Indolocarbazole (IC) Derivatives as Promising p‐type Organic Semiconductors: A First‐Principle Study of Their Anisotropic Charge Mobilities

Abstract

We present a detailed theoretical study of the structural, charge transport, and optical properties of three indolocarbazole derivatives, viz., 11, 12‐Dihydroindolo[2, 3‐a]carbazole (DIC), 5, 10‐dimethyl‐5,10‐dihydrobenzo[a]indolo[2, 3‐c]carbazole (DMDBIC), and 2,11‐dimethoxydibenzo[2, 3:5,6]pyrrolizino[1, 7‐bc]indolo[1, 2,3‐lm]carbazole (DMDPIC). DFT calculations along with previously reported x‐ray crystal structures reveal that the studied compounds are planar and do not undergo significant changes in structure upon oxidation or reduction. The maximum hole anisotropic charge mobilities for DIC was found to be 0.338 cm2 V−1 s−1 at Φ=175.89° and 355.81° and the maximum electron mobility was 0.181 cm2 V−1 s−1 at Φ=85.94° and 265.85°. For DMDBIC, the predicted maximum anisotropic hole, and electron mobility was 0.501 cm2 V−1 s−1 and 0.775 cm2 V−1 s−1, respectively at Φ=56.72° and 236.63°, while for DMDPIC the predicted maximum anisotropic hole and electron mobility as 1.586 cm2 V−1 s−1 and 0.594 cm2 V−1 s−1, respectively at Φ=0° and 180.0°. The calculated mobilities show that these compounds may be suitable candidates as a p‐type organic semiconductor with better stability than acene compounds.

Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi‐Walled Carbon Nanotubes in Liquid Phase

“…Interestingly, 3c required av ery long reaction time and after sixd ays, 29 %y ield was obtained together with 60 %o f unreacteds tartingm aterial. To our pleasure, 4d,w hich has been indicated as potential substructure for p-type organic semiconductors [33] and promising framework for optoelectronic applications, [34] was obtained in an 84 %y ield. Similarly, 4f,a substructure found in molecules with interesting chiroptical properties fora pplicationss uch as,f or example, spintronic devices, [35] was obtained in 82 %yield.…”

Computational Design of Crescent Shaped Promising Nonfullerene Acceptors with 1,4-Dihydro-2,3-quinoxalinedione Core and Different Electron-withdrawing Terminal Units for Photovoltaic Applications

“…Based on the predicted crystal structures, we have used nearest neighbor approximation via considering one molecule in a crystal as the center, and its adjacent parallel dimers. Those distinct nearest parallel dimers are selected as charge hopping pathways. − The θ’s in Figure (a) are the angles of the hopping pathways relative to the crystallographic axis ( b -axis). The D1, D2, ..., D8 are the intermolecular distances associated with different hopping pathways and ϕ is the angle of orientation of the conducting channel (indicated by black colored line) relative to the crystallographic axis ( b -axis).…”

“…The computed charge transport parameters along different hopping dimers and charge carrier mobilities of the studied NFAs are listed in Table and Table . In organic crystals, different molecular packing motifs along dissimilar hopping pathways and the variation in the charge transfer integrals of the central molecule with the adjacent molecules produces angular dependence of mobility, that is, anisotropic mobility. − The anisotropic mobility (μ ϕ ) of the studied NFAs are evaluated using the formulation as described in section S.2.4 in the Supporting Information. The anisotropic electron/hole mobilities (μ e /μ h ) of a subset of the studied NFAs are shown in Figure , while the plots for all other NFAs are available in Figures S10–S12 in the Supporting Information.…”

Theoretical Studies on Novel Gridspiroarenes: Structures, Noncovalent Interactions and Reorganization Energies

“…Hence, it is necessary to study organic semiconductors with excellent charge transfer properties. Theoretical approaches have been an important way for designing a new class of organic optoelectronic materials …”