Introducing Solubility Control for Improved Organic P-Type Dopants

Jun Li, Guangwu Zhang, Daniella M. Holm, Ian E. Jacobs, Bin Yin, Pieter Stroeve, Mark Mascal, Adam J. Moulé

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

To overcome the poor solubility of the widely used p-type dopant 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), we have synthesized a series of structure-modified, organic p-type dopants to include alkyl ester groups designed to enable solubility and miscibility control. UV-vis-NIR and cyclic voltammetry measurements show increased solubility of mono- and diester substituted dopants with only modest changes to acceptor strength. Using absorption spectroscopy, photoluminescence, and in-plane conductivity measurements, we demonstrate that the new dopants can successfully p-type dope poly(3-hexylthiophene-2,5-diyl) (P3HT). Monoester substituted dopants are characterized by only slightly reduced electron affinity relative to F4TCNQ, but greater doping effectiveness due to increased miscibility with P3HT. Diester substituted dopants undergo a dimerization reaction before assuming their doped states, which may help anchor dopants into position post deposition, thus decreasing the negative effect of dopant drift and diffusion. We conclude that increased dopant solubility/miscibility increases the overall effectiveness of doping in solution-cast polymer films and that ester modification is a practical approach to achieving solubility/miscibility control in TCNQ-type dopants (Figure Presented).

Original languageEnglish (US)
Pages (from-to)5765-5774
Number of pages10
JournalChemistry of Materials
Volume27
Issue number16
DOIs
StatePublished - Aug 25 2015

Fingerprint

Solubility
Doping (additives)
Esters
Electron affinity
Dimerization
Anchors
Absorption spectroscopy
Polymer films
Cyclic voltammetry
Photoluminescence

ASJC Scopus subject areas

  • Materials Chemistry
  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Li, J., Zhang, G., Holm, D. M., Jacobs, I. E., Yin, B., Stroeve, P., ... Moulé, A. J. (2015). Introducing Solubility Control for Improved Organic P-Type Dopants. Chemistry of Materials, 27(16), 5765-5774. https://doi.org/10.1021/acs.chemmater.5b02340

Introducing Solubility Control for Improved Organic P-Type Dopants. / Li, Jun; Zhang, Guangwu; Holm, Daniella M.; Jacobs, Ian E.; Yin, Bin; Stroeve, Pieter; Mascal, Mark; Moulé, Adam J.

In: Chemistry of Materials, Vol. 27, No. 16, 25.08.2015, p. 5765-5774.

Research output: Contribution to journalArticle

Li, J, Zhang, G, Holm, DM, Jacobs, IE, Yin, B, Stroeve, P, Mascal, M & Moulé, AJ 2015, 'Introducing Solubility Control for Improved Organic P-Type Dopants', Chemistry of Materials, vol. 27, no. 16, pp. 5765-5774. https://doi.org/10.1021/acs.chemmater.5b02340
Li J, Zhang G, Holm DM, Jacobs IE, Yin B, Stroeve P et al. Introducing Solubility Control for Improved Organic P-Type Dopants. Chemistry of Materials. 2015 Aug 25;27(16):5765-5774. https://doi.org/10.1021/acs.chemmater.5b02340
Li, Jun ; Zhang, Guangwu ; Holm, Daniella M. ; Jacobs, Ian E. ; Yin, Bin ; Stroeve, Pieter ; Mascal, Mark ; Moulé, Adam J. / Introducing Solubility Control for Improved Organic P-Type Dopants. In: Chemistry of Materials. 2015 ; Vol. 27, No. 16. pp. 5765-5774.
@article{0cc85a0ad930430ea4c3987ee534bbb9,
title = "Introducing Solubility Control for Improved Organic P-Type Dopants",
abstract = "To overcome the poor solubility of the widely used p-type dopant 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), we have synthesized a series of structure-modified, organic p-type dopants to include alkyl ester groups designed to enable solubility and miscibility control. UV-vis-NIR and cyclic voltammetry measurements show increased solubility of mono- and diester substituted dopants with only modest changes to acceptor strength. Using absorption spectroscopy, photoluminescence, and in-plane conductivity measurements, we demonstrate that the new dopants can successfully p-type dope poly(3-hexylthiophene-2,5-diyl) (P3HT). Monoester substituted dopants are characterized by only slightly reduced electron affinity relative to F4TCNQ, but greater doping effectiveness due to increased miscibility with P3HT. Diester substituted dopants undergo a dimerization reaction before assuming their doped states, which may help anchor dopants into position post deposition, thus decreasing the negative effect of dopant drift and diffusion. We conclude that increased dopant solubility/miscibility increases the overall effectiveness of doping in solution-cast polymer films and that ester modification is a practical approach to achieving solubility/miscibility control in TCNQ-type dopants (Figure Presented).",
author = "Jun Li and Guangwu Zhang and Holm, {Daniella M.} and Jacobs, {Ian E.} and Bin Yin and Pieter Stroeve and Mark Mascal and Moul{\'e}, {Adam J.}",
year = "2015",
month = "8",
day = "25",
doi = "10.1021/acs.chemmater.5b02340",
language = "English (US)",
volume = "27",
pages = "5765--5774",
journal = "Chemistry of Materials",
issn = "0897-4756",
publisher = "American Chemical Society",
number = "16",

