Procedure for the Rapid Synthesis of the Monomer 1,4-Bis(chloromethyl)-2-(2-ethylhexyloxy)-5-methoxybenzene

Anderson, Nichole; Bagge, Whitney; Webber, Cindy; Zarras, Peter; Davis, Matthew C.

doi:10.1080/00397910802238775

Cited by 3 publications

(4 citation statements)

References 11 publications

(5 reference statements)

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“…The required monomer for the synthesis of MEH-PPV via Gilch polymerization is readily synthesized in multigram scale via a two steps procedure. 18 In our initial attempt at solid-state Gilch polymerization promoted by ball-milling the MEH-PPV monomer and three equivalents of potassium tert-butoxide were added to a 10 mL zirconium oxide milling jar along with a 10 mm diameter zirconium oxide ball. The solid reaction mixture was subjected to vibrational ball-milling in a Retsch® mixer-mill 400 at 30 Hz for 30 minutes.…”

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confidence: 99%

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Mechanochemical Synthesis of Poly(phenylene vinylenes)

Ravnsbæk

Swager

2014

ACS Macro Lett.

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We report a simple, rapid and solvent-free methodology for solid-state polymerizations yielding poly(phenylene vinylenes) (PPV) promoted by ball-milling. This solid-state Gilch polymerization method produces PPVs in as little as five minutes of milling. Detailed investigations of the parameter space governing the solid-state polymerization, i.e. milling time, base strength, solid-state dilution, milling frequency and size of milling balls, revealed that polymerization by ball-milling is a rapid process achieving molecular number average weights of up to 40 kDa in up to 70% yield. To explore the scope, a solid-state polymerization via the dithiocarbamate precursor route is explored.

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“…MEH-PPV is among the most widely studied PPVs, owing to the excellent solubility in most organic solvents. The required monomer for the synthesis of MEH-PPV via Gilch polymerization is readily synthesized in a multigram scale via a two-step procedure …”

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confidence: 99%

Mechanochemical Synthesis of Poly(phenylene vinylenes)

Ravnsbæk

Swager

2014

ACS Macro Lett.

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“…The monomer, 1,4-Bis(chloromethyl)-2-(2-ethylhexyloxy)-5methoxybenzene was prepared according to a previously reported procedure developed by the authors [25]. The polymer, poly[2-methoxy-5-(2'-ethylhexyloxy)-1,4-phenylene vinylene], MEH-PPV was also prepared via previously reported methods [26][27][28].…”

Section: Methodsmentioning

confidence: 99%

Processing, Adhesion and Corrosion-inhibiting Properties of Poly[2-methoxy-5-(2’-ethylhexyloxy)-1,4-phenylene vinylene], (MEH-PPV) on Aerospace Aluminum Alloys

Zarras¹,

Buhrmaster²,

Stenger‐Smith³

et al. 2021

J. Coat. Sci. Technol.

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Researchers at the Naval Air Warfare Center Weapons Division (NAWCWD) and Wright-Patterson Air Force Base (WPAFB) investigated poly[2-methoxy-5-(2’-ethylhexyloxy)-1,4-phenylene vinylene], (MEH-PPV) for its potential corrosion-inhibition properties on aerospace aluminum alloy AA2024-T3. Solution processing of the polymer, as well as adhesion testing and accelerated weathering tests were performed on MEH-PPV full military aerospace coatings. Wet and dry tape adhesion testing, as well as pencil hardness, impact flexibility and pneumatic adhesion tensile test instrument (PATTI) testing were used to demonstrate the adhesion performance of MEH-PPV on aluminum substrates. The results showed that MEH-PPV had acceptable adhesion characteristics when compared to hexavalent chromium (Cr(VI)) based coatings in all of these tests. Accelerated weathering analysis was performed on MEH-PPV coatings to determine their corrosion protection and weathering resistance capabilities. These tests included neutral salt spray (NSS) exposure and xenon-arc lamp testing. The results showed that while MEH-PPV does not exhibit significant color change after 500 hours of xenon arc lamp exposure, the polymer has poor corrosion protection performance under aggressive salt environments.

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“…Synthesis of Monomer 1,4-Bis(bromomethyl)-2-(2-ethylhexyloxy)-5-methoxybenzene (1). In a first step, 1-(2-ethylhexyloxy)-4methoxybenzene was synthesized according to Anderson et al 30 A detailed description of the synthesis can be found in the Supporting Information (SI). 1 H NMR (270 MHz, CDCl 3 , TMS; ppm): δ 6.80 (s, 4H), 3.74 (d, J = 5.7 Hz, 2H), 3.73 (s, 3H), 1.66 (m, 1H), 1.21−1.52 (m, 8H), 0.82−0.90 (m, 6H).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Guided in Situ Polymerization of MEH-PPV in Mesoporous Titania Photoanodes

Minar

Docampo

Fattakhova‐Rohlfing

et al. 2015

ACS Appl. Mater. Interfaces

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Incorporation of conjugated polymers into porous metal oxide networks is a challenging task, which is being pursued via many different approaches. We have developed the guided in situ polymerization of poly(2-methoxy-5-(2'-ethylhexyloxy)-p-phenylenevinylene) (MEH-PPV) in porous titania films by means of surface functionalization. The controlled polymerization via the Gilch route was induced by an alkoxide base and by increasing the temperature. The selected and specially designed surface-functionalizing linker molecules mimic the monomer or its activated form, respectively. In this way, we drastically enhanced the amount of MEH-PPV incorporated into the porous titania phase compared to nonfunctionalized samples by a factor of 6. Additionally, photovoltaic measurements were performed. The devices show shunting or series resistance limitations, depending on the surface functionalization prior to in situ polymerization of MEH-PPV. We suggest that the reason for this behavior can be found in the orientation of the grown polymer chains with respect to the titania surface. Therefore, the geometry of the anchoring via the linker molecules is relevant for exploiting the full electronic potential of the conjugated polymer in the resulting hybrid composite. This observation will help to design future synthesis methods for new hybrid materials from conjugated polymers and n-type semiconductors to take full advantage of favorable electronic interactions between the two phases.

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Procedure for the Rapid Synthesis of the Monomer 1,4-Bis(chloromethyl)-2-(2-ethylhexyloxy)-5-methoxybenzene

Cited by 3 publications

References 11 publications

Mechanochemical Synthesis of Poly(phenylene vinylenes)

Mechanochemical Synthesis of Poly(phenylene vinylenes)

Processing, Adhesion and Corrosion-inhibiting Properties of Poly[2-methoxy-5-(2’-ethylhexyloxy)-1,4-phenylene vinylene], (MEH-PPV) on Aerospace Aluminum Alloys

Guided in Situ Polymerization of MEH-PPV in Mesoporous Titania Photoanodes

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