Can hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insights

Handle URI:
http://hdl.handle.net/10754/597718
Title:
Can hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insights
Authors:
Mimaite, Viktorija; Grazulevicius, Juozas Vidas; Laurinaviciute, Rasa; Volyniuk, Dmytro; Jankauskas, Vygintas; Sini, Gjergji
Abstract:
© The Royal Society of Chemistry 2015. Five hole-transporting triphenylamine derivatives containing methoxy and methyl groups are synthesized and investigated. The hole-mobility increases in the presence of methyl and methoxy substituents, exceeding 10-2 cm2 V-1 s-1 in the case of methyl groups. Quantum mechanical calculations on these compounds indicate very different dipole moments and intermolecular interaction strengths, with intriguing correlations with the trend in hole-mobility. Temperature dependent hole-mobility measurements indicate disorder dominated hole transport. The values of the energetic disorder parameter (σ) decrease upon methyl and methoxy substitutions despite the increase in dipole moments. This trend is discussed as a function of the interaction energy between adjacent molecules, the dipole moment, the molecular polarizability, and the conformational degree of freedom. Our results indicate that the global decrease of σ upon methyl and methoxy substitutions is dominated by the larger decrease in the geometrical randomness component of the energetic disorder. A direct correlation is established between the decrease in geometrical randomness and the increase in intermolecular interaction energies, mainly stemming from the additional C-H⋯π, O, N hydrogen bonds induced by methyl and methoxy groups.
Citation:
Mimaite V, Grazulevicius JV, Laurinaviciute R, Volyniuk D, Jankauskas V, et al. (2015) Can hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insights. J Mater Chem C 3: 11660–11674. Available: http://dx.doi.org/10.1039/c5tc02534f.
Publisher:
Royal Society of Chemistry (RSC)
Journal:
J. Mater. Chem. C
Issue Date:
2015
DOI:
10.1039/c5tc02534f
Type:
Article
ISSN:
2050-7526; 2050-7534
Sponsors:
This work has been financially supported by the Taiwan–Latvia–Lithuania cooperation project “Synthesis and studies of organic electroactive materials for effective and reliable optoelectronic devices” (TAPLLT1/13). G.S. acknowledges the calculation centre of Cergy-Pontoise University for the computer time support, and V. Coropceanu and B. Kippelen (Georgia Tech', Atlanta, Georgia, USA), M. K. Ravva (KAUST, Saudi Arabia), and V. Cobut (Cergy-Pontoise University, France) for stimulating.
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Full metadata record

DC FieldValue Language
dc.contributor.authorMimaite, Viktorijaen
dc.contributor.authorGrazulevicius, Juozas Vidasen
dc.contributor.authorLaurinaviciute, Rasaen
dc.contributor.authorVolyniuk, Dmytroen
dc.contributor.authorJankauskas, Vygintasen
dc.contributor.authorSini, Gjergjien
dc.date.accessioned2016-02-25T12:55:27Zen
dc.date.available2016-02-25T12:55:27Zen
dc.date.issued2015en
dc.identifier.citationMimaite V, Grazulevicius JV, Laurinaviciute R, Volyniuk D, Jankauskas V, et al. (2015) Can hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insights. J Mater Chem C 3: 11660–11674. Available: http://dx.doi.org/10.1039/c5tc02534f.en
dc.identifier.issn2050-7526en
dc.identifier.issn2050-7534en
dc.identifier.doi10.1039/c5tc02534fen
dc.identifier.urihttp://hdl.handle.net/10754/597718en
dc.description.abstract© The Royal Society of Chemistry 2015. Five hole-transporting triphenylamine derivatives containing methoxy and methyl groups are synthesized and investigated. The hole-mobility increases in the presence of methyl and methoxy substituents, exceeding 10-2 cm2 V-1 s-1 in the case of methyl groups. Quantum mechanical calculations on these compounds indicate very different dipole moments and intermolecular interaction strengths, with intriguing correlations with the trend in hole-mobility. Temperature dependent hole-mobility measurements indicate disorder dominated hole transport. The values of the energetic disorder parameter (σ) decrease upon methyl and methoxy substitutions despite the increase in dipole moments. This trend is discussed as a function of the interaction energy between adjacent molecules, the dipole moment, the molecular polarizability, and the conformational degree of freedom. Our results indicate that the global decrease of σ upon methyl and methoxy substitutions is dominated by the larger decrease in the geometrical randomness component of the energetic disorder. A direct correlation is established between the decrease in geometrical randomness and the increase in intermolecular interaction energies, mainly stemming from the additional C-H⋯π, O, N hydrogen bonds induced by methyl and methoxy groups.en
dc.description.sponsorshipThis work has been financially supported by the Taiwan–Latvia–Lithuania cooperation project “Synthesis and studies of organic electroactive materials for effective and reliable optoelectronic devices” (TAPLLT1/13). G.S. acknowledges the calculation centre of Cergy-Pontoise University for the computer time support, and V. Coropceanu and B. Kippelen (Georgia Tech', Atlanta, Georgia, USA), M. K. Ravva (KAUST, Saudi Arabia), and V. Cobut (Cergy-Pontoise University, France) for stimulating.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleCan hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insightsen
dc.typeArticleen
dc.identifier.journalJ. Mater. Chem. Cen
dc.contributor.institutionKaunas University of Technology, Kaunas, Lithuaniaen
dc.contributor.institutionVilnius University, Vilnius, Lithuaniaen
dc.contributor.institutionUniversite de Cergy-Pontoise, Cergy-Pontoise, Franceen
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