}

TY - JOUR

T1 - Introducing Solubility Control for Improved Organic P-Type Dopants

AU - Li, Jun

AU - Zhang, Guangwu

AU - Holm, Daniella M.

AU - Jacobs, Ian E.

AU - Yin, Bin

AU - Stroeve, Pieter

AU - Mascal, Mark

AU - Moulé, Adam J.

PY - 2015/8/25

Y1 - 2015/8/25

N2 - To overcome the poor solubility of the widely used p-type dopant 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), we have synthesized a series of structure-modified, organic p-type dopants to include alkyl ester groups designed to enable solubility and miscibility control. UV-vis-NIR and cyclic voltammetry measurements show increased solubility of mono- and diester substituted dopants with only modest changes to acceptor strength. Using absorption spectroscopy, photoluminescence, and in-plane conductivity measurements, we demonstrate that the new dopants can successfully p-type dope poly(3-hexylthiophene-2,5-diyl) (P3HT). Monoester substituted dopants are characterized by only slightly reduced electron affinity relative to F4TCNQ, but greater doping effectiveness due to increased miscibility with P3HT. Diester substituted dopants undergo a dimerization reaction before assuming their doped states, which may help anchor dopants into position post deposition, thus decreasing the negative effect of dopant drift and diffusion. We conclude that increased dopant solubility/miscibility increases the overall effectiveness of doping in solution-cast polymer films and that ester modification is a practical approach to achieving solubility/miscibility control in TCNQ-type dopants (Figure Presented).

AB - To overcome the poor solubility of the widely used p-type dopant 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), we have synthesized a series of structure-modified, organic p-type dopants to include alkyl ester groups designed to enable solubility and miscibility control. UV-vis-NIR and cyclic voltammetry measurements show increased solubility of mono- and diester substituted dopants with only modest changes to acceptor strength. Using absorption spectroscopy, photoluminescence, and in-plane conductivity measurements, we demonstrate that the new dopants can successfully p-type dope poly(3-hexylthiophene-2,5-diyl) (P3HT). Monoester substituted dopants are characterized by only slightly reduced electron affinity relative to F4TCNQ, but greater doping effectiveness due to increased miscibility with P3HT. Diester substituted dopants undergo a dimerization reaction before assuming their doped states, which may help anchor dopants into position post deposition, thus decreasing the negative effect of dopant drift and diffusion. We conclude that increased dopant solubility/miscibility increases the overall effectiveness of doping in solution-cast polymer films and that ester modification is a practical approach to achieving solubility/miscibility control in TCNQ-type dopants (Figure Presented).

UR - http://www.scopus.com/inward/record.url?scp=84940093544&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84940093544&partnerID=8YFLogxK

U2 - 10.1021/acs.chemmater.5b02340

DO - 10.1021/acs.chemmater.5b02340

M3 - Article

AN - SCOPUS:84940093544

VL - 27

SP - 5765

EP - 5774

JO - Chemistry of Materials

JF - Chemistry of Materials

SN - 0897-4756

IS - 16

ER -