Impact of Singly Occupied Molecular Orbital Energy on the n-Doping Efficiency of Benzimidazole Derivatives

Sergi Riera-Galindo; Alessio Orbelli Biroli; Alessandra Forni; Yuttapoom Puttisong; Francesca Tessore; Maddalena Pizzotti; Eleni Pavlopoulou; Eduardo Solano; Suhao Wang; Gang Wang; Tero Petri Ruoko; Weimin M. Chen; Martijn Kemerink; Magnus Berggren; Gabriele Di Carlo; Simone Fabiano

doi:10.1021/acsami.9b12441

Impact of Singly Occupied Molecular Orbital Energy on the n-Doping Efficiency of Benzimidazole Derivatives

Sergi Riera-Galindo, Alessio Orbelli Biroli, Alessandra Forni, Yuttapoom Puttisong, Francesca Tessore, Maddalena Pizzotti, Eleni Pavlopoulou, Eduardo Solano, Suhao Wang, Gang Wang, Tero Petri Ruoko, Weimin M. Chen, Martijn Kemerink, Magnus Berggren, Gabriele Di Carlo, Simone Fabiano

Research output: Contribution to journal › Article › Scientific › peer-review

24 Citations (Scopus)

Abstract

We investigated the impact of singly occupied molecular orbital (SOMO) energy on the n-doping efficiency of benzimidazole derivatives. By designing and synthesizing a series of new air-stable benzimidazole-based dopants with different SOMO energy levels, we demonstrated that an increase of the dopant SOMO energy by only &tild;0.3 eV enhances the electrical conductivity of a benchmark electron-transporting naphthalenediimide-bithiophene polymer by more than 1 order of magnitude. By combining electrical, X-ray diffraction, and electron paramagnetic resonance measurements with density functional theory calculations and analytical transport simulations, we quantitatively characterized the conductivity, Seebeck coefficient, spin density, and crystallinity of the doped polymer as a function of the dopant SOMO energy. Our findings strongly indicate that charge and energy transport are dominated by the (relative) position of the SOMO level, whereas morphological differences appear to play a lesser role. These results set molecular-design guidelines for next-generation n-type dopants.

Original language	English
Pages (from-to)	37981-37990
Number of pages	10
Journal	ACS Applied Materials and Interfaces
Volume	11
Issue number	41
DOIs	https://doi.org/10.1021/acsami.9b12441
Publication status	Published - 16 Oct 2019
Externally published	Yes
Publication type	A1 Journal article-refereed

Keywords

DMBI
electron transfer
n-doped polymers
n-type dopants
SOMO energy

ASJC Scopus subject areas

Materials Science(all)

Access to Document

10.1021/acsami.9b12441

Cite this

Riera-Galindo, S., Orbelli Biroli, A., Forni, A., Puttisong, Y., Tessore, F., Pizzotti, M., Pavlopoulou, E., Solano, E., Wang, S., Wang, G., Ruoko, T. P., Chen, W. M., Kemerink, M., Berggren, M., Di Carlo, G., & Fabiano, S. (2019). Impact of Singly Occupied Molecular Orbital Energy on the n-Doping Efficiency of Benzimidazole Derivatives. ACS Applied Materials and Interfaces, 11(41), 37981-37990. https://doi.org/10.1021/acsami.9b12441

@article{fe7d681c4a224d1a8df0e5d4293eb8ff,

title = "Impact of Singly Occupied Molecular Orbital Energy on the n-Doping Efficiency of Benzimidazole Derivatives",

abstract = "We investigated the impact of singly occupied molecular orbital (SOMO) energy on the n-doping efficiency of benzimidazole derivatives. By designing and synthesizing a series of new air-stable benzimidazole-based dopants with different SOMO energy levels, we demonstrated that an increase of the dopant SOMO energy by only &tild;0.3 eV enhances the electrical conductivity of a benchmark electron-transporting naphthalenediimide-bithiophene polymer by more than 1 order of magnitude. By combining electrical, X-ray diffraction, and electron paramagnetic resonance measurements with density functional theory calculations and analytical transport simulations, we quantitatively characterized the conductivity, Seebeck coefficient, spin density, and crystallinity of the doped polymer as a function of the dopant SOMO energy. Our findings strongly indicate that charge and energy transport are dominated by the (relative) position of the SOMO level, whereas morphological differences appear to play a lesser role. These results set molecular-design guidelines for next-generation n-type dopants.",

keywords = "DMBI, electron transfer, n-doped polymers, n-type dopants, SOMO energy",

author = "Sergi Riera-Galindo and {Orbelli Biroli}, Alessio and Alessandra Forni and Yuttapoom Puttisong and Francesca Tessore and Maddalena Pizzotti and Eleni Pavlopoulou and Eduardo Solano and Suhao Wang and Gang Wang and Ruoko, {Tero Petri} and Chen, {Weimin M.} and Martijn Kemerink and Magnus Berggren and {Di Carlo}, Gabriele and Simone Fabiano",

