Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.



Modulating the ground state, stability and charge transport in OFETs of biradicaloid Hexahydro-diindenopyrene derivatives and a proposed method to estimate the biradical character

Abstract

Biradicaloid compounds with an open-shell ground state have been the subject of intense research in the past decade. Although diindenoacenes are one of the most developed families, only few examples have been reported as active layer in organic field-effect transistors (OFETs) with charge mobility of around 10−3 cm2 V−1 s−1 due to a steric disadvantage of the mesityl group to kinetically stabilize compounds. Herein, we disclose our efforts to improve the charge transport of the diindenoacene family based on hexahydro-diindenopyrene (HDIP) derivatives with different annelation modes for which the most reactive position has been functionalized with (triisopropylsilyl)ethynyl (TIPS) groups. All the HDIP derivatives show remarkably higher stability than that of TIPS-pentacene, enduring for 2 days to more than 30 days, which depends on the oxidation potential, the contribution of the singlet biradical form in the ground state and the annelation mode. The annelation mode affects not only the band gap and the biradical character (y0) but also the value of singlet-triplet energy gap (ΔES-T) that does not follow the reverse trend of the y0. A method based on comparison between experimental and theoretical bond lengths has been disclosed to estimate the y0 and shows that the y0 computed at projected unrestricted Hartree-Fock (PUHF) is most relevant among all other methods. Thanks to the high stability, thin-film OFETs were successfully fabricated. Well balanced ambipolar transport was obtained in the order of 10−3 cm2 V−1 s−1 in the bottom-gate/top-contact configuration, and unipolar transport in top-gate/bottom-contact configuration was obtained in the order of 10−1 cm2 V−1 s−1 which is the highest value obtained for biradical compounds with a diindenoacene skeleton.

Back to tab navigation

Supplementary files

Article information


Submitted
20 Aug 2020
Accepted
15 Sep 2020
First published
16 Sep 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Accepted Manuscript
Article type
Edge Article

Modulating the ground state, stability and charge transport in OFETs of biradicaloid Hexahydro-diindenopyrene derivatives and a proposed method to estimate the biradical character

T. Jousselin-Oba, M. Mamada, A. Okazawa, J. Marrot, T. Ishida, C. Adachi, A. Yassar and M. Frigoli, Chem. Sci., 2020, Accepted Manuscript , DOI: 10.1039/D0SC04583G

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements