Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices

Abdelkader Hlel; Saber Ghomrasni; Walid Taouali; Kamel Alimi

doi:doi:10.11648/j.ijctc.20200801.11

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Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices

Abdelkader Hlel, Saber Ghomrasni, Walid Taouali, Kamel Alimi

Published in International Journal of Computational and Theoretical Chemistry (Volume 8, Issue 1)

Received: 11 November 2019 Accepted: 3 December 2019 Published: 4 January 2020

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Abstract

In this paper, geometrical (in ground and excited states), electronic, optical and charge transfer properties, (ionization potentials (IP), electron affinities (EA) and HOMO-LUMO gaps (ΔE_H-L), as well as the lowest excitation energies (E_ex) and reorganization energies) of the phenylene-tiophene oligomers are studied by the density functional theory (DFT) and Time-dependent DFT approaches. Based on the density functional theory (DFT/B3LYP and CAM –B3LYP functional with 6-31G (d,p) basis set), we will highlight the effect of terminal acceptor/donor (CN, NO₂, and CF₃) /OCH₃, N(CH₃)₂ substituents on thiophene-phenylene derivatives. The excited state indicates more planar structures of the co-oligomers, which leads to a decrease in the (HOMO-LUMO) gap compared with the ground state, especially when the acceptor character increases. Furthermore, the vinyl spacer and cyanide ((–CN) functional group (Compound C₈) stabilize the LUMO levels of energy and improve the transport properties of the thiophene-phenylene derivatives. Comparing with the donor groups, the results show that the electron withdrawing substituents are remarkable on the energy levels of the frontier molecular orbitals, and on the transport charge proprieties in these co-oligomers. Thus, the LUMO energy levels become more stabilized for co-oligomers having more acceptor moieties and the HOMO–LUMO energy gap is reduced, therefore, the improvement of the conduction properties of these species is, then, observed. Moreover, the absorption spectra, computed in the presence or not of solvent at PCM model in chloroform, shows that the increase of acceptor character induces a red shift and important absorption intensity. The decrease injection barrier and smaller reorganization energies are revealing that our designed co-oligomers would be an efficient hole as well as electron transfer materials. The predicted values have shown that the designed derivatives would be efficient for the organic field effect transistors, photovoltaics and light emitters.

Published in	International Journal of Computational and Theoretical Chemistry (Volume 8, Issue 1)
DOI	10.11648/j.ijctc.20200801.11
Page(s)	1-10
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2020. Published by Science Publishing Group

Keywords

Thiophene-phenylene, DFT, CAM–B3LYP, B3LYP, Optical Absorption, Reorganization Energies

References

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Abdelkader Hlel, Saber Ghomrasni, Walid Taouali, Kamel Alimi. (2020). Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices. International Journal of Computational and Theoretical Chemistry, 8(1), 1-10. https://doi.org/10.11648/j.ijctc.20200801.11

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Abdelkader Hlel; Saber Ghomrasni; Walid Taouali; Kamel Alimi. Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices. Int. J. Comput. Theor. Chem. 2020, 8(1), 1-10. doi: 10.11648/j.ijctc.20200801.11

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AMA Style

Abdelkader Hlel, Saber Ghomrasni, Walid Taouali, Kamel Alimi. Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices. Int J Comput Theor Chem. 2020;8(1):1-10. doi: 10.11648/j.ijctc.20200801.11

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@article{10.11648/j.ijctc.20200801.11,
  author = {Abdelkader Hlel and Saber Ghomrasni and Walid Taouali and Kamel Alimi},
  title = {Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices},
  journal = {International Journal of Computational and Theoretical Chemistry},
  volume = {8},
  number = {1},
  pages = {1-10},
  doi = {10.11648/j.ijctc.20200801.11},
  url = {https://doi.org/10.11648/j.ijctc.20200801.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijctc.20200801.11},
  abstract = {In this paper, geometrical (in ground and excited states), electronic, optical and charge transfer properties, (ionization potentials (IP), electron affinities (EA) and HOMO-LUMO gaps (ΔEH-L), as well as the lowest excitation energies (Eex) and reorganization energies) of the phenylene-tiophene oligomers are studied by the density functional theory (DFT) and Time-dependent DFT approaches. Based on the density functional theory (DFT/B3LYP and CAM –B3LYP functional with 6-31G (d,p) basis set), we will highlight the effect of terminal acceptor/donor (CN, NO2, and CF3) /OCH3, N(CH3)2 substituents on thiophene-phenylene derivatives. The excited state indicates more planar structures of the co-oligomers, which leads to a decrease in the (HOMO-LUMO) gap compared with the ground state, especially when the acceptor character increases. Furthermore, the vinyl spacer and cyanide ((–CN) functional group (Compound C8) stabilize the LUMO levels of energy and improve the transport properties of the thiophene-phenylene derivatives. Comparing with the donor groups, the results show that the electron withdrawing substituents are remarkable on the energy levels of the frontier molecular orbitals, and on the transport charge proprieties in these co-oligomers. Thus, the LUMO energy levels become more stabilized for co-oligomers having more acceptor moieties and the HOMO–LUMO energy gap is reduced, therefore, the improvement of the conduction properties of these species is, then, observed. Moreover, the absorption spectra, computed in the presence or not of solvent at PCM model in chloroform, shows that the increase of acceptor character induces a red shift and important absorption intensity. The decrease injection barrier and smaller reorganization energies are revealing that our designed co-oligomers would be an efficient hole as well as electron transfer materials. The predicted values have shown that the designed derivatives would be efficient for the organic field effect transistors, photovoltaics and light emitters.},
 year = {2020}
}

