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Title: Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors

Abstract

Diketopyrrolopyrroles (DPPs) have recently gained attention as building-blocks for organic semiconducting polymers and small molecules, however the semiconducting properties of their hydrogen-bonded (H-bonded) pigment forms have not been explored. Herein we report on the performance of three archetypical H-bonded DPP pigments, which show ambipolar carrier mobilities in the range 0.01–0.06 cm2/V s in organic field-effect transistors. Their semiconducting properties are correlated with crystal structure, where an H-bonded crystal lattice supports close and relatively cofacial π–π stacking. To better understand transport in these systems, density functional theory calculations were carried out, indicating theoretical maximum ambipolar mobility values of ~0.3 cm2/V s. Furthermore, based on these experimental and theoretical results, H-bonded DPPs represent a viable alternative to more established DPP-containing polymers and small molecules where H-bonding is blocked by N-alkylation.

Authors:
; ; ; ; ; ; ; ; ;
Publication Date:
Research Org.:
Johannes Kepler Univ., Linz (Austria)
Sponsoring Org.:
USDOE
OSTI Identifier:
1198126
Alternate Identifier(s):
OSTI ID: 1454533
Grant/Contract Number:  
SC0008733
Resource Type:
Published Article
Journal Name:
Organic Electronics
Additional Journal Information:
Journal Name: Organic Electronics Journal Volume: 15 Journal Issue: 12; Journal ID: ISSN 1566-1199
Publisher:
Elsevier
Country of Publication:
Netherlands
Language:
English
Subject:
36 MATERIALS SCIENCE; Organic pigments; Organic field-effect transistors; Diketopyrrolopyrrole; Hydrogen-bonding; DFT calculations

Citation Formats

Głowacki, Eric Daniel, Coskun, Halime, Blood-Forsythe, Martin A., Monkowius, Uwe, Leonat, Lucia, Grzybowski, Marek, Gryko, Daniel, White, Matthew Schuette, Aspuru-Guzik, Alán, and Sariciftci, Niyazi Serdar. Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors. Netherlands: N. p., 2014. Web. doi:10.1016/j.orgel.2014.09.038.
Głowacki, Eric Daniel, Coskun, Halime, Blood-Forsythe, Martin A., Monkowius, Uwe, Leonat, Lucia, Grzybowski, Marek, Gryko, Daniel, White, Matthew Schuette, Aspuru-Guzik, Alán, & Sariciftci, Niyazi Serdar. Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors. Netherlands. doi:10.1016/j.orgel.2014.09.038.
Głowacki, Eric Daniel, Coskun, Halime, Blood-Forsythe, Martin A., Monkowius, Uwe, Leonat, Lucia, Grzybowski, Marek, Gryko, Daniel, White, Matthew Schuette, Aspuru-Guzik, Alán, and Sariciftci, Niyazi Serdar. Mon . "Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors". Netherlands. doi:10.1016/j.orgel.2014.09.038.
@article{osti_1198126,
title = {Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors},
author = {Głowacki, Eric Daniel and Coskun, Halime and Blood-Forsythe, Martin A. and Monkowius, Uwe and Leonat, Lucia and Grzybowski, Marek and Gryko, Daniel and White, Matthew Schuette and Aspuru-Guzik, Alán and Sariciftci, Niyazi Serdar},
abstractNote = {Diketopyrrolopyrroles (DPPs) have recently gained attention as building-blocks for organic semiconducting polymers and small molecules, however the semiconducting properties of their hydrogen-bonded (H-bonded) pigment forms have not been explored. Herein we report on the performance of three archetypical H-bonded DPP pigments, which show ambipolar carrier mobilities in the range 0.01–0.06 cm2/V s in organic field-effect transistors. Their semiconducting properties are correlated with crystal structure, where an H-bonded crystal lattice supports close and relatively cofacial π–π stacking. To better understand transport in these systems, density functional theory calculations were carried out, indicating theoretical maximum ambipolar mobility values of ~0.3 cm2/V s. Furthermore, based on these experimental and theoretical results, H-bonded DPPs represent a viable alternative to more established DPP-containing polymers and small molecules where H-bonding is blocked by N-alkylation.},
doi = {10.1016/j.orgel.2014.09.038},
journal = {Organic Electronics},
number = 12,
volume = 15,
place = {Netherlands},
year = {2014},
month = {12}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1016/j.orgel.2014.09.038

Citation Metrics:
Cited by: 36 works
Citation information provided by
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Figures / Tables:

Figure 1 Figure 1: (a) Molecular structures of the three DPP derivatives used in this paper. Red dashed lines show where hydrogen bonds are formed with neighboring molecules. (b) Schematic of the OFET devices used in this study. (For interpretation of the references to colour in this figure legend, the reader ismore » referred to the web version of this article.)« less

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Works referencing / citing this record:

CCDC 958818: Experimental Crystal Structure Determination: MUNHEK : 3,6-bis(4-Bromophenyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
dataset, May 2014

