Synthesis and characterization of soluble poly(3,4-phenylenedioxythiophene)

Shibasaki, Kosuke; Watanabe, Mari; Kijima, Masashi

doi:10.1016/j.synthmet.2015.03.027

Cited by 9 publications

(10 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The absorption peaks of PPhDOTV and PPhDOTFV in the film state were significantly red-shifted compared with that of PPhDOT. 13 These results indicate that the 2,5-thienylenevinylene structure effectively extends the O-conjugated length of the polymer backbone. Both PPhDOTV and PPhDOTFV exhibited two absorption peaks around 638 and 701 nm.…”

Section: Synthesis and Fundamental Properties Of Pphdotv Andmentioning

confidence: 85%

“…Both PPhDOTV and PPhDOTFV exhibited extended Oconjugation along the polymer backbones, which resulted in an absorption edge at longer wavelengths, up to 747 nm (an optical E g value of 1.66 eV) compared to those of PPhDOT (1.85 eV). 13 When a fluorine substituent was introduced into the phenylene part of PhDOT, both the HOMO and LUMO energy levels of PPhDOTFV became 0.2 eV deeper than those of PPhDOTV. BHJ OPVs with PPhDOTV exhibited a PCE of 0.91%.…”

Section: Resultsmentioning

confidence: 99%

“…1, was developed in our previous work by introducing an asymmetric alkyl substituent. 13 Spin-casting of the resultant polymer from a chloroform solution yielded a continuous film with an E g value of 1.85 eV and good hole transport. Furthermore, it was found that introducing fluorine into the phenylene part of PhDOT can effectively lower the highest occupied molecular orbital (HOMO) of the polymer without a large change in E g .…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Organic Photovoltaics Based on Poly(3,4-phenylenedioxy-2,5-thienylenevinylene)s

2017

Self Cite

View full text Add to dashboard Cite

Poly(3,4-phenylenedioxy-2,5-thienylenevinylene)s with a fluorine substituent at the phenylene moiety (PPhDOTFV) and without the substituent (PPhDOTV) were synthesized by Stille coupling polymerization. They exhibited good solubility in common organic solvents owing to a branched alkyl chain at the phenylene moiety and a narrow optical bandgap of 1.66 eV due to an increased conjugated length caused by the vinylene bridge. Both the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of PPhDOTFV were 0.2 eV deeper than those of PPhDOTV. Organic photovoltaic cells (OPVs) using PPhDOTV:PC 70 BM exhibited a short-circuit current density (J sc ) of 3.30 mA cm , an open-circuit voltage (V oc ) of 0.52 V, and a power conversion efficiency of 0.91%, as compared to 1.62 mA cm −2 , 0.68 V, and 0.45%, respectively, for OPVs using PPhDOTFV:PC 70 BM. The J sc value of PPhDOTV-based OPVs was higher than that of PPhDOTFV-based OPVs because of a large LUMO energy offset between PPhDOTV and PC 70 BM. On the other hand, the V oc value of PPhDOTV-based OPVs was lower than that of PPhDOTFV-based OPVs because of a small energy difference between the HOMO level of PPhDOTV and the LUMO level of PC 70 BM.

show abstract

Section: Synthesis and Fundamental Properties Of Pphdotv Andmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Organic Photovoltaics Based on Poly(3,4-phenylenedioxy-2,5-thienylenevinylene)s

2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…The maximum inclination angle is called sliding angle (α). If the water droplets do not move, the water adhesion is extremely strong and the surface is completely sticky …”

Section: Methodsmentioning

confidence: 99%

“…Having somewhat higher oxidation potential (by ca. 0.3–0.4 V) than PEDOT , pPheDOT is more environmentally stable in its undoped state, and the side‐chain benzene ring in PheDOT allows additional modification of the polymer structure . Thus, Reynolds et al .…”

Section: Introductionmentioning

confidence: 99%

A Templateless Electropolymerization Approach to Porous Hydrophobic Nanostructures Using 3,4‐Phenylenedioxythiophene Monomers with Electron‐Withdrawing Groups

et al. 2018

View full text Add to dashboard Cite

Controlling the surface structures of conducting polymers is extremely important for various applications not only because of their unique optoelectronic properties but also owing to the wetting properties of these materials. Using a templateless electropolymerization approach, we report the formation of porous polymer nanostructures from a series of 3,4-(1,2-phenylenedioxy)(PheDOT) derivatives with electronwithdrawing side groups (Cl, CN, CF 3 , SO 2 CH 3 ). In this templateless electropolymerization, trace water present in solution is sufficient to produce gas bubbles (O 2 and H 2 ) and, as a consequence, to form the porous nanostructures with a tendency to form nanotubes on the surface. We show that the substituents in PheDOT play an important role to control the porous nanostructures and, as a consequence, the surface hydrophobicity. Using 3,4-(1,3-propylenedioxy)type (ProDOT) derivative F 4 -BnDOT, the formation of densely packed nanofibers was demonstrated, and these are not a result of the presence of trace water. In this case, the surfaces are even more hydrophobic than for PheDOT-based polymers, displaying extremely high apparent water contact angles (q w = 138-1448) and strong water adhesion. Such surfaces from electropolymerized conducting polymers could be used in a number of technological applications, e.g. self-cleaning surfaces, micropatterning, water harvesting and microfluid systems.

show abstract

A Templateless Electropolymerization Approach to Nanorings Using Substituted 3,4‐Naphthalenedioxythiophene (NaPhDOT) Monomers

et al. 2017

View full text Add to dashboard Cite

The formation of highly ordered surface structures is fundamental for various applications. Due to their rapidity of implementation and their cost, templateless processes are extremely interesting alternatives to the use of templates or lithographic processes. With the aim to prepare porous structures such as nanotubes, templateless electropolymerization was found to be a unique process. Based on previous works, we have synthesized 3,4-naphthalenedioxythiophene (NaPhDOT) monomers substituted with alkyl chains (n = 2 to 10), phenyl and naphthalene substituents. In particular, NaphDOT substituted with naphthalene (NaphDOTÀNa) leads for the first time to relatively densely packed nanorings while their internal diameter is controllable with the number of deposition scans. Compared to previous works, which lead to nanotubes from non-substituted NaphDOT and 3,4-phenylenedioxythiophene substituted with naphthalene (PheDOTÀNa), with NaphDOTÀNa we observe a very important decrease in the polymer growth. As a consequence, only the initial peripherical nucleation around the gas bubbles is possible, leading to nanorings, because their growth into nanotubes is impeded by their low conductivity.

show abstract

Synthesis and characterization of soluble poly(3,4-phenylenedioxythiophene)

Cited by 9 publications

References 34 publications

Organic Photovoltaics Based on Poly(3,4-phenylenedioxy-2,5-thienylenevinylene)s

Organic Photovoltaics Based on Poly(3,4-phenylenedioxy-2,5-thienylenevinylene)s

A Templateless Electropolymerization Approach to Porous Hydrophobic Nanostructures Using 3,4‐Phenylenedioxythiophene Monomers with Electron‐Withdrawing Groups

A Templateless Electropolymerization Approach to Nanorings Using Substituted 3,4‐Naphthalenedioxythiophene (NaPhDOT) Monomers

Contact Info

Product

Resources

About