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TY  - JOUR
T1  - Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices
AU  - Abdelkader Hlel
AU  - Saber Ghomrasni
AU  - Walid Taouali
AU  - Kamel Alimi
Y1  - 2020/01/04
PY  - 2020
N1  - https://doi.org/10.11648/j.ijctc.20200801.11
DO  - 10.11648/j.ijctc.20200801.11
T2  - International Journal of Computational and Theoretical Chemistry
JF  - International Journal of Computational and Theoretical Chemistry
JO  - International Journal of Computational and Theoretical Chemistry
SP  - 1
EP  - 10
PB  - Science Publishing Group
SN  - 2376-7308
UR  - https://doi.org/10.11648/j.ijctc.20200801.11
AB  - In this paper, geometrical (in ground and excited states), electronic, optical and charge transfer properties, (ionization potentials (IP), electron affinities (EA) and HOMO-LUMO gaps (ΔEH-L), as well as the lowest excitation energies (Eex) and reorganization energies) of the phenylene-tiophene oligomers are studied by the density functional theory (DFT) and Time-dependent DFT approaches. Based on the density functional theory (DFT/B3LYP and CAM –B3LYP functional with 6-31G (d,p) basis set), we will highlight the effect of terminal acceptor/donor (CN, NO2, and CF3) /OCH3, N(CH3)2 substituents on thiophene-phenylene derivatives. The excited state indicates more planar structures of the co-oligomers, which leads to a decrease in the (HOMO-LUMO) gap compared with the ground state, especially when the acceptor character increases. Furthermore, the vinyl spacer and cyanide ((–CN) functional group (Compound C8) stabilize the LUMO levels of energy and improve the transport properties of the thiophene-phenylene derivatives. Comparing with the donor groups, the results show that the electron withdrawing substituents are remarkable on the energy levels of the frontier molecular orbitals, and on the transport charge proprieties in these co-oligomers. Thus, the LUMO energy levels become more stabilized for co-oligomers having more acceptor moieties and the HOMO–LUMO energy gap is reduced, therefore, the improvement of the conduction properties of these species is, then, observed. Moreover, the absorption spectra, computed in the presence or not of solvent at PCM model in chloroform, shows that the increase of acceptor character induces a red shift and important absorption intensity. The decrease injection barrier and smaller reorganization energies are revealing that our designed co-oligomers would be an efficient hole as well as electron transfer materials. The predicted values have shown that the designed derivatives would be efficient for the organic field effect transistors, photovoltaics and light emitters.
VL  - 8
IS  - 1
ER  -

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Author Information

Abdelkader Hlel

Department of Physics, Preparatory Institute for Engineering Studies, University of Monastir, Monastir, Tunisia
Saber Ghomrasni

Department of Physics, Faculty of Sciences, University of Monastir, Monastir, Tunisia
Walid Taouali

Department of Physics, Faculty of Sciences, University of Monastir, Monastir, Tunisia
Kamel Alimi

Department of Physics, Faculty of Sciences, University of Monastir, Monastir, Tunisia

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Abdelkader Hlel, Saber Ghomrasni, Walid Taouali, Kamel Alimi. (2020). Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices. International Journal of Computational and Theoretical Chemistry, 8(1), 1-10. https://doi.org/10.11648/j.ijctc.20200801.11

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ACS Style

Abdelkader Hlel; Saber Ghomrasni; Walid Taouali; Kamel Alimi. Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices. Int. J. Comput. Theor. Chem. 2020, 8(1), 1-10. doi: 10.11648/j.ijctc.20200801.11

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AMA Style

Abdelkader Hlel, Saber Ghomrasni, Walid Taouali, Kamel Alimi. Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices. Int J Comput Theor Chem. 2020;8(1):1-10. doi: 10.11648/j.ijctc.20200801.11

