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

Viktorija Mimaite, Juozas Vidas Grazulevicius, Rasa Laurinaviciute, Dmytro Volyniuk, Vygintas Jankauskas, Gjergji Sini

Research output: Contribution to journalArticlepeer-review

49 Scopus citations


© 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.
Original languageEnglish (US)
Pages (from-to)11660-11674
Number of pages15
JournalJ. Mater. Chem. C
Issue number44
StatePublished - 2015
Externally publishedYes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.


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