Modulating the ground state, stability and charge transport in OFETs of biradicaloid hexahydro-diindenopyrene derivatives and a proposed method to estimate the biradical character
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 a few examples have been reported as active layers in organic field-effect transistors (OFETs) with a charge mobil...
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| Published in | Chemical science (Cambridge) Vol. 11; no. 44; pp. 12194 - 1225 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
01.01.2020
Royal Society of Chemistry The Royal Society of Chemistry |
| Subjects | |
| Online Access | Get full text |
| ISSN | 2041-6520 2041-6539 |
| DOI | 10.1039/d0sc04583g |
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| 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 a few examples have been reported as active layers in organic field-effect transistors (OFETs) with a charge mobility of around 10
−3
cm
2
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 (
y
0
) but also the value of the singlet-triplet energy gap (Δ
E
S-T
) that does not follow the reverse trend of
y
0
. A method based on comparison between experimental and theoretical bond lengths has been disclosed to estimate
y
0
and shows that
y
0
computed at the projected unrestricted Hartree-Fock (PUHF) level is the most relevant among those reported by all other methods. Thanks to their high stability, thin-film OFETs were successfully fabricated. Well balanced ambipolar transport was obtained in the order of 10
−3
cm
2
V
−1
s
−1
in the bottom-gate/top-contact configuration, and unipolar transport in the top-gate/bottom-contact configuration was obtained in the order of 10
−1
cm
2
V
−1
s
−1
which is the highest value obtained for biradical compounds with a diindenoacene skeleton.
Biradicaloid HDIP derivatives show that the Δ
E
S-T
gap does not follow the reverse trend of the biradical character but depends more on the delocalization of the radical centres at the outer rings. |
|---|---|
| AbstractList | 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 OFETs with charge mobility of around 10 −3 cm 2 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 TIPS-ethynyl groups. All the HDIP derivatives show remarkably higher stability than that of triisopropylsilyl (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 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 cm 2 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 cm 2 V −1 s −1 which is the highest value obtained for biradical compounds with a diindenoacene skeleton. 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 a few examples have been reported as active layers in organic field-effect transistors (OFETs) with a charge mobility of around 10 −3 cm 2 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 ( y 0 ) but also the value of the singlet-triplet energy gap (Δ E S-T ) that does not follow the reverse trend of y 0 . A method based on comparison between experimental and theoretical bond lengths has been disclosed to estimate y 0 and shows that y 0 computed at the projected unrestricted Hartree-Fock (PUHF) level is the most relevant among those reported by all other methods. Thanks to their high stability, thin-film OFETs were successfully fabricated. Well balanced ambipolar transport was obtained in the order of 10 −3 cm 2 V −1 s −1 in the bottom-gate/top-contact configuration, and unipolar transport in the top-gate/bottom-contact configuration was obtained in the order of 10 −1 cm 2 V −1 s −1 which is the highest value obtained for biradical compounds with a diindenoacene skeleton. Biradicaloid HDIP derivatives show that the Δ E S-T gap does not follow the reverse trend of the biradical character but depends more on the delocalization of the radical centres at the outer rings. 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 a few examples have been reported as active layers in organic field-effect transistors (OFETs) with a charge mobility of around 10 −3 cm 2 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 ( y 0 ) but also the value of the singlet–triplet energy gap (Δ E S–T ) that does not follow the reverse trend of y 0 . A method based on comparison between experimental and theoretical bond lengths has been disclosed to estimate y 0 and shows that y 0 computed at the projected unrestricted Hartree–Fock (PUHF) level is the most relevant among those reported by all other methods. Thanks to their high stability, thin-film OFETs were successfully fabricated. Well balanced ambipolar transport was obtained in the order of 10 −3 cm 2 V −1 s −1 in the bottom-gate/top-contact configuration, and unipolar transport in the top-gate/bottom-contact configuration was obtained in the order of 10 −1 cm 2 V −1 s −1 which is the highest value obtained for biradical compounds with a diindenoacene skeleton. 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 a few examples have been reported as active layers in organic field-effect transistors (OFETs) with a 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 (y 0) but also the value of the singlet-triplet energy gap (ΔE S-T) that does not follow the reverse trend of y 0. A method based on comparison between experimental and theoretical bond lengths has been disclosed to estimate y 0 and shows that y 0 computed at the projected unrestricted Hartree-Fock (PUHF) level is the most relevant among those reported by all other methods. Thanks to their 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 the 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.