New Phosphonic Acid Functionalized, Regioregular Polythiophenes

Stokes, Kristoffer K.; Heuzé, Karine; McCullough, Richard D.

doi:10.1021/ma034639+

Cited by 54 publications

(34 citation statements)

References 12 publications

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“…140,141 Acid-base interactions can also 142,143 be used to influence the conformation of the polymeric backbone in polythiophene derivatives 33-35, resulting in spectral changes. [144][145][146] Schwartz et al extended this concept to PPV 36 substituted with dialkylamino chains ( Figure 15). Protonation of just a few percent of the amino side groups leads to coiled polymers that in turn result in a blue-shifted absorption.…”

Section: Ionochromismmentioning

confidence: 99%

About Supramolecular Assemblies of π-Conjugated Systems

et al. 2005

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Section: Ionochromismmentioning

confidence: 99%

About Supramolecular Assemblies of π-Conjugated Systems

et al. 2005

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“…Therefore, we have carefully chosen a small size Br substituent tethered to the end of a hexyl chain to minimize the disturbance to the packing of the P3HT polymers. 3-bromohexylthiophene (2) was prepared from 3-bromothiophene (1) by reacting with n-BuLi and 1,6-dibromohexane according to the route reported by Stokes et al [34] 1,3-dibromo-5,5-dimethylhydantoin was then added to 2 affording photocrosslinkable monomer 3, 2-bromo-3-(6-bromohexyl)-thiophene. The P3HT-Br copolymers 5 were synthesized by the McCullough method [35] to produce highly regioregular polymers containing various proportions of the two monomers 3 and 4 ( Table 1).…”

Section: Synthesis and Photocrosslinking Behavior Of The New Materialsmentioning

confidence: 99%

Photocrosslinkable Polythiophenes for Efficient, Thermally Stable, Organic Photovoltaics

Kim

Miyamoto

et al. 2009

Adv Funct Materials

269

277

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Photocrosslinkable bromine‐functionalized poly(3‐hexylthiophene) (P3HT‐Br) copolymers designed for application in solution‐processed organic photovoltaics are prepared by copolymerization of 2‐bromo‐3‐(6‐bromohexyl) thiophene and 2‐bromo‐3‐hexylthiophene. The monomer ratio is carefully controlled to achieve a UV photocrosslinkable layer while retaining the π–π stacking feature of the conjugated polymers. The new materials are used as electron donors in both bulk heterojunction (BHJ) and bilayer type photovoltaic devices. Unlike devices prepared from either P3HT:PCBM blend or P3HT‐Br:PCBM blend without UV treatment, photocrosslinked P3HT‐Br:PCBM devices are stable even when annealed for two days at the elevated temperature of 150 °C as the nanophase separated morphology of the bulk heterojunction is stabilized as confirmed by optical microscopy and grazing incidence wide angle X‐ray scattering (GIWAXS). When applied to solution‐processed bilayer devices, the photocrosslinkable materials show high power conversion efficiencies (∼2%) and excellent thermal stability (3 days at 150 °C). Such performance, one of the highest obtained for a bilayer device fabricated by solution processing, is achieved as crosslinking does not disturb the π–π stacking of the polymer as confirmed by GIWAXS measurements. These novel photocrosslinkable materials provide ready access to efficient bilayer devices thus enabling the fundamental study of photophysical characteristics, charge generation, and transport across a well‐defined interface.

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“…The synthetic route 10,11 is illustrated in Scheme 1. The doubly polymerizable monomer, 3-(hexyl methacrylate)thiophene (3HMAT), was prepared by the esterification reaction of 3-(6-hydroxyhexyl)thiophene and methacryloyl chloride ( 1 H NMR spectra, Figure 1A).…”

Section: Resultsmentioning

confidence: 99%

Novel Cross‐Linked Conducting Polythiophene with Yellow‐Green‐Light‐Emitting Properties and Good Thermal Stability

et al. 2011

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A novel conjugated polythiophene derivative with polymethacrylate attaching to the polymer backbone via an alkyl spacer was successfully synthesized. A methacrylate-substituted thiophene monomer, 3-(hexyl methacrylate)thiophene was prepared and polymerized by free radical polymerization, followed by an electrochemical polymerization. The resulting polymer as a yellow-green-light emitter, has potential applications in photoelectronics area.

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New Phosphonic Acid Functionalized, Regioregular Polythiophenes

Cited by 54 publications

References 12 publications

About Supramolecular Assemblies of π-Conjugated Systems

About Supramolecular Assemblies of π-Conjugated Systems

Photocrosslinkable Polythiophenes for Efficient, Thermally Stable, Organic Photovoltaics

Novel Cross‐Linked Conducting Polythiophene with Yellow‐Green‐Light‐Emitting Properties and Good Thermal Stability

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