Highly conducting, soluble, and environmentally-stable poly(3-alkylthiophenes)

Jen, Alex K.‐Y.; Miller, G. G.; Elsenbaumer, Ronald L.

doi:10.1039/c39860001346

Cited by 339 publications

(124 citation statements)

References 1 publication

Supporting

Mentioning

124

Contrasting

Order By: Relevance

“…However, it has been shown that the presence of side chains lowers the melting point and makes the substituted polythiophenes soluble in most organic solvents, such as chloroform, tetrahydrofuran or toluene (Jen, Miller & Elsenbaumer, 1986;Sato, Tanaka & Kaeriyama, 1986). It seems that the presence of side chains does not greatly affect the conducting properties.…”

Section: Commentmentioning

confidence: 99%

3,3'-Bis(octyloxy)-2,2'-bithiophene at 195 K

Pelletier¹,

Brisse²,

Cloutier³

et al. 1995

Acta Crystallogr C

View full text Add to dashboard Cite

Section: Commentmentioning

confidence: 99%

3,3'-Bis(octyloxy)-2,2'-bithiophene at 195 K

Pelletier¹,

Brisse²,

Cloutier³

et al. 1995

Acta Crystallogr C

View full text Add to dashboard Cite

“…28 In some cases, the reaction between semiconductor and dopant results in the evolution of a gas, rendering the process irreversible. 29,30 Irreversible reactions are not amenable to dedoping, so for obvious reasons we restrict the present study to simple, single-electron transfer p-type doping. Here, the dopant electron affinity (EA) must be greater than the semiconductor ionization energy (IE), as is the case for P3HT:F4TCNQ.…”

Section: ■ Introductionmentioning

confidence: 99%

Quantitative Dedoping of Conductive Polymers

Jacobs¹,

Wang²,

Hafezi³

et al. 2017

Chem. Mater.

View full text Add to dashboard Cite

Although doping is a cornerstone of the inorganic semiconductor industry, most devices using organic semiconductors (OSCs) make use of intrinsic (undoped) materials. Recent work on OSC doping has focused on the use of dopants to modify a material’s physical properties, such as solubility, in addition to electronic and optical properties. However, if these effects are to be exploited in device manufacturing, a method for dedoping organic semiconductors is required. Here, we outline two chemical strategies for dedoping OSC films. In the first strategy, we use an electron donor (a tertiary amine) to act as competitive donor. This process is based on a thermodynamic equilibrium between ionization of the donor and OSC and results in only partial dedoping. In the second strategy, we use an electron donor that subsequently reacts with the p-type dopant to create a nondoping product molecule. Primary and secondary amines undergo a rapid addition reaction with the dopant molecule 2,3,5,6-tetrafluoro-7,7,8,8,-tetracyanoquinodimethane (F4TCNQ), with primary amines undergoing a further reaction eliminating HCN. Under optimized conditions, films of semiconducting polymer poly(3-hexylthiophene) (P3HT) dedoped with 1-propylamine (PA) reach as-cast fluorescence intensities within 5 s of exposure to the amine, eventually reaching 140% of the as-cast values. Field-effect mobilities similarly recover after dedoping. Quantitative fluorescence recovery is possible even in highly fluorescent polymers such as PFB, which are expected to be much more sensitive to residual dopants. Interestingly, treatment of undoped films with PA also yields increased fluorescence intensity and a reduction in conductivity of at least 2 orders of magnitude. These results indicate that the process quantitatively removes not only F4TCNQ but also intrinsic p-type impurities present in as-cast films. The dedoping strategies outlined in this article are generally applicable to other p- and n-type molecular dopants in OSC films.

show abstract

“…Alkyl-substituted polythiophenes ( Fig. 3.16) were first studied in the 1980s and the self-assembled lamellar structures in bulk were revealed using X-ray scattering [278][279][280][281][282][283]. For example, regiorandom poly(octylthiophene) shows a lamellar self-assembly at room temperature with a periodicity of approximately 2.2 nm and an order-disorder transition takes place at approximately 150 8C.…”

Section: Self-assembly Of Conjugated Polymersmentioning

confidence: 99%