  • Głowacki, Eric Daniel; Coskun, Halime; Blood-Forsythe, Martin A.
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Epindolidiones-Versatile and Stable Hydrogen-Bonded Pigments for Organic Field-Effect Transistors and Light-Emitting Diodes
journal, December 2014

  • Głowacki, Eric Daniel; Romanazzi, Giuseppe; Yumusak, Cigdem
  • Advanced Functional Materials, Vol. 25, Issue 5
  • DOI: 10.1002/adfm.201402539

Diketopyrrolopyrrole Organic Thin-Film Transistors: Impact of Alkyl Substituents and Tolerance of Ethylhexyl Stereoisomers
journal, September 2016

  • Stolte, Matthias; Suraru, Sabin-Lucian; Diemer, Patricia
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  • DOI: 10.1002/adfm.201602994

An iodine effect in ambipolar organic field-effect transistors based on indigo derivatives
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Air-stable ambipolar organic transistors based on charge-transfer complexes containing dibenzopyrrolopyrrole
journal, January 2016

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Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials
journal, January 2017

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  • DOI: 10.1039/c6tc05076j

Biscoumarin-containing acenes as stable organic semiconductors for photocatalytic oxygen reduction to hydrogen peroxide
journal, January 2017

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  • J. Mater. Chem. A, Vol. 5, Issue 39
  • DOI: 10.1039/c7ta05882a

Tuning crystallochromism in diketopyrrolopyrrole- co -thieno[3,2- b ]thiophene derivatives by the architecture of their alkyl side chains
journal, January 2018

  • Genevaz, Nicolas; Chávez, Patricia; Untilova, Viktoriia
  • Journal of Materials Chemistry C, Vol. 6, Issue 34
  • DOI: 10.1039/c8tc02022a

Ambipolar transistors based on chloro-substituted tetraphenylpentacene
journal, January 2019

  • Sato, Ryonosuke; Eda, Shohei; Sugiyama, Haruki
  • Journal of Materials Chemistry C, Vol. 7, Issue 11
  • DOI: 10.1039/c8tc06603e

Epindolidiones-Versatile and Stable Hydrogen-Bonded Pigments for Organic Field-Effect Transistors and Light-Emitting Diodes
journal, December 2014

  • Głowacki, Eric Daniel; Romanazzi, Giuseppe; Yumusak, Cigdem
  • Advanced Functional Materials, Vol. 25, Issue 5
  • DOI: 10.1002/adfm.201402539

Diketopyrrolopyrrole Organic Thin-Film Transistors: Impact of Alkyl Substituents and Tolerance of Ethylhexyl Stereoisomers
journal, September 2016

  • Stolte, Matthias; Suraru, Sabin-Lucian; Diemer, Patricia
  • Advanced Functional Materials, Vol. 26, Issue 41
  • DOI: 10.1002/adfm.201602994

An iodine effect in ambipolar organic field-effect transistors based on indigo derivatives
journal, January 2015

  • Pitayatanakul, Oratai; Iijima, Kodai; Ashizawa, Minoru
  • Journal of Materials Chemistry C, Vol. 3, Issue 33
  • DOI: 10.1039/c5tc01023c

Air-stable ambipolar organic transistors based on charge-transfer complexes containing dibenzopyrrolopyrrole
journal, January 2016

  • Fujisue, Chika; Kadoya, Tomofumi; Higashino, Toshiki
  • RSC Advances, Vol. 6, Issue 58
  • DOI: 10.1039/c6ra10606d

Adamantane substitutions: a path to high-performing, soluble, versatile and sustainable organic semiconducting materials
journal, January 2017

  • Kovalenko, Alexander; Yumusak, Cigdem; Heinrichova, Patricie
  • Journal of Materials Chemistry C, Vol. 5, Issue 19
  • DOI: 10.1039/c6tc05076j

Biscoumarin-containing acenes as stable organic semiconductors for photocatalytic oxygen reduction to hydrogen peroxide
journal, January 2017

  • Węcławski, Marek K.; Jakešová, Marie; Charyton, Martyna
  • J. Mater. Chem. A, Vol. 5, Issue 39
  • DOI: 10.1039/c7ta05882a

Tuning crystallochromism in diketopyrrolopyrrole- co -thieno[3,2- b ]thiophene derivatives by the architecture of their alkyl side chains
journal, January 2018

  • Genevaz, Nicolas; Chávez, Patricia; Untilova, Viktoriia
  • Journal of Materials Chemistry C, Vol. 6, Issue 34
  • DOI: 10.1039/c8tc02022a

Ambipolar transistors based on chloro-substituted tetraphenylpentacene
journal, January 2019

  • Sato, Ryonosuke; Eda, Shohei; Sugiyama, Haruki
  • Journal of Materials Chemistry C, Vol. 7, Issue 11
  • DOI: 10.1039/c8tc06603e