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@article{10.11648/j.ijctc.20200801.11,
  author = {Abdelkader Hlel and Saber Ghomrasni and Walid Taouali and Kamel Alimi},
  title = {Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices},
  journal = {International Journal of Computational and Theoretical Chemistry},
  volume = {8},
  number = {1},
  pages = {1-10},
  doi = {10.11648/j.ijctc.20200801.11},
  url = {https://doi.org/10.11648/j.ijctc.20200801.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijctc.20200801.11},
  abstract = {In this paper, geometrical (in ground and excited states), electronic, optical and charge transfer properties, (ionization potentials (IP), electron affinities (EA) and HOMO-LUMO gaps (ΔEH-L), as well as the lowest excitation energies (Eex) and reorganization energies) of the phenylene-tiophene oligomers are studied by the density functional theory (DFT) and Time-dependent DFT approaches. Based on the density functional theory (DFT/B3LYP and CAM –B3LYP functional with 6-31G (d,p) basis set), we will highlight the effect of terminal acceptor/donor (CN, NO2, and CF3) /OCH3, N(CH3)2 substituents on thiophene-phenylene derivatives. The excited state indicates more planar structures of the co-oligomers, which leads to a decrease in the (HOMO-LUMO) gap compared with the ground state, especially when the acceptor character increases. Furthermore, the vinyl spacer and cyanide ((–CN) functional group (Compound C8) stabilize the LUMO levels of energy and improve the transport properties of the thiophene-phenylene derivatives. Comparing with the donor groups, the results show that the electron withdrawing substituents are remarkable on the energy levels of the frontier molecular orbitals, and on the transport charge proprieties in these co-oligomers. Thus, the LUMO energy levels become more stabilized for co-oligomers having more acceptor moieties and the HOMO–LUMO energy gap is reduced, therefore, the improvement of the conduction properties of these species is, then, observed. Moreover, the absorption spectra, computed in the presence or not of solvent at PCM model in chloroform, shows that the increase of acceptor character induces a red shift and important absorption intensity. The decrease injection barrier and smaller reorganization energies are revealing that our designed co-oligomers would be an efficient hole as well as electron transfer materials. The predicted values have shown that the designed derivatives would be efficient for the organic field effect transistors, photovoltaics and light emitters.},
 year = {2020}
}

Copy | Download

TY  - JOUR
T1  - Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices
AU  - Abdelkader Hlel
AU  - Saber Ghomrasni
AU  - Walid Taouali
AU  - Kamel Alimi
Y1  - 2020/01/04
PY  - 2020
N1  - https://doi.org/10.11648/j.ijctc.20200801.11
DO  - 10.11648/j.ijctc.20200801.11
T2  - International Journal of Computational and Theoretical Chemistry
JF  - International Journal of Computational and Theoretical Chemistry
JO  - International Journal of Computational and Theoretical Chemistry
SP  - 1
EP  - 10
PB  - Science Publishing Group
SN  - 2376-7308
UR  - https://doi.org/10.11648/j.ijctc.20200801.11
AB  - In this paper, geometrical (in ground and excited states), electronic, optical and charge transfer properties, (ionization potentials (IP), electron affinities (EA) and HOMO-LUMO gaps (ΔEH-L), as well as the lowest excitation energies (Eex) and reorganization energies) of the phenylene-tiophene oligomers are studied by the density functional theory (DFT) and Time-dependent DFT approaches. Based on the density functional theory (DFT/B3LYP and CAM –B3LYP functional with 6-31G (d,p) basis set), we will highlight the effect of terminal acceptor/donor (CN, NO2, and CF3) /OCH3, N(CH3)2 substituents on thiophene-phenylene derivatives. The excited state indicates more planar structures of the co-oligomers, which leads to a decrease in the (HOMO-LUMO) gap compared with the ground state, especially when the acceptor character increases. Furthermore, the vinyl spacer and cyanide ((–CN) functional group (Compound C8) stabilize the LUMO levels of energy and improve the transport properties of the thiophene-phenylene derivatives. Comparing with the donor groups, the results show that the electron withdrawing substituents are remarkable on the energy levels of the frontier molecular orbitals, and on the transport charge proprieties in these co-oligomers. Thus, the LUMO energy levels become more stabilized for co-oligomers having more acceptor moieties and the HOMO–LUMO energy gap is reduced, therefore, the improvement of the conduction properties of these species is, then, observed. Moreover, the absorption spectra, computed in the presence or not of solvent at PCM model in chloroform, shows that the increase of acceptor character induces a red shift and important absorption intensity. The decrease injection barrier and smaller reorganization energies are revealing that our designed co-oligomers would be an efficient hole as well as electron transfer materials. The predicted values have shown that the designed derivatives would be efficient for the organic field effect transistors, photovoltaics and light emitters.
VL  - 8
IS  - 1
ER  -

Copy | Download