Origin of the methylene bonds in poly[2‐methoxy‐5‐(2′‐ethyl‐hexyloxy)‐1,4‐phenylenevinylene] prepared according to Gilch's method: novel applications

Abstract

Impurities containing methylene bridges between 2‐((2′‐ethylhexyl)oxy)‐5‐methoxy‐benzene molecules are inevitably formed during the synthesis of 1,4‐bis(chloromethyl)‐2‐((2′‐ethylhexyl)oxy)‐5‐methoxy‐benzene, the monomer used in the preparation of poly[2‐methoxy‐5‐(2′‐ethyl‐hexyloxy)‐1,4‐phenylenevinylene] (MEH‐PPV), but they can be removed by double recrystallization of the monomer prior to polymerization. When impurities containing methylene bridges participate in a Gilch polymerization, the methylene bonds formed in the main chains are prone to break at 200 °C, that is, at least 150 °C below the major degradation temperature of defect‐free MEH‐PPV. Interestingly, the thermal treatment used to break the methylene bonds present reduces the chain aggregation of MEH‐PPV during film formation and induces its blends with poly(2,3‐diphenyl‐5‐octyl‐p‐phenylene‐vinylene) (DPO‐PPV) to form a morphology similar to that of block copolymers. Both significantly enhance the luminescence properties. Copyright © 2006 Society of Chemical Industry

Solvent-induced photoemissions of high-energy chromophores of conjugated Polymer MEH-PPV: Role of conformational disorder

“…8,11 The concentration of the defect is an important parameter dictating the individual chain conformation and the efficiency of intrachain energy transfer. 9,14 It is possible that our results could stem from this molecular parameter.…”

“…However, the synthetic procedure usually generates some saturated bonds (or chemical defects) in the polymer backbone. [8][9][10][11] In addition, the conjugated backbone can fold or twist introducing physical defects when chain length exceeds the persistence length. [12][13][14][15][16][17][18][19] The existence of the chemical and physical defects is an important factor that dictates the photophysics of conjugated polymers.…”

Paintable Hybrids with Thermally Stable Dual Emission Composed of Tetraphenylethene-Integrated POSS and MEH-PPV for Heat-Resistant White-Light Luminophores

“…The luminescent π-conjugated polymer MEH-PPV was synthesized according to the literature. 76 We prepared two types of MEH-PPV with different molecular weights (M n = 64,000 and M w / M n = 4.8, and M n = 114,000 and M w /M n = 3.7) determined by sizeexclusion chromatography with polystyrene standards with chloroform as an eluent. Both polymers had enough molecular weights to show good film formability and saturated optical properties.…”

“…TPE-Pr was also prepared by the same condensation reaction of propylamine and 1 quantitatively. The luminescent π-conjugated polymer MEH-PPV was synthesized according to the literature . We prepared two types of MEH-PPV with different molecular weights ( M n = 64,000 and M w / M n = 4.8, and M n = 114,000 and M w / M n = 3.7) determined by size-exclusion chromatography with polystyrene standards with chloroform as an eluent.…”

Synthesis of a Fluorescent Conjugated Polymer in the Undergraduate Organic Teaching Laboratory

“…15 This procedure used Gilch polymerization conditions (mechanism discussed in the Supporting Information), 16 and required moderate precautions to limit the reaction's exposure to air and moisture. Once the polymer was synthesized, it was utilized for two applications: (a) synthesis of fluorescent organic nanoparticles; 17 and (b) fabrication of fluorescent thin films.…”