Controlling the molecular weight of poly(2,5‐bis[ N ‐methyl‐ N ‐hexylamino]phenylene vinylene) using nitrobenzene as an inhibitor

2021 ◽  
Author(s):  
Michael D. Garrison ◽  
Ania Sotuyo ◽  
John D. Stenger‐Smith ◽  
Lawrence C. Baldwin ◽  
Alfred J. Baca
Keyword(s):  
Molecular Weight ◽  
Phenylene Vinylene

Preparation and Properties of a Hydrolytically Stable Cyclooctyne-Containing Polymer

Synlett ◽  
2018 ◽  
Vol 29 (19) ◽  
pp. 2535-2541
Author(s):  
Alex Adronov ◽  
Kelvin Li ◽  
Stuart McNelles
Keyword(s):  
Molecular Weight ◽  
Ethylene Glycol ◽  
Monomethyl Ether ◽  
Phenylene Vinylene ◽  
Cross Linking ◽  
Poly Ethylene Glycol ◽  
Ethylene Glycol Monomethyl Ether ◽  
Glycol Monomethyl Ether ◽  
Poly Ethylene

A poly[(phenylene vinylene)-co-dibenzocyclooctyne] polymer prepared by Wittig polymerization chemistry between dibenzocyclooctyne bisaldehyde [DIBO-(CHO)2] and bis(triethyleneglycol)phenylbis(tributylphosphonium) dibromide is reported. The resulting polymer exhibits moderate molecular weight (Mn: 10.5 kDa, Mw: 21.3 kDa, Ð: 2.02) and is fluorescent. It could be readily functionalized by strain-promoted alkyne-azide cycloadditon with different azides, and fluorescence of the polymer was preserved after functionalization. Grafting azide-terminated 5 kDa poly(ethylene glycol) monomethyl ether chains drastically affected the solubility of the polymer. Cross-linking the polymer with poly(ethylene glycol) that was terminated at both ends with azide groups gave access to a fluorescent organogel that could be dried and reswollen with water to form a hydrogel.

scholarly journals Thioalkyl- and Sulfone-Substituted Poly(p-Phenylene Vinylene)s

2018 ◽  
Author(s):  
Martina Rimmele ◽  
Klaus Ableidinger ◽  
Adam V. Marsh ◽  
Nathan J. Cheetham ◽  
M. Josef Taublaender ◽  
...  
Keyword(s):  
Molecular Weight ◽  
High Molecular Weight ◽  
Low Cost ◽  
Photophysical Properties ◽  
Quantum Yields ◽  
Phenylene Vinylene ◽  
Structural Variations ◽  
Interesting Class ◽  
New Applications ◽  
Exceptional Stability

Poly(p-phenylene vinylene)s (PPVs) have been studied for decades, but research on this interesting class of conjugated polymers is far from being completed. New applications like in bioimaging keep emerging and even simple structural variations are still waiting to be explored. Surprisingly, not even dithioalkyl-substituted PPVs (S-PPVs) have been reported in the peer-reviewed literature, although the corresponding dialkoxy-substituted PPVs (O-PPVs) like MEH-PPV or MDMO-PPV are most frequently used and although thioalkyl substituents can improve the material properties significantly. We herein report the development of a highly efficient, scalable two-step synthesis of Gilch monomers for S-PPVs starting from low-cost 1,4-diiodobenzene. A low-temperature polymerization protocol has been developed for these monomers, affording high-molecular weight S-PPVs in excellent yields. The thermal, electrochemical, and photophysical properties of S-PPVs are reported to highlight the potential of these polymers. Furthermore, treatment with dimethyldioxirane is demonstrated to result in rapid conversion into sulfone-substituted PPVs (SO<sub>2</sub>-PPVs), introducing a route to high-molecular weight SO<sub>2</sub>-PPVs with exceptional stability and solid-state photoluminescence quantum yields of up to 0.46.

Synthesis, doping, and electrical conductivity of high molecular weight poly(p-phenylene vinylene)

Polymer ◽  
1987 ◽  
Vol 28 (4) ◽  
pp. 567-573 ◽  
Author(s):  
D.R. Gagnon ◽  
J.D. Capistran ◽  
F.E. Karasz ◽  
R.W. Lenz ◽  
S. Antoun
Keyword(s):  
Electrical Conductivity ◽  
Molecular Weight ◽  
High Molecular Weight ◽  
Phenylene Vinylene ◽  
High Molecular Weight Poly

scholarly journals Thioalkyl- and Sulfone-Substituted Poly(p-Phenylene Vinylene)s