note = "Funding Information: The authors acknowledge the Swedish Foundation for Strategic Research, VINNOVA (2015-04859), the Swedish Research Council (2016-03979), {\AA}Forsk (18-313), and the Advanced Functional Materials Center at Link{\"o}ping University (2009-00971). GIWAXS experiments were performed at the NCD-SWEET beamline of ALBA synchrotron with the collaboration of ALBA staff. Regione Lombardia and Fondazione Cariplo are gratefully acknowledged for financial support and for the use of instrumentations purchased through the SmartMatLab Centre project (2014-42639194). The authors acknowledge Serena Cappelli for DSC and TGA analysis. G.D.C. greatly thanks the Universit{\`a} degli Studi di Milano (Piano Sostegno alla Ricerca 2018 LINEA 2 Azione A—Giovani Ricercatori) for financial support. T.-P.R. acknowledges support from the Finnish Cultural Foundation. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = oct,

day = "16",

doi = "10.1021/acsami.9b12441",

language = "English",

volume = "11",

pages = "37981--37990",

number = "41",

}

Riera-Galindo, S, Orbelli Biroli, A, Forni, A, Puttisong, Y, Tessore, F, Pizzotti, M, Pavlopoulou, E, Solano, E, Wang, S, Wang, G, Ruoko, TP, Chen, WM, Kemerink, M, Berggren, M, Di Carlo, G & Fabiano, S 2019, 'Impact of Singly Occupied Molecular Orbital Energy on the n-Doping Efficiency of Benzimidazole Derivatives', ACS Applied Materials and Interfaces, vol. 11, no. 41, pp. 37981-37990. https://doi.org/10.1021/acsami.9b12441

TY - JOUR

T1 - Impact of Singly Occupied Molecular Orbital Energy on the n-Doping Efficiency of Benzimidazole Derivatives

AU - Riera-Galindo, Sergi

AU - Orbelli Biroli, Alessio

AU - Forni, Alessandra

AU - Puttisong, Yuttapoom

AU - Tessore, Francesca

AU - Pizzotti, Maddalena

AU - Pavlopoulou, Eleni

AU - Solano, Eduardo

AU - Wang, Suhao

AU - Wang, Gang

AU - Ruoko, Tero Petri

AU - Chen, Weimin M.

AU - Kemerink, Martijn

AU - Berggren, Magnus

AU - Di Carlo, Gabriele

AU - Fabiano, Simone

N1 - Funding Information: The authors acknowledge the Swedish Foundation for Strategic Research, VINNOVA (2015-04859), the Swedish Research Council (2016-03979), ÅForsk (18-313), and the Advanced Functional Materials Center at Linköping University (2009-00971). GIWAXS experiments were performed at the NCD-SWEET beamline of ALBA synchrotron with the collaboration of ALBA staff. Regione Lombardia and Fondazione Cariplo are gratefully acknowledged for financial support and for the use of instrumentations purchased through the SmartMatLab Centre project (2014-42639194). The authors acknowledge Serena Cappelli for DSC and TGA analysis. G.D.C. greatly thanks the Università degli Studi di Milano (Piano Sostegno alla Ricerca 2018 LINEA 2 Azione A—Giovani Ricercatori) for financial support. T.-P.R. acknowledges support from the Finnish Cultural Foundation. Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/10/16

Y1 - 2019/10/16

N2 - We investigated the impact of singly occupied molecular orbital (SOMO) energy on the n-doping efficiency of benzimidazole derivatives. By designing and synthesizing a series of new air-stable benzimidazole-based dopants with different SOMO energy levels, we demonstrated that an increase of the dopant SOMO energy by only &tild;0.3 eV enhances the electrical conductivity of a benchmark electron-transporting naphthalenediimide-bithiophene polymer by more than 1 order of magnitude. By combining electrical, X-ray diffraction, and electron paramagnetic resonance measurements with density functional theory calculations and analytical transport simulations, we quantitatively characterized the conductivity, Seebeck coefficient, spin density, and crystallinity of the doped polymer as a function of the dopant SOMO energy. Our findings strongly indicate that charge and energy transport are dominated by the (relative) position of the SOMO level, whereas morphological differences appear to play a lesser role. These results set molecular-design guidelines for next-generation n-type dopants.

AB - We investigated the impact of singly occupied molecular orbital (SOMO) energy on the n-doping efficiency of benzimidazole derivatives. By designing and synthesizing a series of new air-stable benzimidazole-based dopants with different SOMO energy levels, we demonstrated that an increase of the dopant SOMO energy by only &tild;0.3 eV enhances the electrical conductivity of a benchmark electron-transporting naphthalenediimide-bithiophene polymer by more than 1 order of magnitude. By combining electrical, X-ray diffraction, and electron paramagnetic resonance measurements with density functional theory calculations and analytical transport simulations, we quantitatively characterized the conductivity, Seebeck coefficient, spin density, and crystallinity of the doped polymer as a function of the dopant SOMO energy. Our findings strongly indicate that charge and energy transport are dominated by the (relative) position of the SOMO level, whereas morphological differences appear to play a lesser role. These results set molecular-design guidelines for next-generation n-type dopants.

KW - DMBI

KW - electron transfer

KW - n-doped polymers

KW - n-type dopants

KW - SOMO energy

U2 - 10.1021/acsami.9b12441

DO - 10.1021/acsami.9b12441

M3 - Article

C2 - 31539222

AN - SCOPUS:85073115227

VL - 11

SP - 37981

EP - 37990

IS - 41

ER -

Impact of Singly Occupied Molecular Orbital Energy on the n-Doping Efficiency of Benzimidazole Derivatives

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this