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 a few examples have been reported as active layers in organic field-effect transistors (OFETs) with a 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 (y 0) but also the value of the singlet-triplet energy gap (ΔE S-T) that does not follow the reverse trend of y 0. A method based on comparison between experimental and theoretical bond lengths has been disclosed to estimate y 0 and shows that y 0 computed at the projected unrestricted Hartree-Fock (PUHF) level is the most relevant among those reported by all other methods. Thanks to their 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 the 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. 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 a few examples have been reported as active layers in organic field-effect transistors (OFETs) with a charge mobility of around 10(-3) cm(2) 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 (y(0)) but also the value of the singlet-triplet energy gap (Delta ES-T) that does not follow the reverse trend of y(0). A method based on comparison between experimental and theoretical bond lengths has been disclosed to estimate y(0) and shows that y(0) computed at the projected unrestricted Hartree-Fock (PUHF) level is the most relevant among those reported by all other methods. Thanks to their high stability, thin-film OFETs were successfully fabricated. Well balanced ambipolar transport was obtained in the order of 10(-3) cm(2) V-1 s(-1) in the bottom-gate/top-contact configuration, and unipolar transport in the top-gate/bottom-contact configuration was obtained in the order of 10(-1) cm(2) V-1 s(-1) which is the highest value obtained for biradical compounds with a diindenoacene skeleton. 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 a few examples have been reported as active layers in organic field-effect transistors (OFETs) with a 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 the singlet–triplet energy gap (ΔES–T) that does not follow the reverse trend of y0. A method based on comparison between experimental and theoretical bond lengths has been disclosed to estimate y0 and shows that y0 computed at the projected unrestricted Hartree–Fock (PUHF) level is the most relevant among those reported by all other methods. Thanks to their 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 the 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. |
| Author | Marrot, Jérome Okazawa, Atsushi Mamada, Masashi Ishida, Takayuki Yassar, Abderrahim Adachi, Chihaya Frigoli, Michel Jousselin-Oba, Tanguy |
| AuthorAffiliation | Center for Organic Photonics and Electronics Research (OPERA) Academia-Industry Molecular Systems for Devices Research and Education Center Institute of Liberal Education Université Paris-Saclay International Institute for Carbon Neutral Energy Research (WPI-I2CNER) Institut Polytechnique de Paris Kyushu University Division of Chemistry Department of Engineering Science The University of Electro-Communications CNRS JST ERATO Adachi Molecular Exciton Engineering Project UVSQ Institut Lavoisier de Versailles Ecole Polytechnique LPICM UMR CNRS 8180 Nihon University School of Medicine |
| AuthorAffiliation_xml | – name: Nihon University School of Medicine – name: Kyushu University – name: The University of Electro-Communications – name: CNRS – name: Academia-Industry Molecular Systems for Devices Research and Education Center – name: UMR CNRS 8180 – name: Institut Lavoisier de Versailles – name: Université Paris-Saclay – name: Department of Engineering Science – name: Center for Organic Photonics and Electronics Research (OPERA) – name: Institute of Liberal Education – name: UVSQ – name: Division of Chemistry – name: LPICM – name: International Institute for Carbon Neutral Energy Research (WPI-I2CNER) – name: Institut Polytechnique de Paris – name: Ecole Polytechnique – name: JST ERATO Adachi Molecular Exciton Engineering Project |
| Author_xml | – sequence: 1 givenname: Tanguy surname: Jousselin-Oba fullname: Jousselin-Oba, Tanguy – sequence: 2 givenname: Masashi surname: Mamada fullname: Mamada, Masashi – sequence: 3 givenname: Atsushi surname: Okazawa fullname: Okazawa, Atsushi – sequence: 4 givenname: Jérome surname: Marrot fullname: Marrot, Jérome – sequence: 5 givenname: Takayuki surname: Ishida fullname: Ishida, Takayuki – sequence: 6 givenname: Chihaya surname: Adachi fullname: Adachi, Chihaya – sequence: 7 givenname: Abderrahim surname: Yassar fullname: Yassar, Abderrahim – sequence: 8 givenname: Michel surname: Frigoli fullname: Frigoli, Michel |
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| Publisher | Royal Soc Chemistry Royal Society of Chemistry The Royal Society of Chemistry |
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| Snippet | 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... |
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| SubjectTerms | Charge transport Chemical Sciences Chemistry Chemistry, Multidisciplinary Configurations Crystallography Derivatives Energy gap Field effect transistors Ground state Oxidation Physical Sciences Physics Science & Technology Semiconductor devices Stability Thin films |
| Title | Modulating the ground state, stability and charge transport in OFETs of biradicaloid hexahydro-diindenopyrene derivatives and a proposed method to estimate the biradical character |
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