2018 ◽  
Author(s):  
Martina Rimmele ◽  
Klaus Ableidinger ◽  
Adam V. Marsh ◽  
Nathan J. Cheetham ◽  
M. Josef Taublaender ◽  
...  
Keyword(s):  
Molecular Weight ◽  
High Molecular Weight ◽  
Low Cost ◽  
Photophysical Properties ◽  
Quantum Yields ◽  
Phenylene Vinylene ◽  
Structural Variations ◽  
Interesting Class ◽  
New Applications ◽  
Exceptional Stability

Poly(p-phenylene vinylene)s (PPVs) have been studied for decades, but research on this interesting class of conjugated polymers is far from being completed. New applications like in bioimaging keep emerging and even simple structural variations are still waiting to be explored. Surprisingly, not even dithioalkyl-substituted PPVs (S-PPVs) have been reported in the peer-reviewed literature, although the corresponding dialkoxy-substituted PPVs (O-PPVs) like MEH-PPV or MDMO-PPV are most frequently used and although thioalkyl substituents can improve the material properties significantly. We herein report the development of a highly efficient, scalable two-step synthesis of Gilch monomers for S-PPVs starting from low-cost 1,4-diiodobenzene. A low-temperature polymerization protocol has been developed for these monomers, affording high-molecular weight S-PPVs in excellent yields. The thermal, electrochemical, and photophysical properties of S-PPVs are reported to highlight the potential of these polymers. Furthermore, treatment with dimethyldioxirane is demonstrated to result in rapid conversion into sulfone-substituted PPVs (SO<sub>2</sub>-PPVs), introducing a route to high-molecular weight SO<sub>2</sub>-PPVs with exceptional stability and solid-state photoluminescence quantum yields of up to 0.46.

Third Order Non-Linear Optical Properties of Polyphenylene Vinylene Derivatives in the Infrared Range

2001 ◽  
Vol 665 ◽  
Author(s):  
Yuri A. Dubitsky ◽  
Antonio Zaopo ◽  
Andrea Zappettini ◽  
Giulia Facchini ◽  
Franco D Amore ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Optical Properties ◽  
Phenylene Vinylene ◽  
Infrared Range ◽  
Third Harmonic ◽  
The Third ◽  
Excitonic Absorption ◽  
Non Linear ◽  
Linear Optical Properties ◽  
Linear Optical

ABSTRACTThe non-linear optical properties of poly[1,4-phenylene-1-phenyl vinylene], poly[1,4-phenylene-1,2-di(4′-phenoxyphenyl) vinylene], poly[2,5-dioctyloxy-1,4-phenylene vinylene] and poly[2- methoxy -5- (2'-ethylhexyloxy)-1,4-phenylene vinylene] MEH-PPV with different molecular weights were studied by the Third Harmonic Generation (THG) technique. The dispersion of the χ3 coefficient was measured in the wide infra red range from 1.2 up to 2.1 μm. It was shown that the highest χ3 value, observed for the high molecular weight MEH-PPV (Mw 230.000), reaches the maximum of 8x10-11 esu at 1.77 μm. At the same time, the medium molecular weight MEH-PPV (Mw 95.000) demonstrated not significantly different χ3 value of 6x10-11 esu. The dispersion of the χ3 coefficient was compared to the absorption of the third harmonic beam and strong χ3 enhancement relative to the excitonic absorption was observed. However, a surprising shift of about 70 nm towards the longer wavelengths between the two peaks was always observed for all studied PPV derivatives. The results of THG measurements were compared to those obtained by conventional Zscan technique in the same range. It was shown that the THG χ3 values in infrared range were up to one order of magnitude lower than those of direct Z-scan measurements.

scholarly journals Self-assembled hybrid hydrogels based on an amphipathic low molecular weight peptide derivative and a water-soluble poly(para-phenylene vinylene)

RSC Advances ◽  
2017 ◽  
Vol 7 (16) ◽  
pp. 9562-9566 ◽  
Author(s):  
Jenifer Rubio-Magnieto ◽  
Marta Tena-Solsona ◽  
Beatriu Escuder ◽  
Mathieu Surin
Keyword(s):  
Molecular Weight ◽  
Self Assembly ◽  
Water Soluble ◽  
The Self ◽  
Phenylene Vinylene ◽  
Low Molecular Weight ◽  
Hybrid Hydrogel ◽  
Conjugated Polyelectrolyte ◽  
Hybrid Hydrogels ◽  
Peptide Derivative

The self-assembly of an amphipathic low molecular weight peptide and a water-soluble π-conjugated polyelectrolyte is studied in order to form hybrid hydrogel materials with synergistic properties.

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