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

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 cm 2/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 cm 2/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:
 [1] ;  [1] ;  [2] ;  [3] ;  [1] ;  [4] ;  [4] ;  [1] ;  [2] ;  [1]
  1. Johannes Kepler University, Linz (Austria) Linz Institute for Organic Solar Cells (LIOS)
  2. Harvard Univ., Cambridge, MA (United States)
  3. Johannes Kepler University, Linz (Austria)
  4. Polish Academy of Sciences (PAS), Warsaw (Poland). Inst. of Organic Chemistry
Publication Date:
Grant/Contract Number:
SC0008733
Type:
Published Article
Journal Name:
Organic Electronics
Additional Journal Information:
Journal Volume: 15; Journal Issue: 12; Journal ID: ISSN 1566-1199
Publisher:
Elsevier
Research Org:
Johannes Kepler Univ., Linz (Austria)
Sponsoring Org:
USDOE
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; Organic pigments; Organic field-effect transistors; Diketopyrrolopyrrole; Hydrogen-bonding; DFT calculations
OSTI Identifier:
1198126
Alternate Identifier(s):
OSTI ID: 1454533

Glowacki, Eric Daniel, Coskun, Halime, Blood-Forsythe, Martin A., Monkowius, Uwe, Leonat, Lucia, Grzybowski, Marek, Gryko, Daniel, White, Matthew Schuette, Aspuru-Guzik, Alan, and Sariciftci, Niyazi Serdar. Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors. United States: N. p., Web. doi:10.1016/j.orgel.2014.09.038.
Glowacki, Eric Daniel, Coskun, Halime, Blood-Forsythe, Martin A., Monkowius, Uwe, Leonat, Lucia, Grzybowski, Marek, Gryko, Daniel, White, Matthew Schuette, Aspuru-Guzik, Alan, & Sariciftci, Niyazi Serdar. Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors. United States. doi:10.1016/j.orgel.2014.09.038.
Glowacki, Eric Daniel, Coskun, Halime, Blood-Forsythe, Martin A., Monkowius, Uwe, Leonat, Lucia, Grzybowski, Marek, Gryko, Daniel, White, Matthew Schuette, Aspuru-Guzik, Alan, and Sariciftci, Niyazi Serdar. 2014. "Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors". United States. doi:10.1016/j.orgel.2014.09.038.
@article{osti_1198126,
title = {Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors},
author = {Glowacki, 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, Alan 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 = {United States},
year = {2014},
month = {10}
}