, the Gilch route stands out as one of the most powerful, versatile, and economically efficient approaches: simply by the treatment of a,a 0 -dihalogenated p-xylene derivatives 1 with potassium tert-butoxide (KO t Bu), high-molecular-weight PPVs 2 can be obtained in good to excellent yields (Scheme 1).…”

Multiresponsive Behavior of Functional Poly(p-phenylene vinylene)s in Water

“…It is well known that the optical properties of CPs are governed by the polarity of the polymer, conformational changes in the backbone, the polarity of the solvent, intramolecular dynamics, and interchain interactions [ 55 , 56 ]. A change in the conformation of the polymer chain is dictated by different variables, among which solvent and temperature are prominent.…”

“…Fluorescence intensity increased for both of the polymers as pH values increased, without shifting of emission maxima peaks ( Figure 3 c,d). A slight blue shift is observed for PDTriG with decreasing acidity, at pH 6 and below, due to aggregation of amphiphilic CPs as they become protonated [ 56 ]. It was, however, observed that the fluorescence intensity of PDTriG decreased in time at pH 13 and at pH 6 and lower.…”