Next Article in Journal
Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers
Previous Article in Journal
4-Phenethyl-1-Propargylpiperidine-Derived Dual Inhibitors of Butyrylcholinesterase and Monoamine Oxidase B
Previous Article in Special Issue
A Computational Protocol Combining DFT and Cheminformatics for Prediction of pH-Dependent Redox Potentials
Article

Impact of Fluoroalkylation on the n-Type Charge Transport of Two Naphthodithiophene Diimide Derivatives

by 1,†, 1,‡, 1, 2,* and 1,3,*
1
Dipartimento di Chimica “Giacomo Ciamician”, Università di Bologna, Via F. Selmi, 2, 40126 Bologna, Italy
2
Institut für Physikalische Chemie, Department für Chemie, Universität zu Köln, Greinstr. 4-6, D-50939 Köln, Germany
3
INSTM, UdR Bologna, Via F. Selmi, 2, 40126 Bologna, Italy
*
Authors to whom correspondence should be addressed.
Present address: Unité de Chimie Physique Théorique et Structurale & Laboratoire de Physique du Solide, Namur Institute of Structured Matter, Université de Namur, B-5000 Namur, Belgium.
Present address: Institute of Physics, Czech Academy of Sciences, Cukrovarnická 10/112, CZ16200 Praha 6, Czech Republic.
Academic Editor: Daniele Padula
Molecules 2021, 26(14), 4119; https://doi.org/10.3390/molecules26144119
Received: 11 June 2021 / Revised: 3 July 2021 / Accepted: 4 July 2021 / Published: 6 July 2021
In this work, we investigate two recently synthesized naphthodithiophene diimide (NDTI) derivatives featuring promising n-type charge transport properties. We analyze the charge transport pathways and model charge mobility with the non-adiabatic hopping mechanism using the Marcus-Levich-Jortner rate constant formulation, highlighting the role of fluoroalkylated substitution in α (α-NDTI) and at the imide nitrogen (N-NDTI) position. In contrast with the experimental results, similar charge mobilities are computed for the two derivatives. However, while α-NDTI displays remarkably anisotropic mobilities with an almost one-dimensional directionality, N-NDTI sustains a more isotropic charge percolation pattern. We propose that the strong anisotropic charge transport character of α-NDTI is responsible for the modest measured charge mobility. In addition, when the role of thermally induced transfer integral fluctuations is investigated, the computed electron–phonon couplings for intermolecular sliding modes indicate that dynamic disorder effects are also more detrimental for the charge transport of α-NDTI than N-NDTI. The lower observed mobility of α-NDTI is therefore rationalized in terms of a prominent anisotropic character of the charge percolation pathways, with the additional contribution of dynamic disorder effects. View Full-Text
Keywords: n-type; organic semiconductors; charge transport; organic crystals; charge mobility anisotropy; charge transfer; quantum chemistry; DFT; dynamic disorder; electron-phonon coupling n-type; organic semiconductors; charge transport; organic crystals; charge mobility anisotropy; charge transfer; quantum chemistry; DFT; dynamic disorder; electron-phonon coupling
Show Figures

Figure 1

MDPI and ACS Style

Ricci, G.; Canola, S.; Dai, Y.; Fazzi, D.; Negri, F. Impact of Fluoroalkylation on the n-Type Charge Transport of Two Naphthodithiophene Diimide Derivatives. Molecules 2021, 26, 4119. https://doi.org/10.3390/molecules26144119

AMA Style

Ricci G, Canola S, Dai Y, Fazzi D, Negri F. Impact of Fluoroalkylation on the n-Type Charge Transport of Two Naphthodithiophene Diimide Derivatives. Molecules. 2021; 26(14):4119. https://doi.org/10.3390/molecules26144119

Chicago/Turabian Style

Ricci, Gaetano, Sofia Canola, Yasi Dai, Daniele Fazzi, and Fabrizia Negri. 2021. "Impact of Fluoroalkylation on the n-Type Charge Transport of Two Naphthodithiophene Diimide Derivatives" Molecules 26, no. 14: 4119. https://doi.org/10.3390/molecules26144119

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop