Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy

The present study spotlights the designing of new derivatives of 2,7-bis (4-octylphenyl) naphtho [2,1-b:6,5-b'] difuran (C8-DPNDF) by substituting the alkyl groups (methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl groups) at para position. Density functional theory (DFT) and time-depende...

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Main Authors: Chaudhry, Aijaz Rasool, Ahmed, R., Irfan, Ahmad, Shaari, A., Isa, A. R., Muhammad, S., Al-Sehemi, A G.
Format: Article
Published: Springer Verlag 2015
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Online Access:http://eprints.utm.my/id/eprint/58365/
http://dx.doi.org/10.1007/s00894-015-2743-9
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spelling my.utm.583652021-12-14T05:09:38Z http://eprints.utm.my/id/eprint/58365/ Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy Chaudhry, Aijaz Rasool Ahmed, R. Irfan, Ahmad Shaari, A. Isa, A. R. Muhammad, S. Al-Sehemi, A G. QC Physics The present study spotlights the designing of new derivatives of 2,7-bis (4-octylphenyl) naphtho [2,1-b:6,5-b'] difuran (C8-DPNDF) by substituting the alkyl groups (methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl groups) at para position. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods are employed to optimize the molecular structures in ground and first excited states, respectively. Several electro-optical properties including hole/electron reorganization energies (?h/?e), electron affinities (EAs), ionization potentials (IPs), molecular electrostatic potentials (MEP), and frontier molecular orbitals (FMOs) have been evaluated. Furthermore their transfer integrals and intrinsic mobilities values have also been calculated. From this study, it is found that hole mobility of octyl containing derivative is raised to 4.69 cm2 V-1 s-1. Moreover with attaching octyl group, hole transfer integral values have also been enhanced in newly designed derivatives. The balanced hole and electron reorganization energies, and improved transfer integrals lead to enhanced mobility in derivatives with octyl group, highlighting them as an efficient hole transfer material. Unlike the other electro-optical properties, the intrinsic hole mobility has increased because of transfer integral values of octyl containing derivative C8-DPNDF due to the dense and close crystal packing of C8-DPNDF. However, photostability of furan-based materials has not changed by increasing length of extended alkyl chain. Thus our present investigation highlights the importance of alkyl auxiliary groups that are often neglected/replaced with simple methyl group to save computation costs. Springer Verlag 2015 Article PeerReviewed Chaudhry, Aijaz Rasool and Ahmed, R. and Irfan, Ahmad and Shaari, A. and Isa, A. R. and Muhammad, S. and Al-Sehemi, A G. (2015) Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy. Journal of Molecular Modeling, 21 (8). p. 199. ISSN 1610-2940 http://dx.doi.org/10.1007/s00894-015-2743-9 DOI:10.1007/s00894-015-2743-9
institution Universiti Teknologi Malaysia
building UTM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Malaysia
content_source UTM Institutional Repository
url_provider http://eprints.utm.my/
topic QC Physics
spellingShingle QC Physics
Chaudhry, Aijaz Rasool
Ahmed, R.
Irfan, Ahmad
Shaari, A.
Isa, A. R.
Muhammad, S.
Al-Sehemi, A G.
Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy
description The present study spotlights the designing of new derivatives of 2,7-bis (4-octylphenyl) naphtho [2,1-b:6,5-b'] difuran (C8-DPNDF) by substituting the alkyl groups (methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl groups) at para position. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods are employed to optimize the molecular structures in ground and first excited states, respectively. Several electro-optical properties including hole/electron reorganization energies (?h/?e), electron affinities (EAs), ionization potentials (IPs), molecular electrostatic potentials (MEP), and frontier molecular orbitals (FMOs) have been evaluated. Furthermore their transfer integrals and intrinsic mobilities values have also been calculated. From this study, it is found that hole mobility of octyl containing derivative is raised to 4.69 cm2 V-1 s-1. Moreover with attaching octyl group, hole transfer integral values have also been enhanced in newly designed derivatives. The balanced hole and electron reorganization energies, and improved transfer integrals lead to enhanced mobility in derivatives with octyl group, highlighting them as an efficient hole transfer material. Unlike the other electro-optical properties, the intrinsic hole mobility has increased because of transfer integral values of octyl containing derivative C8-DPNDF due to the dense and close crystal packing of C8-DPNDF. However, photostability of furan-based materials has not changed by increasing length of extended alkyl chain. Thus our present investigation highlights the importance of alkyl auxiliary groups that are often neglected/replaced with simple methyl group to save computation costs.
format Article
author Chaudhry, Aijaz Rasool
Ahmed, R.
Irfan, Ahmad
Shaari, A.
Isa, A. R.
Muhammad, S.
Al-Sehemi, A G.
author_facet Chaudhry, Aijaz Rasool
Ahmed, R.
Irfan, Ahmad
Shaari, A.
Isa, A. R.
Muhammad, S.
Al-Sehemi, A G.
author_sort Chaudhry, Aijaz Rasool
title Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy
title_short Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy
title_full Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy
title_fullStr Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy
title_full_unstemmed Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy
title_sort effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy
publisher Springer Verlag
publishDate 2015
url http://eprints.utm.my/id/eprint/58365/
http://dx.doi.org/10.1007/s00894-015-2743-9
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score 13.211869